NCBI Taxonomy: 158429

4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in A√ßa√≠ oil, obtained from the fruit of the a√ßa√≠ palm (Euterpe oleracea), at relatively high concetrations (892¬±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843). Isolated from many plants, free and combined. Alkyl esters of 4-hydroxybenzoic acid (see below) are used as food and cosmetic preservatives, mainly in their Na salt form, which makes them more water soluble. They are active at low concentrations and more pH-independent than the commonly used Benzoic acid DVN38-Z and 2,4-Hexadienoic acid GMZ10-P. The taste is more detectable than for those preservatives. Effectiveness increases with chain length of the alcohol, but for some microorganisms this reduces cell permeability and thus counteracts the increased efficiency. 4-Hydroxybenzoic acid is found in many foods, some of which are chicory, corn, rye, and black huckleberry. 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate. 4-Hydroxybenzoic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). See also: Vaccinium myrtillus Leaf (part of); Galium aparine whole (part of); Menyanthes trifoliata leaf (part of) ... View More ... A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. 4-Hydroxybenzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-96-7 (retrieved 2024-07-01) (CAS RN: 99-96-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

Isorhamnetin

4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-

3,4,5,7-tetrahydroxy-3-methoxyflavone is a tetrahydroxyflavone having the 4-hydroxy groups located at the 3- 4- 5- and 7-positions as well as a methoxy group at the 2-position. It has a role as a metabolite and an antimicrobial agent. It is a tetrahydroxyflavone and a monomethoxyflavone. It is functionally related to a quercetin. It is a conjugate acid of a 3,4,5-trihydroxy-3-methoxyflavon-7-olate. 3-O-Methylquercetin is a natural product found in Lotus ucrainicus, Wollastonia biflora, and other organisms with data available. See also: Tobacco Leaf (part of). 3-O-Methylquercetin (3-MQ), a main constituent of Rhamnus nakaharai, inhibits total cAMP and cGMP-phosphodiesterase (PDE) of guinea pig trachealis. 3-O-Methylquercetin (3-MQ) exhibits IC50 values ranging from 1.6-86.9 μM for PDE isozymes (PDE1-5)[1]. 3-O-Methylquercetin (3-MQ), a main constituent of Rhamnus nakaharai, inhibits total cAMP and cGMP-phosphodiesterase (PDE) of guinea pig trachealis. 3-O-Methylquercetin (3-MQ) exhibits IC50 values ranging from 1.6-86.9 μM for PDE isozymes (PDE1-5)[1].

Isorhamnetin

4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-

Isorhamnetin is the methylated metabolite of quercetin. Quercetin is an important dietary flavonoid with in vitro antioxidant activity. However, it is found in human plasma as conjugates with glucuronic acid, sulfate or methyl groups, with no significant amounts of free quercetin present. Isorhamnetin prevents endothelial cell injuries from oxidized LDL via inhibition of lectin-like ox-LDL receptor-1 upregulation, interference of ox-LDL-mediated intracellular signaling pathway (p38MAPK activation, NF-kappaB nuclear translocation, eNOS expression) and the antioxidant activity of isorhamnetin. Isorhamnetin prevents endothelial dysfunction, superoxide production, and overexpression of p47phox induced by angiotensin II. Isorhamnetin appears to be a potent drug against esophageal cancer due to its in vitro potential to not only inhibit proliferation but also induce apoptosis of Eca-109 cells. (PMID: 15493462, 17368593, 17374653, 16963021). Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3 is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It is functionally related to a quercetin. It is a conjugate acid of an isorhamnetin(1-). Isorhamnetin is a natural product found in Lotus ucrainicus, Strychnos pseudoquina, and other organisms with data available. Isorhamnetin is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Peumus boldus leaf (part of). Widespread flavonol found especially in bee pollen, chives, corn poppy leaves, garden cress, fennel, hartwort, red onions, pears, dillweed, parsley and tarragon. Isorhamnetin is found in many foods, some of which are italian sweet red pepper, carrot, yellow wax bean, and lemon balm. A monomethoxyflavone that is quercetin in which the hydroxy group at position 3 is replaced by a methoxy group. Acquisition and generation of the data is financially supported in part by CREST/JST. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K.

