NCBI Taxonomy: 429256

Carissa spinarum (ncbi_taxid: 429256)

found 181 associated metabolites at species taxonomy rank level.

Ancestor: Carissa

Child Taxonomies: none taxonomy data.

Scopoletin

7-hydroxy-6-methoxy-2H-chromen-2-one

C10H8O4 (192.0422568)


Scopoletin is a hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. It has a role as a plant growth regulator and a plant metabolite. It is functionally related to an umbelliferone. Scopoletin is a natural product found in Ficus auriculata, Haplophyllum cappadocicum, and other organisms with data available. Scopoletin is a coumarin compound found in several plants including those in the genus Scopolia and the genus Brunfelsia, as well as chicory (Cichorium), redstem wormwood (Artemisia scoparia), stinging nettle (Urtica dioica), passion flower (Passiflora), noni (Morinda citrifolia fruit) and European black nightshade (Solanum nigrum) that is comprised of umbelliferone with a methoxy group substituent at position 6. Scopoletin is used to standardize and establish pharmacokinetic properties for products derived from the plants that produce it, such as noni extract. Although the mechanism(s) of action have not yet been established, this agent has potential antineoplastic, antidopaminergic, antioxidant, anti-inflammatory and anticholinesterase effects. Plant growth factor derived from the root of Scopolia carniolica or Scopolia japonica. See also: Arnica montana Flower (part of); Lycium barbarum fruit (part of); Viburnum opulus root (part of). Isolated from Angelica acutiloba (Dong Dang Gui). Scopoletin is found in many foods, some of which are lambsquarters, lemon, sunflower, and sherry. Scopoletin is found in anise. Scopoletin is isolated from Angelica acutiloba (Dong Dang Gui A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA72_Scopoletin_pos_20eV.txt [Raw Data] CBA72_Scopoletin_pos_40eV.txt [Raw Data] CBA72_Scopoletin_neg_30eV.txt [Raw Data] CBA72_Scopoletin_neg_50eV.txt [Raw Data] CBA72_Scopoletin_pos_50eV.txt [Raw Data] CBA72_Scopoletin_pos_10eV.txt [Raw Data] CBA72_Scopoletin_neg_40eV.txt [Raw Data] CBA72_Scopoletin_neg_10eV.txt [Raw Data] CBA72_Scopoletin_pos_30eV.txt [Raw Data] CBA72_Scopoletin_neg_20eV.txt Scopoletin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=92-61-5 (retrieved 2024-07-12) (CAS RN: 92-61-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

Vanillin

Vanillin melting point standard, Pharmaceutical Secondary Standard; Certified Reference Material

C8H8O3 (152.0473418)


Vanillin, also known as vanillaldehyde or lioxin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is used by the food industry as well as ethylvanillin. Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns, ryes, and sherries and in a lower concentration in beers, rums, and oats. Vanillin has also been detected, but not quantified, in several different foods, such as gooseberries, other bread, brazil nuts, shea tree, and ohelo berries. This could make vanillin a potential biomarker for the consumption of these foods. Vanillin is a potentially toxic compound. Synthetic vanillin, instead of natural Vanillin extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanillin bean. Because of the scarcity and expense of natural Vanillin extract, there has long been interest in the synthetic preparation of its predominant component. Artificial Vanillin flavoring is a solution of pure vanillin, usually of synthetic origin. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Vanillin appears as white or very slightly yellow needles. Vanillin is a member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. It has a role as a plant metabolite, an anti-inflammatory agent, a flavouring agent, an antioxidant and an anticonvulsant. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes. Vanillin is a natural product found in Ficus erecta var. beecheyana, Pandanus utilis, and other organisms with data available. Vanillin is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. It is used by the food industry as well as ethylvanillin.Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. (Wiki). Vanillin is a metabolite found in or produced by Saccharomyces cerevisiae. Constituent of vanilla (Vanilla subspecies) and many other plants, e.g. Peru balsam, clove bud oil. Widely used flavouring agent especies in cocoa products. obtained from spent wood-pulp liquors. Vanillin is found in many foods, some of which are pomes, elderberry, common cabbage, and dock. A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; ML_ID 59 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

