Protocatechuic acid

3,4-dihydroxybenzoic acid

C7H6O4 (154.0266076)


Protocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, 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. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment. 3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies . 3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as a human xenobiotic metabolite, a plant metabolite, an antineoplastic agent, an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor and an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor. It is a member of catechols and a dihydroxybenzoic acid. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate. 3,4-Dihydroxybenzoic acid is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. Protocatechuic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Vaccinium myrtillus Leaf (part of); Menyanthes trifoliata leaf (part of) ... View More ... A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-50-3 (retrieved 2024-06-29) (CAS RN: 99-50-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

   

Taraxerol

(3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol

C30H50O (426.386145)


Taraxerol is a pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15. It has a role as a metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. Taraxerol is a natural product found in Diospyros morrisiana, Liatris acidota, and other organisms with data available. See also: Myrica cerifera root bark (part of). Constituent of Taraxacum officinale (dandelion). Taraxerol is found in many foods, some of which are kiwi, scarlet bean, prairie turnip, and grapefruit/pummelo hybrid. Taraxerol is found in alcoholic beverages. Taraxerol is a constituent of Taraxacum officinale (dandelion)

   

Lupeol

(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

C30H50O (426.386145)


Lupeol is a pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. It has a role as an anti-inflammatory drug and a plant metabolite. It is a secondary alcohol and a pentacyclic triterpenoid. It derives from a hydride of a lupane. Lupeol has been investigated for the treatment of Acne. Lupeol is a natural product found in Ficus auriculata, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

   

Afzelin

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

C21H20O10 (432.105642)


Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available. [Raw Data] CBA27_Afzelin_neg_30eV_1-1_01_1585.txt [Raw Data] CBA27_Afzelin_pos_20eV_1-1_01_1549.txt [Raw Data] CBA27_Afzelin_pos_10eV_1-1_01_1540.txt [Raw Data] CBA27_Afzelin_neg_10eV_1-1_01_1576.txt [Raw Data] CBA27_Afzelin_neg_20eV_1-1_01_1584.txt [Raw Data] CBA27_Afzelin_neg_40eV_1-1_01_1586.txt [Raw Data] CBA27_Afzelin_pos_30eV_1-1_01_1550.txt [Raw Data] CBA27_Afzelin_pos_50eV_1-1_01_1552.txt [Raw Data] CBA27_Afzelin_pos_40eV_1-1_01_1551.txt [Raw Data] CBA27_Afzelin_neg_50eV_1-1_01_1587.txt Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

   

Afzelin

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

C21H20O10 (432.105642)


5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one can be found in a number of food items such as endive, linden, peach, and ginkgo nuts, which makes 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one a potential biomarker for the consumption of these food products. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

   

Afzelin

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

C21H20O10 (432.105642)


Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available. A glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. Acquisition and generation of the data is financially supported in part by CREST/JST. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

   

Taraxerol

(3S,4aR,6aR,8aR,12aR,12bS,14aR,14bR)-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol

C30H50O (426.386145)


Taraxerol is a pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15. It has a role as a metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. Taraxerol is a natural product found in Diospyros morrisiana, Liatris acidota, and other organisms with data available. See also: Myrica cerifera root bark (part of). A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.

   

Catechol

(+)-Catechin Hydrate

C15H14O6 (290.0790344)


Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

   

3,4-Dihydroxybenzoic acid

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266076)


   
   
   

[(2r,3s,4s,5r,6s)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

[(2r,3s,4s,5r,6s)-6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

C28H24O17 (632.1013454)


   

(3r,4as,6as,6br,8ar,12as,14ar,14bs)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol

(3r,4as,6as,6br,8ar,12as,14ar,14bs)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol

C30H50O (426.386145)


   

(1r,19r,21s,22r,23r)-6,7,8,11,12,13,22-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-23-yl 3,4,5-trihydroxybenzoate

(1r,19r,21s,22r,23r)-6,7,8,11,12,13,22-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-23-yl 3,4,5-trihydroxybenzoate

C34H26O22 (786.0915696)


   

[(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

[(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

C28H24O16 (616.1064304)


   

(1s,2s,5r,8s,11r,13s)-5,12,12-trimethyl-14-oxapentacyclo[11.2.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadec-6-en-13-ol

(1s,2s,5r,8s,11r,13s)-5,12,12-trimethyl-14-oxapentacyclo[11.2.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadec-6-en-13-ol

C20H30O2 (302.224568)


   

12-ethenyl-2,6,6,10,12-pentamethyl-5-oxo-4,11-dioxatricyclo[8.4.0.0²,⁷]tetradecane-3-carboxylic acid