3,4-Dihydroxybenzaldehyde

protocatechualdehyde, formyl-14C-labeled

Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus . 3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia). D006401 - Hematologic Agents > D000925 - Anticoagulants Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

ANTHRACENE

Anthracene, sodium salt, ion (1-)

C14H10 (178.078246)

Anthracene, also known as anthrazen or anthracene, sodium salt, ion (1-), is a member of the class of compounds known as anthracenes. Anthracenes are organic compounds containing a system of three linearly fused benzene rings. Anthracene can be found in sorrel, which makes anthracene a potential biomarker for the consumption of this food product. Anthracene is formally rated as an unfounded non-carcinogenic (IARC 3) potentially toxic compound. Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet radiation . PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system (L10) (T3DB).

Blestriarene B

1-(2,7-dihydroxy-4-methoxy-9,10-dihydrophenanthren-1-yl)-4-methoxy-phenanthrene-2,7-diol

C30H24O6 (480.1572804)

Orchinol

2,4-Dimethoxy-7-hydroxy-9,10-dihydrophenanthrene

C16H16O3 (256.10993859999996)

Cinnamic acid

cinnamic acid, 14C-labeled cpd (E)-isomer

C9H8O2 (148.0524268)

Cinnamic acid, also known as (Z)-cinnamate or 3-phenyl-acrylate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Cinnamic acid can be obtained from oil of cinnamon, or from balsams such as storax. Cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Cinnamic acid exists in all living organisms, ranging from bacteria to plants to humans. Outside of the human body, cinnamic acid has been detected, but not quantified in, chinese cinnamons. In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. CONFIDENCE standard compound; INTERNAL_ID 191; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3778; ORIGINAL_PRECURSOR_SCAN_NO 3776 CONFIDENCE standard compound; INTERNAL_ID 191; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3783; ORIGINAL_PRECURSOR_SCAN_NO 3781 Cinnamic acid is a white crystalline hydroxycinnamic acid, which is slightly soluble in water. It is obtained from oil of cinnamon, or from balsams such as storax. cis-Cinnamic acid is found in chinese cinnamon. CONFIDENCE standard compound; INTERNAL_ID 183 Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells. Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells. trans-Cinnamic acid is a natural antimicrobial, with minimal inhibitory concentration (MIC) of 250 μg/mL against fish pathogen A. sobria, SY-AS1[1]. trans-Cinnamic acid is a natural antimicrobial, with minimal inhibitory concentration (MIC) of 250 μg/mL against fish pathogen A. sobria, SY-AS1[1].

Kaempferol 7-O-glucoside

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

C21H20O11 (448.100557)

Gastrodin

2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol

C13H18O7 (286.10524780000003)

Kaempferol 7-glucoside

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

C21H20O11 (448.100557)

Kaempferol 7-glucoside is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Kaempferol 7-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 7-glucoside can be found in a number of food items such as flaxseed, ginkgo nuts, white cabbage, and saffron, which makes kaempferol 7-glucoside a potential biomarker for the consumption of these food products.