   

Isofraxidin

7-Hydroxy-6,8-dimethoxy-2H-1-benzopyran-2-one

C11H10O5 (222.052821)


Isofraxidin, also known as 6,8-dimethoxy-7-hydroxycoumarin or 7-hydroxy-6,8-dimethoxy-2h-1-benzopyran-2-one, is a member of the class of compounds known as 7-hydroxycoumarins. 7-hydroxycoumarins are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Isofraxidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isofraxidin can be found in muskmelon, tarragon, and watermelon, which makes isofraxidin a potential biomarker for the consumption of these food products. Isofraxidin is a chemical compound found in a variety of plants including Eleutherococcus senticosus . Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2]. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2].

   

Coniferaldehyde

(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal

C10H10O3 (178.062991)


Coniferaldehyde (CAS: 458-36-6), also known as 4-hydroxy-3-methoxycinnamaldehyde or ferulaldehyde, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, coniferaldehyde is found, on average, in the highest concentration within sherries. Coniferaldehyde has also been detected, but not quantified in, several different foods, such as highbush blueberries, lima beans, Chinese cabbages, loquats, and greenthread tea. This could make coniferaldehyde a potential biomarker for the consumption of these foods. BioTransformer predicts that coniferaldehyde is a product of caffeic aldehyde metabolism via a catechol-O-methylation-pattern2 reaction catalyzed by the enzyme catechol O-methyltransferase (PMID: 30612223). Coniferyl aldehyde, also known as 4-hydroxy-3-methoxycinnamaldehyde or 4-hm-ca, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferyl aldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Coniferyl aldehyde can be found in a number of food items such as pear, common walnut, kelp, and citrus, which makes coniferyl aldehyde a potential biomarker for the consumption of these food products. Coniferyl aldehyde is a low molecular weight phenolic compound susceptible to be extracted from cork stoppers into wine . Coniferyl aldehyde is a member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as an antifungal agent and a plant metabolite. It is a member of cinnamaldehydes, a phenylpropanoid and a member of guaiacols. It is functionally related to an (E)-cinnamaldehyde. 4-Hydroxy-3-methoxycinnamaldehyde is a natural product found in Pandanus utilis, Microtropis japonica, and other organisms with data available. A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. Acquisition and generation of the data is financially supported in part by CREST/JST. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1]. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells Coniferaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=458-36-6 (retrieved 2024-09-04) (CAS RN: 458-36-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Beta-eudesmol

2-Naphthalenemethanol, 1,2.alpha.,3,4,4a,5,6,7,8,8a.alpha.-decahydro-.alpha.,.alpha.,4a.beta.-trimethyl-8-methylene-

C15H26O (222.1983546)


Beta-eudesmol is a carbobicyclic compound that is trans-decalin substituted at positions 2, 4a, and 8 by 2-hydroxypropan-2-yl, methyl and methylidene groups, respectively (the 2R,4aR,8aS-diastereoisomer). It has a role as a volatile oil component. It is a carbobicyclic compound, a tertiary alcohol and a eudesmane sesquiterpenoid. beta-Eudesmol is a natural product found in Rhododendron calostrotum, Rhododendron lepidotum, and other organisms with data available. See also: Arctium lappa Root (part of); Cannabis sativa subsp. indica top (part of); Pterocarpus marsupium wood (part of). A carbobicyclic compound that is trans-decalin substituted at positions 2, 4a, and 8 by 2-hydroxypropan-2-yl, methyl and methylidene groups, respectively (the 2R,4aR,8aS-diastereoisomer). Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1]. Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1].

