NCBI Taxonomy: 13809

Anthocerotophyta (ncbi_taxid: 13809)

found 26 associated metabolites at clade taxonomy rank level.

Ancestor: Embryophyta

Child Taxonomies: Anthocerotopsida, Leiosporocerotopsida

Caffeic acid

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C9H8O4 (180.0423)


Caffeic acid is a hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. It has a role as a plant metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxycinnamic acid and a member of catechols. Caffeic Acid is a natural product found in Pavetta indica, Eupatorium cannabinum, and other organisms with data available. Caffeic Acid is an orally bioavailable, hydroxycinnamic acid derivative and polyphenol, with potential anti-oxidant, anti-inflammatory, and antineoplastic activities. Upon administration, caffeic acid acts as an antioxidant and prevents oxidative stress, thereby preventing DNA damage induced by free radicals. Caffeic acid targets and inhibits the histone demethylase (HDM) oncoprotein gene amplified in squamous cell carcinoma 1 (GASC1; JMJD2C; KDM4C) and inhibits cancer cell proliferation. GASC1, a member of the KDM4 subgroup of Jumonji (Jmj) domain-containing proteins, demethylates trimethylated lysine 9 and lysine 36 on histone H3 (H3K9 and H3K36), and plays a key role in tumor cell development. Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Arctium lappa Root (part of); Comfrey Leaf (part of) ... View More ... 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. Caffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925). Caffeic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=331-39-5 (retrieved 2024-06-28) (CAS RN: 331-39-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

methyl 16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-22-(3-oxo-3-{[(2e)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaene-3-carboxylate

methyl 16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-22-(3-oxo-3-{[(2e)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaene-3-carboxylate

C55H74N4O5 (870.5659)


   

methyl 16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

methyl 16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

C55H74N4O5 (870.5659)


   

(2s)-2-{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}pentanedioic acid

(2s)-2-{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}pentanedioic acid

C13H15NO7 (297.0848)


   

methyl (3r,21s,22s)-16-ethenyl-11-ethyl-12-formyl-17,21,26-trimethyl-4-oxo-22-(3-oxo-3-{[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

methyl (3r,21s,22s)-16-ethenyl-11-ethyl-12-formyl-17,21,26-trimethyl-4-oxo-22-(3-oxo-3-{[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

C55H72N4O6 (884.5452)


   

2-[(4-hydroxyphenyl)formamido]pentanedioic acid

2-[(4-hydroxyphenyl)formamido]pentanedioic acid

C12H13NO6 (267.0743)


   

methyl (21s,22s)-16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

methyl (21s,22s)-16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

C55H74N4O5 (870.5659)


   

o-phosphoethanolamine; bis(nonane)

o-phosphoethanolamine; bis(nonane)

C20H48NO4P (397.3321)


   

(2r)-2-{[(3,4-dihydroxyphenyl)(hydroxy)methylidene]amino}pentanedioic acid

(2r)-2-{[(3,4-dihydroxyphenyl)(hydroxy)methylidene]amino}pentanedioic acid

C12H13NO7 (283.0692)


   

(2s)-2-{[(2e)-1-hydroxy-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

(2s)-2-{[(2e)-1-hydroxy-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

C15H17NO7 (323.1005)


   

2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

C14H15NO6 (293.0899)


   

(2r,3r,4z)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid

(2r,3r,4z)-3-(3,4-dihydroxyphenyl)-4-[(4-hydroxyphenyl)methylidene]-5-oxooxolane-2-carboxylic acid

C18H14O7 (342.0739)


   

methyl (3r,12z,21s,22s)-16-ethenyl-11-ethyl-12-(hydroxymethylidene)-17,21,26-trimethyl-4-oxo-22-(3-oxo-3-{[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,5(26),6,8,10,13(25),14,16,18(24),19-decaene-3-carboxylate

methyl (3r,12z,21s,22s)-16-ethenyl-11-ethyl-12-(hydroxymethylidene)-17,21,26-trimethyl-4-oxo-22-(3-oxo-3-{[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,5(26),6,8,10,13(25),14,16,18(24),19-decaene-3-carboxylate

C55H72N4O6 (884.5452)


   

(2r)-2-{[(2z)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

(2r)-2-{[(2z)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

C14H15NO6 (293.0899)


   

(2r)-2-[(4-hydroxyphenyl)formamido]pentanedioic acid

(2r)-2-[(4-hydroxyphenyl)formamido]pentanedioic acid

C12H13NO6 (267.0743)


   

(1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl hexadecanoate

(1r,3as,3bs,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl hexadecanoate

C45H80O2 (652.6158)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)


   

(2z)-3-[(3,4-dihydroxyphenyl)methyl]-4-hydroxy-6,7-dihydro-1h-1,5-benzodiazonine-6-carboxylic acid

(2z)-3-[(3,4-dihydroxyphenyl)methyl]-4-hydroxy-6,7-dihydro-1h-1,5-benzodiazonine-6-carboxylic acid

C19H18N2O5 (354.1216)


   

2-{[(3,4-dihydroxyphenyl)(hydroxy)methylidene]amino}pentanedioic acid

2-{[(3,4-dihydroxyphenyl)(hydroxy)methylidene]amino}pentanedioic acid

C12H13NO7 (283.0692)


   

(2s)-2-{[(2z)-1-hydroxy-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

(2s)-2-{[(2z)-1-hydroxy-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

C15H17NO7 (323.1005)


   

2-{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}pentanedioic acid

2-{[hydroxy(4-hydroxy-3-methoxyphenyl)methylidene]amino}pentanedioic acid

C13H15NO7 (297.0848)


   

(2z,6r)-3-[(3,4-dihydroxyphenyl)methyl]-4-hydroxy-6,7-dihydro-1h-1,5-benzodiazonine-6-carboxylic acid

(2z,6r)-3-[(3,4-dihydroxyphenyl)methyl]-4-hydroxy-6,7-dihydro-1h-1,5-benzodiazonine-6-carboxylic acid

C19H18N2O5 (354.1216)


   

(1r,2s,3s,4r)-3-{[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)cyclobutane-1-carboxylic acid

(1r,2s,3s,4r)-3-{[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)cyclobutane-1-carboxylic acid

C27H24O11 (524.1319)


   

2-{[1-hydroxy-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

2-{[1-hydroxy-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-ylidene]amino}pentanedioic acid

C15H17NO7 (323.1005)


   

3-[(3,4-dihydroxyphenyl)methyl]-4-hydroxy-6,7-dihydro-1h-1,5-benzodiazonine-6-carboxylic acid

3-[(3,4-dihydroxyphenyl)methyl]-4-hydroxy-6,7-dihydro-1h-1,5-benzodiazonine-6-carboxylic acid

C19H18N2O5 (354.1216)


   

methyl (3r,21s,22s)-16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

methyl (3r,21s,22s)-16-ethenyl-11-ethyl-12,17,21,26-tetramethyl-4-oxo-22-(3-oxo-3-{[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

C55H74N4O5 (870.5659)