3,4-Dihydroxybenzaldehyde

3,4-Dihydroxybenzaldehyde, Vetec(TM) reagent grade, 97\\%

Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus . 3,4-dihydroxybenzaldehyde is a dihydroxybenzaldehyde. Also known as protocatechuic aldehyde, protocatechualdehyde is a naturally-occuring phenolic aldehyde that is found in barley, green cavendish bananas, grapevine leaves and root of the herb S. miltiorrhiza. Protocatechualdehyde possesses antiproliferative and pro-apoptotic properties against human breast cancer cells and colorectal cancer cells by reducing the expression of pro-oncogenes β-catenin and cyclin D1. 3,4-Dihydroxybenzaldehyde is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. See also: Black Cohosh (part of). 3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia). D006401 - Hematologic Agents > D000925 - Anticoagulants Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

Shanciol

trans- (-) -3,4,5,6-Tetrahydro-2- (4-hydroxy-3-methoxyphenyl) -11-methoxy-2H-phenanthro [ 2,1-b ] pyran-3,8-diol

Nudol

2,7-dihydroxy-3,4-dimethoxyphenanthrene

C16H14O4 (270.0892044)

2,7-Phenanthrenediol, 3,4-dimethoxy- is a natural product found in Pinalia spicata, Bulbophyllum vaginatum, and other organisms with data available.

8-C-p-Hydroxybenzylkaempferol

3,5,7,4-Tetrahydroxy-8- (4-hydroxyphenylmethyl) flavone

C22H16O7 (392.0895986)

physcion

9,10-Anthracenedione, 1,8-dihydroxy-3-methoxy-6-methyl- (9CI)

C16H12O5 (284.0684702)

Physcion, also known as emodin monomethyl ether or parienin, is a member of the class of compounds known as anthraquinones. Anthraquinones are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Physcion is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Physcion can be synthesized from 2-methylanthraquinone. Physcion can also be synthesized into torososide B and physcion 8-gentiobioside. Physcion can be found in common sage, garden rhubarb, and sorrel, which makes physcion a potential biomarker for the consumption of these food products. Physcion has also been shown to protect lichens against UV-B light, at high altitudes in Alpine regions. The UV-B light stimulates production of parietin and the parietin protects the lichens from damage. Lichens in arctic regions such as Svarlbard retain this capability though they do not encounter damaging levels of UV-B, a capability that could help protect the lichens in case of Ozone layer thinning .

6-methoxykaempferol

3,5,7-Trihydroxy-2- (4-hydroxyphenyl) -6-methoxy-4H-1-benzopyran-4-one

Isorhamnetin

4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)- (9CI)

Glucoside present in the leaves of Peumus boldus (boldo). Isorhamnetin 3-dirhamnoside is found in fruits. Annotation level-1 Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K.

Cinnamic Acid

trans-cinnamic acid

C9H8O2 (148.0524268)

Trans-cinnamic acid, also known as (2e)-3-phenyl-2-propenoic acid or (E)-cinnamate, is a member of the class of compounds known as cinnamic acids. Cinnamic acids are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Trans-cinnamic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Trans-cinnamic acid is a sweet, balsam, and honey tasting compound and can be found in a number of food items such as maitake, mustard spinach, common wheat, and barley, which makes trans-cinnamic acid a potential biomarker for the consumption of these food products. Trans-cinnamic acid can be found primarily in saliva. Trans-cinnamic acid exists in all living species, ranging from bacteria to humans. Trans-cinnamic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cinnamic acid is an organic compound with the formula C6H5CHCHCO2H. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common . Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells. Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells. trans-Cinnamic acid is a natural antimicrobial, with minimal inhibitory concentration (MIC) of 250 μg/mL against fish pathogen A. sobria, SY-AS1[1]. trans-Cinnamic acid is a natural antimicrobial, with minimal inhibitory concentration (MIC) of 250 μg/mL against fish pathogen A. sobria, SY-AS1[1].