12-ethenyl-2,6,6,10,12-pentamethyl-5-oxo-4,11-dioxatricyclo[8.4.0.0²,⁷]tetradecane-3-carboxylic acid

C20H30O5 (350.209313)


   

(2e)-5-[(1r,4as,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-en-1-ol

(2e)-5-[(1r,4as,5r,8as)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]-3-methylpent-2-en-1-ol

C20H34O2 (306.2558664)


   

(2s,3r,4s,5s,6r)-4,5-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

(2s,3r,4s,5s,6r)-4,5-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

C27H24O18 (636.0962604)


   

(1s,19r,21s,22r,23r)-6,7,8,11,12,13,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-22-yl 3,4,5-trihydroxybenzoate

(1s,19r,21s,22r,23r)-6,7,8,11,12,13,23-heptahydroxy-3,16-dioxo-21-(3,4,5-trihydroxybenzoyloxy)-2,17,20-trioxatetracyclo[17.3.1.0⁴,⁹.0¹⁰,¹⁵]tricosa-4(9),5,7,10,12,14-hexaen-22-yl 3,4,5-trihydroxybenzoate

C34H26O22 (786.0915696)


   

2-[(2r,4as,5r,6s,8as)-2-[(1r)-2-({2-[(2s,4as,5r,6s,8as)-5-(carboxymethyl)-2-ethenyl-2,5,8a-trimethyl-hexahydro-1-benzopyran-6-yl]-2-methylpropanoyl}oxy)-1-hydroxyethyl]-5-(carboxymethyl)-2,5,8a-trimethyl-hexahydro-1-benzopyran-6-yl]-2-methylpropanoic acid

2-[(2r,4as,5r,6s,8as)-2-[(1r)-2-({2-[(2s,4as,5r,6s,8as)-5-(carboxymethyl)-2-ethenyl-2,5,8a-trimethyl-hexahydro-1-benzopyran-6-yl]-2-methylpropanoyl}oxy)-1-hydroxyethyl]-5-(carboxymethyl)-2,5,8a-trimethyl-hexahydro-1-benzopyran-6-yl]-2-methylpropanoic acid

C40H64O11 (720.4448394)


   

(7r,8s,26r,28s,29s)-1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11,13,15,17(22),18,20,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate

(7r,8s,26r,28s,29s)-1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11,13,15,17(22),18,20,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate

C41H28O27 (952.0817938)


   

(3r,4as,6as,8r,10ar,10br)-3,4a,7,7,10a-pentamethyl-3-[(2r)-oxiran-2-yl]-octahydro-1h-naphtho[2,1-b]pyran-8-ol

(3r,4as,6as,8r,10ar,10br)-3,4a,7,7,10a-pentamethyl-3-[(2r)-oxiran-2-yl]-octahydro-1h-naphtho[2,1-b]pyran-8-ol

C20H34O3 (322.25078140000005)


   

(1s,4s,9s,10r,12s,13s)-13-hydroxy-5,5,9,13-tetramethyltetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecan-6-one

(1s,4s,9s,10r,12s,13s)-13-hydroxy-5,5,9,13-tetramethyltetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecan-6-one

C20H32O2 (304.24021719999996)


   

(1r,2r,6s,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

(1r,2r,6s,10s,11r,13s,14r,15r)-13-(acetyloxy)-1-hydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

C30H37NO7 (523.2569892)


   

3-[(1r,4r,5r,6r,8s,9s)-9-(hydroxymethyl)-5-methyl-4-(prop-1-en-2-yl)tricyclo[6.2.2.0¹,⁶]dodecan-5-yl]propanoic acid

3-[(1r,4r,5r,6r,8s,9s)-9-(hydroxymethyl)-5-methyl-4-(prop-1-en-2-yl)tricyclo[6.2.2.0¹,⁶]dodecan-5-yl]propanoic acid

C20H32O3 (320.23513219999995)


   

3-[(4-{[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

3-[(4-{[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

C27H30O15 (594.158463)


   

5,5,9,13-tetramethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-6-ol

5,5,9,13-tetramethyl-15-oxapentacyclo[11.3.1.0¹,¹⁰.0⁴,⁹.0¹⁴,¹⁶]heptadecan-6-ol

C20H32O2 (304.24021719999996)


   

[(2r,4as,5r,6s,8as)-2-ethenyl-6-(1-methoxy-2-methyl-1-oxopropan-2-yl)-2,5,8a-trimethyl-hexahydro-1-benzopyran-5-yl]acetic acid