   

Secoisolariciresinol

1,4-Butanediol, 2,3-bis((4-hydroxy-3-methoxyphenyl)methyl)-, (R-(R*,R*))-

C20H26O6 (362.17292960000003)


Secoisolariciresinol, also known as knotolan or secoisolariciresinol, (r*,s*)-isomer, is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as grape, saskatoon berry, asparagus, and sweet potato, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol can be found primarily in urine. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 \\\\% . (-)-secoisolariciresinol is an enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration. It has a role as an antidepressant, a plant metabolite and a phytoestrogen. It is an enantiomer of a (+)-secoisolariciresinol. Secoisolariciresinol has been used in trials studying the prevention of Breast Cancer. Secoisolariciresinol is a natural product found in Fitzroya cupressoides, Crossosoma bigelovii, and other organisms with data available. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids.

   

SS-secoisolariciresinol

1,4-Butanediol, 2,3-bis((4-hydroxy-3-methoxyphenyl)methyl)-, (S-(R*,R*))-

C20H26O6 (362.17292960000003)


(+)-secoisolariciresinol is an enantiomer of secoisolariciresinol having (+)-(2S,3S)-configuration. It is an enantiomer of a (-)-secoisolariciresinol. (+)-Secoisolariciresinol is a natural product found in Taxus baccata, Phyllanthus polyphyllus, and other organisms with data available. An enantiomer of secoisolariciresinol having (+)-(2S,3S)-configuration. (+)-Secoisolariciresinol, a lignan compound, is a (+)-enantiomer of Secoisolariciresinol[1].

   

2-Hydroxyacetophenone

2-Hydroxy-1-phenylethan-1-one

C8H8O2 (136.0524268)


2-Hydroxyacetophenone is a principal root volatile of the Carissa edulis[1]. 2-Hydroxyacetophenone shows inhibitory effects on infection of HIV/SARS-CoV S pseudovirus with an IC50 of 1.8 mM[2]. 2-Hydroxyacetophenone is a principal root volatile of the Carissa edulis[1]. 2-Hydroxyacetophenone shows inhibitory effects on infection of HIV/SARS-CoV S pseudovirus with an IC50 of 1.8 mM[2].

   

(-)-Wikstromol

dihydro-3-hydroxy-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-2(3H)-furanone

C20H22O7 (374.1365462)


(-)-Wikstromol is found in fruits. (-)-Wikstromol is obtained from Pinus palustris (pitch pine) and Carissa edulis (agam obtained from Pinus palustris (pitch pine) and Carissa edulis (agam). (-)-Wikstromol is found in fruits and sesame.

   

Proximadiol

2-Naphthalenemethanol, decahydro-8-hydroxy-alpha,alpha,4a,8-tetramethyl-, (2R-(2alpha,4aalpha,8beta,8abeta))-

C15H28O2 (240.20891880000002)


   

(-)-lariciresinol

(-)-lariciresinol

C20H24O6 (360.1572804)


A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2R,3S,4S-diastereomer).

   

Isofraxidin

7-hydroxy-6,8-dimethoxy-chromen-2-one;Isofraxidin

C11H10O5 (222.052821)


Isofraxidin is a hydroxycoumarin. Isofraxidin is a natural product found in Artemisia alba, Artemisia assoana, and other organisms with data available. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2]. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2].

   

AI3-15121

InChI=1/C8H8O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,9H,6H

C8H8O2 (136.0524268)


2-hydroxyacetophenone is a monohydroxyacetophenone that is acetophenone in which one of the methyl hydrogens has been replaced by a hydroxy group. It is a primary alcohol, a primary alpha-hydroxy ketone and a monohydroxyacetophenone. 2-Hydroxyacetophenone is a natural product found in Carissa spinarum, Scutellaria baicalensis, and Carissa edulis with data available. 2-Hydroxyacetophenone is a principal root volatile of the Carissa edulis[1]. 2-Hydroxyacetophenone shows inhibitory effects on infection of HIV/SARS-CoV S pseudovirus with an IC50 of 1.8 mM[2]. 2-Hydroxyacetophenone is a principal root volatile of the Carissa edulis[1]. 2-Hydroxyacetophenone shows inhibitory effects on infection of HIV/SARS-CoV S pseudovirus with an IC50 of 1.8 mM[2].