2,4-bis[(4-hydroxyphenyl)methyl]-5-methoxy-3-(2-phenylethyl)phenol

C29H28O4 (440.19874880000003)

2,3,4,7-tetramethoxyphenanthrene

C18H18O4 (298.1205028)

2,4,7-trimethoxy-9,10-dihydrophenanthrene

C17H18O3 (270.1255878)

1-[(4-Hydroxyphenyl)methyl]-4-methoxyphenanthrene-2,7-diol

C22H18O4 (346.1205028)

4-methoxy-9,10-dihydrophenanthrene-1,2,7-triol

C15H14O4 (258.0892044)

2,4,7-trimethoxyphenanthrene

C17H16O3 (268.10993859999996)

4-hydroxybenzoate

4-Hydroxybenzoic acid

4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

protocatechuic aldehyde

3,4-dihydroxybenzaldehyde

Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

3-[2-(3-hydroxyphenyl)ethyl]-5-methoxyphenol

NCGC00385266-01!3-[2-(3-hydroxyphenyl)ethyl]-5-methoxyphenol

C15H16O3 (244.1099386)

7-methoxy-9,10-dihydrophenanthrene-2,5-diol

NCGC00385352-01!7-methoxy-9,10-dihydrophenanthrene-2,5-diol

kaempferol 7-O-glucoside

kaempferol 7-O-β-D-glucopyranoside

C21H20O11 (448.100557)

p-Hydroxybenzaldehyde

C7H6O2 (122.0367776)

p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

p-Hydroxybenzoic acid

4-Hydroxybenzaldehyde

C7H6O2 (122.0367776)

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266076)

4-methoxy-9,10-dihydrophenanthrene-2,7-diol

3,4-dihydroxybenzaldehyde

56684-87-8

3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenol

C16H18O3 (258.1255878)

3'-O-Methylbatatasin III shows spasmolytic activity[1]. 3'-O-Methylbatatasin III shows spasmolytic activity[1].

ANTHRACENE

C14H10 (178.078246)

Dibenzyl

1,2-dihydrostilbene

C14H14 (182.1095444)

(3s,4s)-3-(4-hydroxy-3-methoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4,8-diol

2-oxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaene-6,13-diol

C15H12O3 (240.0786402)

1,5,7-trimethoxyphenanthrene-2,6-diol

C17H16O5 (300.0997686)

(1s,3r,6s,8s,11r,12s,15r,16r)-15-[(2r,5s)-5-ethyl-6-methylhept-6-en-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C32H54O (454.41744339999997)

3-[2-(3-hydroxyphenyl)ethyl]-4-[(4-hydroxyphenyl)methyl]-5-methoxyphenol

C22H22O4 (350.1518012)

12,16-dimethyl-15-(5,5,6-trimethylhept-6-en-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-one

C30H48O (424.37049579999996)

3-[2-(3-hydroxyphenyl)ethenyl]-5-methoxyphenol

2-(hydroxymethyl)-6-[(4-methoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenanthren-2-yl)oxy]oxane-3,4,5-triol

C27H32O13 (564.1842822)

[7-hydroxy-2-(3-hydroxy-5-methoxyphenyl)-10-methoxy-2h,3h,4h,5h-phenanthro[2,1-b]furan-3-yl]methyl acetate

(2s,3r,4r,5r,6r)-2-(7-hydroxy-4-methoxy-9,10-dihydrophenanthren-2-yl)-6-(hydroxymethyl)oxane-3,4,5-triol

C21H24O7 (388.1521954)

3-[2-(3-hydroxyphenyl)ethyl]-2,4,6-tris[(4-hydroxyphenyl)methyl]-5-methoxyphenol

C36H34O6 (562.2355264)

2-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-3,8-diol

3-hydroxy-5-methyl-3-{[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}hexanoic acid

C21H30O11 (458.178803)

[3-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-1-methoxy-5h,6h,9h,10h-phenanthro[2,3-b]furan-10-yl]methyl acetate

(3r,4s)-3-(4-hydroxy-3-methoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4,8-diol

7-methoxy-1-[(4-methoxyphenyl)methyl]-9,10-dihydrophenanthrene-2,4-diol

C23H22O4 (362.1518012)

(1s,3r,6s,7s,8s,11r,12s,15r,16r)-15-[(2r,5r)-5-ethyl-5,6-dimethylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl (2z)-3-(4-hydroxyphenyl)prop-2-enoate