[(2r,4as,5r,6s,8as)-2-ethenyl-6-(1-methoxy-2-methyl-1-oxopropan-2-yl)-2,5,8a-trimethyl-hexahydro-1-benzopyran-5-yl]acetic acid

C21H34O5 (366.24061140000003)


   

2-[(1s,4s,5s,6r,9r)-5-(carboxymethyl)-5-methyl-10-methylidenetricyclo[7.2.1.0¹,⁶]dodecan-4-yl]-2-methylpropanoic acid

2-[(1s,4s,5s,6r,9r)-5-(carboxymethyl)-5-methyl-10-methylidenetricyclo[7.2.1.0¹,⁶]dodecan-4-yl]-2-methylpropanoic acid

C20H30O4 (334.214398)


   

(1s,2r,4r,5r,8r,9r)-4-[(3r)-3,4-dihydroxy-4-methylpentyl]-4,8-dimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol

(1s,2r,4r,5r,8r,9r)-4-[(3r)-3,4-dihydroxy-4-methylpentyl]-4,8-dimethyltricyclo[6.3.1.0²,⁵]dodecane-1,9-diol

C20H36O4 (340.2613456)


   

(2r,3s)-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

(2r,3s)-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C21H24O12S (500.0988424)


   

(1r,4s,9s,10s,13s)-5,5,9,13-tetramethyl-6-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-7-one

(1r,4s,9s,10s,13s)-5,5,9,13-tetramethyl-6-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-7-one

C19H28O2 (288.2089188)


   

3-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

3-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

C22H22O11 (462.11620619999997)


   

3-[(2r,4ar,5r,6s,8as)-2-ethenyl-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-hexahydro-1-benzopyran-5-yl]propanoic acid

3-[(2r,4ar,5r,6s,8as)-2-ethenyl-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-hexahydro-1-benzopyran-5-yl]propanoic acid

C20H34O4 (338.24569640000004)


   

(2s,3r,4r,5r,6r)-3-hydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

(2s,3r,4r,5r,6r)-3-hydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

C34H28O22 (788.1072188)


   

7-hydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadeca-4,7,14-trien-6-one

7-hydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadeca-4,7,14-trien-6-one

C19H24O2 (284.17762039999997)


   

3-[(1r,4r,5r,6r,8s)-5-methyl-9-methylidene-4-(prop-1-en-2-yl)tricyclo[6.2.2.0¹,⁶]dodecan-5-yl]propanoic acid

3-[(1r,4r,5r,6r,8s)-5-methyl-9-methylidene-4-(prop-1-en-2-yl)tricyclo[6.2.2.0¹,⁶]dodecan-5-yl]propanoic acid

C20H30O2 (302.224568)


   

3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran

3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran

C20H34O (290.2609514)


   

2-[5-(carboxymethyl)-2,5,8a-trimethyl-2-(oxiran-2-yl)-hexahydro-1-benzopyran-6-yl]-2-methylpropanoic acid

2-[5-(carboxymethyl)-2,5,8a-trimethyl-2-(oxiran-2-yl)-hexahydro-1-benzopyran-6-yl]-2-methylpropanoic acid

C20H32O6 (368.2198772)


   

3-[(1s,4r,5r,6r,8s,9r)-9-hydroxy-9-(hydroxymethyl)-5-methyl-4-(prop-1-en-2-yl)tricyclo[6.2.2.0¹,⁶]dodecan-5-yl]propanoic acid

3-[(1s,4r,5r,6r,8s,9r)-9-hydroxy-9-(hydroxymethyl)-5-methyl-4-(prop-1-en-2-yl)tricyclo[6.2.2.0¹,⁶]dodecan-5-yl]propanoic acid

C20H32O4 (336.2300472)


   

3,4a,7,7,10a-pentamethyl-3-(oxiran-2-yl)-octahydronaphtho[2,1-b]pyran-8-one

3,4a,7,7,10a-pentamethyl-3-(oxiran-2-yl)-octahydronaphtho[2,1-b]pyran-8-one

C20H32O3 (320.23513219999995)


   

3-[9-(hydroxymethyl)-5-methyl-4-(prop-1-en-2-yl)tricyclo[6.2.2.0¹,⁶]dodecan-5-yl]propanoic acid

3-[9-(hydroxymethyl)-5-methyl-4-(prop-1-en-2-yl)tricyclo[6.2.2.0¹,⁶]dodecan-5-yl]propanoic acid

C20H32O3 (320.23513219999995)


   

(7ar)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

(7ar)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

C15H24O (220.18270539999997)