   

2'-Hydroxyacetophenone

1-(2-Hydroxyphenyl)ethanone; Paracetamol Imp. I (EP); 2-Hydroxyacetophenone; Paracetamol Impurity I

C8H8O2 (136.0524268)


2-Hydroxyacetophenone, also known as 2-acetylphenol or 2-hydroxyacetylbenzene, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2-Hydroxyacetophenone is a sweet, hawthorne, and herbal tasting compound. 2-hydroxyacetophenone has been detected, but not quantified, in several different foods, such as chinese cinnamons, tea, coffee and coffee products, alcoholic beverages, and garden tomato. 2-acetylphenol is a monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group. It has a role as a flavouring agent. It is a monohydroxyacetophenone and a member of phenols. 2-Hydroxyacetophenone is a natural product found in Castanopsis cuspidata, Mangifera indica, and other organisms with data available. Present in tomato, cassia (Cinnamomum cassia), fried beef, rum, whiskey, cocoa, coffee and black tea. Flavouring ingredient. 2-Hydroxyacetophenone is found in many foods, some of which are garden tomato, tea, chinese cinnamon, and herbs and spices. 2'-Hydroxyacetophenone is found in alcoholic beverages. 2'-Hydroxyacetophenone is present in tomato, cassia, fried beef, rum, whiskey, cocoa, coffee and black tea. 2'-Hydroxyacetophenone is a flavouring ingredient. Building block in chemical synthesis. 2'-Hydroxyacetophenone is found in alcoholic beverages. 2'-Hydroxyacetophenone is present in tomato, cassia, fried beef, rum, whiskey, cocoa, coffee and black tea. 2'-Hydroxyacetophenone is a flavouring ingredient. Building block in chemical synthesis.

   

3-Hydroxy-1-(4-hydroxyphenyl)-1-propanone

3-Hydroxy-1-(4-hydroxyphenyl)-1-propanone

C9H10O3 (166.062991)


3-Hydroxy-1-(4-hydroxyphenyl)-1-propanone is found in fruits. 3-Hydroxy-1-(4-hydroxyphenyl)-1-propanone is a constituent of Carissa edulis (agam). Constituent of Carissa edulis (agam). 3-Hydroxy-1-(4-hydroxyphenyl)-1-propanone is found in fruits.

   

Carissanol

Tetrahydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2,3-furandiol, 9ci

C20H24O7 (376.1521954)


Carissanol is found in fruits. Carissanol is a constituent of Carissa edulis (agam)

   

Germacrenone

(3Z)-7-(2-hydroxypropan-2-yl)-4,10-dimethylcyclodec-3-en-1-one

C15H26O2 (238.1932696)


Germacrenone is found in fruits. Germacrenone is a constituent of Carissa edulis (agam) Constituent of Carissa edulis (agam). Germacrenone is found in fruits.

   

Flaxseeds extract

2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

C20H26O6 (362.17292960000003)


Secoisolariciresinol is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as barley, wheat bread, broad bean, and poppy, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 \\% .

   

Lariciresinol

4-{4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-2-methoxyphenol

C20H24O6 (360.1572804)


(-)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as cassava, acorn, celeriac, and banana, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products.

   

L-Olivil

5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-3-ol

C20H24O7 (376.1521954)


L-olivil is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. L-olivil is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). L-olivil can be found in olive, which makes L-olivil a potential biomarker for the consumption of this food product.

   

β-Eudesmol

beta-Eudesmol

C15H26O (222.1983546)


Beta-eudesmol, also known as beta-selinenol, is a member of the class of compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids are sesquiterpenoids with a structure based on the eudesmane skeleton. Beta-eudesmol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-eudesmol is a green and wood tasting compound and can be found in a number of food items such as common walnut, sweet basil, ginkgo nuts, and burdock, which makes beta-eudesmol a potential biomarker for the consumption of these food products. Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1]. Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1].