C41H60O3 (600.454221)

1,8-bis[(4-hydroxyphenyl)methyl]-4-methoxyphenanthrene-2,7-diol

C29H24O5 (452.1623654)

8'-[(4-hydroxyphenyl)methyl]-4,5'-dimethoxy-9h,9'h,10h,10'h-[1,3'-biphenanthrene]-2,2',7,7'-tetrol

C37H32O7 (588.2147921999999)

1-[(4-hydroxyphenyl)methyl]-4,8-dimethoxyphenanthrene-2,7-diol

C23H20O5 (376.13106700000003)

2',7-dimethoxy-9h,9'h,10h,10'h-[1,1'-biphenanthrene]-2,4,4',7'-tetrol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenoxy}oxane-3,4,5-triol

C22H28O8 (420.1784088)

8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methoxy-3,4,10,11-tetrahydro-2h-1-oxatetraphen-4-yl acetate

1,2-dihydrophenanthrene

C14H12 (180.0938952)

8'-[(4-hydroxyphenyl)methyl]-4,5'-dimethoxy-9',10'-dihydro-[1,3'-biphenanthrene]-2,2',7,7'-tetrol

C37H30O7 (586.199143)

(1r)-5,7'-dihydroxy-10'-methoxy-2,3-dihydrospiro[indene-1,3'-phenanthro[2,1-b]furan]-2'-one

C25H18O5 (398.1154178)

4,4'-dimethoxy-9h,9'h,10h,10'h-[1,3'-biphenanthrene]-2,2',7,7'-tetrol

15-(5-ethyl-5,6-dimethylhept-6-en-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl 3-(4-hydroxyphenyl)prop-2-enoate

C41H60O3 (600.454221)

(1s,3r,6s,8s,11r,12s,15r,16r)-15-[(2r,5s)-5-ethyl-6-methylhept-6-en-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C41H60O3 (600.454221)

6,13-dihydroxy-5-methoxy-2-oxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-3-one

C16H12O5 (284.0684702)

(3-{[(2s,3r,4r,5s,6r)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxy-3-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}phenyl)chromen-7-ylidene)[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[1-hydroxy-3-(4-oxocyclohexa-2,5-dien-1-ylidene)prop-1-en-1-yl]oxy}methyl)oxan-2-yl]oxidanium

(3-{[(2s,3r,4r,5s,6r)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxy-3-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}phenyl)chromen-7-ylidene)[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[1-hydroxy-3-(4-oxocyclohexa-2,5-dien-1-ylidene)prop-1-en-1-yl]oxy}methyl)oxan-2-yl]oxidanium

[C75H81O40]+ (1621.4303926)

1,1'-biphenanthrene

C28H18 (354.1408428)

(2s,3r,4s,5r,6r)-2-{4-[(2,7-dihydroxy-4-methoxy-9,10-dihydrophenanthren-1-yl)methyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C28H30O9 (510.18897300000003)

1-[(7-hydroxy-5-methoxy-9,10-dihydrophenanthren-2-yl)oxy]-4-methoxyphenanthrene-2,7-diol

C30H24O6 (480.1572804)

4,4'-dimethoxy-9,10-dihydro-[1,1'-biphenanthrene]-2,2',7,7',8,8'-hexol

C30H24O8 (512.1471104)

4-[(4-hydroxyphenyl)methyl]-3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenol

C23H24O4 (364.1674504)

6,13-dihydroxy-2-oxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-3-one

C15H10O4 (254.057906)

4-methoxyphenanthrene-2,7-diol

C15H12O3 (240.0786402)

[(9r,10s)-3-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-1-methoxy-5h,6h,9h,10h-phenanthro[2,3-b]furan-10-yl]methyl acetate

(3r,4r)-8-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-3,4,10,11-tetrahydro-2h-1-oxatetraphen-4-yl acetate

2-(4-hydroxy-3-methoxyphenyl)-4-methoxytricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-6,13-diol