   

methyl 2-{4-acetyl-5,9-dimethyl-11-oxatetracyclo[7.3.1.0¹,⁶.0¹⁰,¹²]tridecan-5-yl}acetate

methyl 2-{4-acetyl-5,9-dimethyl-11-oxatetracyclo[7.3.1.0¹,⁶.0¹⁰,¹²]tridecan-5-yl}acetate

C19H28O4 (320.19874880000003)


   

(1s,4s,6r,9s,10r,12s,13s)-5,5,9,13-tetramethyltetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,13-diol

(1s,4s,6r,9s,10r,12s,13s)-5,5,9,13-tetramethyltetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]hexadecane-6,13-diol

C20H34O2 (306.2558664)


   

6-hydroxy-5,5,9,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-7-one

6-hydroxy-5,5,9,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-7-one

C20H30O2 (302.224568)


   

(1s,2r,7s,10s,12r)-12-ethenyl-2,6,6,10,12-pentamethyl-5,11-dioxatricyclo[8.4.0.0²,⁷]tetradecan-4-one

(1s,2r,7s,10s,12r)-12-ethenyl-2,6,6,10,12-pentamethyl-5,11-dioxatricyclo[8.4.0.0²,⁷]tetradecan-4-one

C19H30O3 (306.21948299999997)


   

(3r,4as,6as,10as,10bs)-3-ethenyl-9-hydroxy-3,4a,7,7,10a-pentamethyl-1h,2h,5h,6h,6ah,10bh-naphtho[2,1-b]pyran-8-one

(3r,4as,6as,10as,10bs)-3-ethenyl-9-hydroxy-3,4a,7,7,10a-pentamethyl-1h,2h,5h,6h,6ah,10bh-naphtho[2,1-b]pyran-8-one

C20H30O3 (318.21948299999997)


   

methyl 2-{4-acetyl-5,9-dimethyltricyclo[7.2.1.0¹,⁶]dodec-10-en-5-yl}acetate

methyl 2-{4-acetyl-5,9-dimethyltricyclo[7.2.1.0¹,⁶]dodec-10-en-5-yl}acetate

C19H28O3 (304.2038338)


   

(1r,3ar,5ar,5br,7ar,9r,11ar,11br,13ar,13bs)-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol

(1r,3ar,5ar,5br,7ar,9r,11ar,11br,13ar,13bs)-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol

C30H50O (426.386145)


   

(4as,4br,5r,7r,10ar)-7-ethenyl-5-hydroxy-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one

(4as,4br,5r,7r,10ar)-7-ethenyl-5-hydroxy-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one

C20H30O2 (302.224568)


   

(4r)-4-[(3s)-3-hydroxybutyl]-5,5-dimethyl-3-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-one

(4r)-4-[(3s)-3-hydroxybutyl]-5,5-dimethyl-3-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclohex-2-en-1-one

C19H32O8 (388.20970719999997)


   

(1s,2r,5r,6r,8s,9r,12r,14s)-5,13,13-trimethyl-7,15-dioxahexacyclo[12.2.2.1⁵,⁹.0¹,¹².0²,⁹.0⁶,⁸]nonadecan-14-ol

(1s,2r,5r,6r,8s,9r,12r,14s)-5,13,13-trimethyl-7,15-dioxahexacyclo[12.2.2.1⁵,⁹.0¹,¹².0²,⁹.0⁶,⁸]nonadecan-14-ol

C20H30O3 (318.21948299999997)


   

5-(5-chloro-3,4-dihydroxy-3-methylpentyl)-1,1,4a,6-tetramethyl-4,7,8,8a-tetrahydro-3h-naphthalen-2-one

5-(5-chloro-3,4-dihydroxy-3-methylpentyl)-1,1,4a,6-tetramethyl-4,7,8,8a-tetrahydro-3h-naphthalen-2-one

C20H33ClO3 (356.2118098000001)


   

2-[5-(carboxymethyl)-5-methyl-10-methylidenetricyclo[7.2.1.0¹,⁶]dodecan-4-yl]-2-methylpropanoic acid

2-[5-(carboxymethyl)-5-methyl-10-methylidenetricyclo[7.2.1.0¹,⁶]dodecan-4-yl]-2-methylpropanoic acid

C20H30O4 (334.214398)


   

(3r,4as,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran

(3r,4as,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran

C20H34O (290.2609514)


   

2-[5-(carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid

2-[5-(carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0¹,⁶]dodec-10-en-4-yl]-2-methylpropanoic acid

C20H30O4 (334.214398)


   

10-(acetyloxy)-3-ethenyl-5,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-6-yl acetate

10-(acetyloxy)-3-ethenyl-5,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-hexahydro-2h-naphtho[2,1-b]pyran-6-yl acetate

C24H36O8 (452.2410056)