   

Vanillin

4-hydroxy-3-methoxybenzaldehyde

C8H8O3 (152.0473418)


CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3579; ORIGINAL_PRECURSOR_SCAN_NO 3578 D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3566; ORIGINAL_PRECURSOR_SCAN_NO 3561 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3549; ORIGINAL_PRECURSOR_SCAN_NO 3546 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3560; ORIGINAL_PRECURSOR_SCAN_NO 3556 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3573; ORIGINAL_PRECURSOR_SCAN_NO 3570 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3577; ORIGINAL_PRECURSOR_SCAN_NO 3575 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.504 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.503 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.500 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

   

coniferyl aldehyde

4-Hydroxy-3-methoxy-trans-cinnamaldehyde

C10H10O3 (178.062991)


Annotation level-1 Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1]. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1].

   

wikstromol

2(3H)-Furanone, dihydro-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-3-hydroxy-, (3R-cis)-

C20H22O7 (374.1365462)


Nortrachelogenin is a lignan. Nortrachelogenin is a natural product found in Passerina corymbosa, Didymochlaena truncatula, and other organisms with data available. (+)-Nortrachelogenin is a natural product found in Carissa carandas, Daphne oleoides, and other organisms with data available.

   

Scopoletin

Scopoletin

C10H8O4 (192.0422568)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.637 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.629 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.631 IPB_RECORD: 1582; CONFIDENCE confident structure Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

Isofraxidin

Isofraxidin

C11H10O5 (222.052821)


Annotation level-1 Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2]. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2].

   

Secoisolariciresinol

(-)-Secoisolariciresinol

C20H26O6 (362.17292960000003)


Annotation level-1 D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens relative retention time with respect to 9-anthracene Carboxylic Acid is 0.816 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.813 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.806 Secoisolariciresinol is a lignan, a type of phenylpropanoids. Secoisolariciresinol is a lignan, a type of phenylpropanoids.

   

3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

NCGC00180383-02!3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

C20H22O7 (374.1365462)


   

2-Hydroxyacetophenone

2-Hydroxyacetophenone

C8H8O2 (136.0524268)


   

3-hydroxy-1-(4-hydroxyphenyl)propan-1-one

3-hydroxy-1-(4-hydroxyphenyl)propan-1-one

C9H10O3 (166.062991)


   

2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

C20H26O6 (362.17292960000003)


   

coniferaldehyde

coniferaldehyde

C10H10O3 (178.062991)


CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 13

   

CARISSANOL

Tetrahydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2,3-furandiol, 9ci

C20H24O7 (376.1521954)


   

Glycolophenone

Acetophenone, 2'-hydroxy- (8CI)

C8H8O2 (136.0524268)


2'-Hydroxyacetophenone is found in alcoholic beverages. 2'-Hydroxyacetophenone is present in tomato, cassia, fried beef, rum, whiskey, cocoa, coffee and black tea. 2'-Hydroxyacetophenone is a flavouring ingredient. Building block in chemical synthesis. 2'-Hydroxyacetophenone is found in alcoholic beverages. 2'-Hydroxyacetophenone is present in tomato, cassia, fried beef, rum, whiskey, cocoa, coffee and black tea. 2'-Hydroxyacetophenone is a flavouring ingredient. Building block in chemical synthesis.

   

germacrenone

(3Z)-7-(2-hydroxypropan-2-yl)-4,10-dimethylcyclodec-3-en-1-one

C15H26O2 (238.1932696)


   

3,4'-Dihydroxypropiophenone

3-Hydroxy-1-(4-hydroxyphenyl)-1-propanone

C9H10O3 (166.062991)


   

473-15-4

InChI=1\C15H26O\c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16\h12-13,16H,1,5-10H2,2-4H3\t12-,13+,15-\m1\s

C15H26O (222.1983546)


Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1]. Beta-Eudesmol is a natural oxygenated sesquiterpene, activates hTRPA1, with an EC50 of 32.5 μM. Beta-Eudesmol increases appetite through TRPA1[1].