C23H22O5 (378.1467162)

3-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2,4-bis[(4-hydroxyphenyl)methyl]-5-methoxyphenol

C30H30O6 (486.204228)

2-[(7-hydroxy-4-methoxyphenanthren-2-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C21H22O8 (402.1314612)

(3s,4r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-6-methoxy-3,4,10,11-tetrahydro-2h-1-oxatetraphene-4,8-diol

1,3,6-tris[(4-hydroxyphenyl)methyl]-4-methoxy-9,10-dihydrophenanthrene-2,7-diol

C36H32O6 (560.2198771999999)

1-[(5-hydroxy-7-methoxy-9,10-dihydrophenanthren-2-yl)oxy]-4-methoxy-9,10-dihydrophenanthrene-2,7-diol

1-benzylphenanthrene

C21H16 (268.1251936)

[7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-10-methoxy-2h,3h,4h,5h-phenanthro[2,1-b]furan-3-yl]methyl acetate

1,3-dimethoxy-5-[2-(3-methoxyphenyl)ethyl]benzene

C17H20O3 (272.14123700000005)

2,5-dihydroxy-6,7-dimethoxyphenanthrene-4-carboxylic acid

C17H14O6 (314.0790344)

(3s,4s)-8-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate

8-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate

2-(4-hydroxy-3-methoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-3,8-diol

2,4-bis[(4-hydroxyphenyl)methyl]-5-methoxy-3-[2-(3-methoxyphenyl)ethyl]phenol

C30H30O5 (470.209313)

(2s,3r)-2-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-3,8-diol

(3r,4r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4,8-diol

5-[2-(3-hydroxyphenyl)ethyl]-2,4-bis[(4-hydroxyphenyl)methyl]-3-methoxyphenol

C29H28O5 (456.1936638)

2-hydroxy-4-methyl-2-{2-oxo-2-[(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]ethyl}pentanoic acid

C21H30O11 (458.178803)

5-methoxy-2-oxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-6,13-diol

C16H14O4 (270.0892044)

[3-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-1-methoxy-5h,6h,9h,10h-phenanthro[2,3-b]furan-10-yl]methyl acetate

4,4',8,8'-tetramethoxy-[1,1'-biphenanthrene]-2,2',7,7'-tetrol

C32H26O8 (538.1627596000001)

(3r,4s)-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4,8-diol

[(2r,3s)-7-hydroxy-2-(3-hydroxy-5-methoxyphenyl)-10-methoxy-2h,3h,4h,5h-phenanthro[2,1-b]furan-3-yl]methyl acetate

6-methoxy-2-oxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-13-ol

C16H14O3 (254.0942894)

2-(hydroxymethyl)-6-{3-[2-(3-hydroxyphenyl)ethyl]-5-methoxyphenoxy}oxane-3,4,5-triol

C21H26O8 (406.1627596)

4,7-dimethoxy-9,10-dihydrophenanthrene-2,6-diol

C16H16O4 (272.1048536)

(3s,4r)-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-3,4,10,11-tetrahydro-2h-1-oxatetraphene-4,8-diol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{3-[2-(3-hydroxyphenyl)ethyl]-5-methoxyphenoxy}oxane-3,4,5-triol

C21H26O8 (406.1627596)

{4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate

C24H28O9 (460.17332380000005)

1,3-dimethoxy-5-(2-phenylethyl)benzene

C16H18O2 (242.1306728)

hexacosyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C36H62O4 (558.4647851999999)

3-[(4-hydroxyphenyl)methyl]-4-methoxy-9,10-dihydrophenanthrene-2,7-diol

C22H20O4 (348.13615200000004)

4,6-bis[(4-hydroxyphenyl)methyl]-5-(2-phenylethyl)benzene-1,3-diol

C28H26O4 (426.18309960000005)