   

Scopoletol

2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy- (9CI)

C10H8O4 (192.0422568)


Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

Zimco

InChI=1\C8H8O3\c1-11-8-4-6(5-9)2-3-7(8)10\h2-5,10H,1H

C8H8O3 (152.0473418)


D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

   

Ferulaldehyde

InChI=1\C10H10O3\c1-13-10-7-8(3-2-6-11)4-5-9(10)12\h2-7,12H,1H3\b3-2

C10H10O3 (178.062991)


Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1]. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1].

   

AI3-12134

InChI=1\C8H8O2\c1-6(9)7-4-2-3-5-8(7)10\h2-5,10H,1H

C8H8O2 (136.0524268)


2'-Hydroxyacetophenone is found in alcoholic beverages. 2'-Hydroxyacetophenone is present in tomato, cassia, fried beef, rum, whiskey, cocoa, coffee and black tea. 2'-Hydroxyacetophenone is a flavouring ingredient. Building block in chemical synthesis. 2'-Hydroxyacetophenone is found in alcoholic beverages. 2'-Hydroxyacetophenone is present in tomato, cassia, fried beef, rum, whiskey, cocoa, coffee and black tea. 2'-Hydroxyacetophenone is a flavouring ingredient. Building block in chemical synthesis.

   

Phytodolor

2H-1- Benzopyran-2-one, 7-hydroxy-6,8-dimethoxy-

C11H10O5 (222.052821)


Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2]. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2].

   

c0276

Acetophenone, 2-hydroxy- (8CI)

C8H8O2 (136.0524268)


2-Hydroxyacetophenone is a principal root volatile of the Carissa edulis[1]. 2-Hydroxyacetophenone shows inhibitory effects on infection of HIV/SARS-CoV S pseudovirus with an IC50 of 1.8 mM[2]. 2-Hydroxyacetophenone is a principal root volatile of the Carissa edulis[1]. 2-Hydroxyacetophenone shows inhibitory effects on infection of HIV/SARS-CoV S pseudovirus with an IC50 of 1.8 mM[2].

   

3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

C20H22O7 (374.1365462)


   

(+)-4-Epi-cryptomeridiol

(+)-4-Epi-cryptomeridiol

C15H28O2 (240.20891880000002)


A natural product found in Citrus hystrix.

   

10-(benzoyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,7,8,8a,10,11,12,12b,13,14b-hexadecahydropicene-4-carbonyl benzoate

10-(benzoyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,7,8,8a,10,11,12,12b,13,14b-hexadecahydropicene-4-carbonyl benzoate

C44H56O5 (664.4127526)


   

(4as,7r,8s)-8-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

(4as,7r,8s)-8-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

C15H24O3 (252.1725354)


   

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C22H22O12 (478.1111212)


   

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

C15H24O2 (236.1776204)


   

(1s,2s,4r,4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(benzoyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,7,8,8a,10,11,12,12b,13,14b-hexadecahydropicene-4-carbonyl benzoate

(1s,2s,4r,4as,6as,6br,8ar,10s,12ar,12br,14bs)-10-(benzoyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,7,8,8a,10,11,12,12b,13,14b-hexadecahydropicene-4-carbonyl benzoate

C44H56O5 (664.4127526)


   

(4as,7r,8r)-8-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

(4as,7r,8r)-8-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

C15H24O3 (252.1725354)


   

(4as,7r)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

(4as,7r)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

C15H22O2 (234.1619712)


   

(4as,7r)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

(4as,7r)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

C15H24O2 (236.1776204)


   

(3e,7s,10r)-7-(2-hydroxypropan-2-yl)-4,10-dimethylcyclodec-3-en-1-one

(3e,7s,10r)-7-(2-hydroxypropan-2-yl)-4,10-dimethylcyclodec-3-en-1-one

C15H26O2 (238.1932696)


   

3-(acetyloxy)-5-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexane-1-carboxylic acid

3-(acetyloxy)-5-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexane-1-carboxylic acid

C18H20O10 (396.105642)


   

(1r,7s,8as)-7-(2-hydroxypropan-2-yl)-1-methyl-3,5,6,7,8,8a-hexahydro-1h-naphthalen-2-one

(1r,7s,8as)-7-(2-hydroxypropan-2-yl)-1-methyl-3,5,6,7,8,8a-hexahydro-1h-naphthalen-2-one

C14H22O2 (222.1619712)


   

(2s,4r)-4-hydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

(2s,4r)-4-hydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

C15H18O2 (230.1306728)


   

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

C15H22O2 (234.1619712)


   

(2r,3r,4r)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolane-2,3-diol

(2r,3r,4r)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolane-2,3-diol

C20H24O7 (376.1521954)


   

2-butoxy-4,6-dimethyloxane-3,4,5-triol

2-butoxy-4,6-dimethyloxane-3,4,5-triol

C11H22O5 (234.14671620000001)


   

(3r,4as,7r)-3-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

(3r,4as,7r)-3-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

C15H24O3 (252.1725354)


   

(2r,3'as,6r,7's,8ar,9'as,9'br)-6,7'-bis(2-hydroxypropan-2-yl)-4,5',8a,9'a-tetramethyl-3'a,5,6,6',7,7',8,8',9',9'b-decahydro-1h-spiro[naphthalene-2,2'-naphtho[1,2-b]furan]-3,3',4'-trione

(2r,3'as,6r,7's,8ar,9'as,9'br)-6,7'-bis(2-hydroxypropan-2-yl)-4,5',8a,9'a-tetramethyl-3'a,5,6,6',7,7',8,8',9',9'b-decahydro-1h-spiro[naphthalene-2,2'-naphtho[1,2-b]furan]-3,3',4'-trione

C31H44O6 (512.3137724000001)


   

(2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,2,4-triol

(2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,2,4-triol

C20H26O7 (378.1678446)


   

1-({1-[2-(2-hydroxypropoxy)propoxy]propan-2-yl}oxy)propan-2-ol

1-({1-[2-(2-hydroxypropoxy)propoxy]propan-2-yl}oxy)propan-2-ol

C12H26O5 (250.17801459999998)


   

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-octahydronaphthalen-1-ol

7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-octahydronaphthalen-1-ol

C15H28O2 (240.20891880000002)


   

6,7'-bis(2-hydroxypropan-2-yl)-4,5',8a,9'a-tetramethyl-3'a,5,6,6',7,7',8,8',9',9'b-decahydro-1h-spiro[naphthalene-2,2'-naphtho[1,2-b]furan]-3,3',4'-trione

6,7'-bis(2-hydroxypropan-2-yl)-4,5',8a,9'a-tetramethyl-3'a,5,6,6',7,7',8,8',9',9'b-decahydro-1h-spiro[naphthalene-2,2'-naphtho[1,2-b]furan]-3,3',4'-trione

C31H44O6 (512.3137724000001)


   

(3r,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-3-ol

(3r,4s,5r)-5-(4-hydroxy-3-methoxyphenyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-(hydroxymethyl)oxolan-3-ol

C20H24O7 (376.1521954)


   

7-(2-hydroxypropan-2-yl)-1-methyl-3,5,6,7,8,8a-hexahydro-1h-naphthalen-2-one

7-(2-hydroxypropan-2-yl)-1-methyl-3,5,6,7,8,8a-hexahydro-1h-naphthalen-2-one

C14H22O2 (222.1619712)


   

4-hydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

4-hydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

C15H18O2 (230.1306728)


   

(4as,7r)-7-(2-hydroxypropan-2-yl)-4a-methyl-5,6,7,8-tetrahydronaphthalen-2-one

(4as,7r)-7-(2-hydroxypropan-2-yl)-4a-methyl-5,6,7,8-tetrahydronaphthalen-2-one

C14H20O2 (220.14632200000003)


   

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C21H20O11 (448.100557)


   

(2s,3s)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,2,4-triol

(2s,3s)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,2,4-triol

C20H26O7 (378.1678446)