3',4,5',7-tetramethoxy-9',10'-dihydro-[1,2'-biphenanthrene]-2,7'-diol

C32H28O6 (508.1885788)

5-[2-(4-hydroxyphenyl)ethyl]-4,6-bis[(4-hydroxyphenyl)methyl]benzene-1,3-diol

C28H26O5 (442.17801460000004)

2-hydroxy-7-methoxyphenanthrene-1,4-dione

C15H10O4 (254.057906)

(3r,4s)-8-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-3,4,10,11-tetrahydro-2h-1-oxatetraphen-4-yl acetate

2,4,6-tris[(4-hydroxyphenyl)methyl]-3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenol

C37H36O6 (576.2511756)

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(4-methoxy-7-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenanthren-2-yl)oxy]oxane-3,4,5-triol

C27H32O13 (564.1842822)

7-{2-hydroxy-4-[2-(3-hydroxyphenyl)ethyl]-6-methoxyphenoxy}-2-methoxy-9,10-dihydrophenanthren-4-ol

C30H28O6 (484.1885788)

(2r)-2-hydroxy-4-methyl-2-{2-oxo-2-[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]ethyl}pentanoic acid

C21H30O11 (458.178803)

4,4'-dimethoxy-9h,9'h,10h,10'h-[1,1'-biphenanthrene]-2,2',7,7'-tetrol

[(9r,10s)-3-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-1-methoxy-5h,6h,9h,10h-phenanthro[2,3-b]furan-10-yl]methyl acetate

[(2r,3s)-7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-10-methoxy-2h,3h,4h,5h-phenanthro[2,1-b]furan-3-yl]methyl acetate

5,13-dihydroxy-6,7-dimethoxy-2-oxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),9,11(15),12-heptaen-3-one

C17H12O6 (312.06338519999997)

3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4,8-diol

(3ar)-3a,9-dihydroxy-7,10-dimethoxy-4,5-dihydropyren-1-one

C18H16O5 (312.0997686)

(3r,4r)-3-[(3r,4r)-6-hydroxy-4-methoxy-3,4-dihydro-2h-1-benzopyran-3-yl]-4-methoxy-3,4-dihydro-2h-1-benzopyran-6-ol

C20H22O6 (358.1416312)

4-[(4-hydroxyphenyl)methyl]-5-(2-phenylethyl)benzene-1,3-diol

C21H20O3 (320.14123700000005)

3-[(1e)-2-(3-hydroxyphenyl)ethenyl]-5-methoxyphenol

(2r,3s)-2-(4-hydroxy-3-methoxyphenyl)-5-[2-(3-hydroxyphenyl)ethyl]-7-methoxy-3,4-dihydro-2h-1-benzopyran-3-ol

C25H26O6 (422.17292960000003)

3-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol

C16H18O4 (274.1205028)

3-[2-(3-hydroxyphenyl)ethyl]-2-[(4-hydroxyphenyl)methyl]-5-methoxyphenol

C22H22O4 (350.1518012)

(2r)-2-(4-hydroxy-3-methoxyphenyl)-4-methoxytricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-6,13-diol

C23H22O5 (378.1467162)

1,4-bis[(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl] (2r)-2-(2-methylpropyl)-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanedioate

C40H56O22 (888.3263076000001)

8-[(4-hydroxyphenyl)methyl]-9,10-dihydrophenanthrene-2,5-diol

C21H18O3 (318.12558779999995)

2-(hydroxymethyl)-6-{3-methoxy-5-[2-(3-methoxyphenyl)ethyl]phenoxy}oxane-3,4,5-triol

C22H28O8 (420.1784088)

(r)-[(3s,4r)-4-[(s)-(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl](4-hydroxy-3-methoxyphenyl)methyl acetate

C24H28O9 (460.17332380000005)

(3r,4r)-8-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-11-methoxy-2h,3h,4h,5h,6h-phenanthro[2,1-b]pyran-4-yl acetate