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Isoferulic acid

PubChem CID: 736186

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Compound Synonyms Isoferulic acid, 3-Hydroxy-4-methoxycinnamic acid, 537-73-5, 25522-33-2, Hesperetic acid, trans-Isoferulic acid, 3-(3-Hydroxy-4-methoxyphenyl)acrylic acid, (E)-3-(3-hydroxy-4-methoxyphenyl)acrylic acid, (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid, 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-, Cinnamic acid, 3-hydroxy-4-methoxy-, Isoferulate, 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid, UNII-XSQ2K2G7MC, (E)-3'-Hydroxy-4'-methoxycinnamic acid, XSQ2K2G7MC, 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, CHEBI:27794, (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid, EINECS 208-676-0, NSC 51987, NSC-51987, trans-3-Hydroxy-4-methoxycinnamic acid, BRN 2212760, 4-O-METHYLCAFFEIC ACID, CHEMBL233295, 4-10-00-01777 (Beilstein Handbook Reference), (E)-3-(3-hydroxy-4-methoxy-phenyl)-acrylic acid, 3-Hydroxy-4-methoxycinnamic acid (isoferulic acid), (2E)-3-(3-HYDROXY-4-METHOXYPHENYL)ACRYLIC ACID, cis-Isoferulic acid, 3-Hydroxy-4-methoxycinnamate, 3-hydroxy-4-methoxy-cinnamic acid, Hesperetate, Isoferulasaure, DTXSID501009309, rans-3-(3-Hydroxy-4-methoxyphenyl)acrylic acid, trans-3-Hydroxy-4-methoxycinnamic acid, Hesperetic acid, trans-Isoferulic acid, EINECS 247-071-6, MFCD00004391, Isoferulic Acid ,(S), bmse000618, MLS000563054, SCHEMBL249041, SCHEMBL249042, 3-hydroxy-4-methoxy-Cinnamate, 3-Hydroxy-4-methoxycinnamic acid, predominantly trans, GTPL7980, HY-N0761A, 3-Hydroxy-4-methoxycinnamic-acid, DTXCID90908460, 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)-, (2E)-, DTXSID901314847, HMS2268G06, ABA52233, HY-N0761, NSC51987, STR05122, BBL036268, BDBM50241245, s3764, STL186177, AKOS000141174, CCG-266533, CS-W020120, DB07109, FH24260, NCGC00247490-01, NCGC00247490-02, 1ST40364, AC-34927, LS-13768, MS-11465, SMR001215828, trans-Isoferulic acid, analytical standard, 3-(3-hydroxy-4-methoxyphenyl)-2-Propenoate, H0524, NS00014666, EN300-50983, (E)-3-(3-hydroxy-4-methoxyphenyl)acrylicacid, EN300-331979, G77265, ISOFERULIC ACID (CONSTITUENT OF BLACK COHOSH), Q27096447, Z2693271860, (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid #, 3-Hydroxy-4-methoxycinnamic acid, predominantly trans, 97%, ISOFERULIC ACID (CONSTITUENT OF BLACK COHOSH) [DSC], 208-676-0, 4FE
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 66.8
Hydrogen Bond Donor Count 2.0
Pfizer 3 75 Rule False
Scaffold Graph Level C1CCCCC1
Np Classifier Class Cinnamic acids and derivatives
Deep Smiles COcccccc6O)))/C=C/C=O)O
Heavy Atom Count 14.0
Classyfire Class Cinnamic acids and derivatives
Description It is used as a food additive, listed in the EAFUS Food Additive Database (Jan 2001) Isoferulic acid is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids, such as caffeic, ferulic, and {rho}-coumaric, with quinic acid. CGA are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2 - 9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation. (PMID: 17884997). Isoferulic acid is found in many foods, some of which are sunflower, peanut, common wheat, and vinegar.
Scaffold Graph Node Level C1CCCCC1
Classyfire Subclass Hydroxycinnamic acids and derivatives
Isotope Atom Count 0.0
Molecular Complexity 224.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id O42713, n.a., Q12794, Q96QE3, P83916, P03372, P63092, Q9NUW8
Iupac Name (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
Prediction Hob 1.0
Class Cinnamic acids and derivatives
Veber Rule True
Classyfire Superclass Phenylpropanoids and polyketides
Xlogp 1.5
Superclass Phenylpropanoids and polyketides
Subclass Hydroxycinnamic acids and derivatives
Gsk 4 400 Rule True
Molecular Formula C10H10O4
Scaffold Graph Node Bond Level c1ccccc1
Prediction Swissadme 0.0
Inchi Key QURCVMIEKCOAJU-HWKANZROSA-N
Silicos It Class Soluble
Fcsp3 0.1
Logs -2.656
Rotatable Bond Count 3.0
State Solid
Logd 1.299
Synonyms (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoate, 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, 9CI, 3-Hydroxy-4-methoxy-cinnamate, 3-Hydroxy-4-methoxy-cinnamic acid, 3-Hydroxy-4-methoxycinnamate, 3-Hydroxy-4-methoxycinnamic acid, Hesperetate, Hesperetic acid, Hesperetinic acid, Isoferulate, Isoferulic acid, (e)-3-Hydroxy-4-methoxycinnamic acid, (e)-4-Methoxycaffeic acid, (e)-4-O-Methylcaffeic acid, (e)-Hesperetic acid, (e)-Isoferulic acid, 4-Methoxycaffeic acid, 4-O-Methylcaffeic acid, trans-3-Hydroxy-4-methoxycinnamic acid, trans-4-Methoxycaffeic acid, trans-4-O-Methylcaffeic acid, trans-Hesperetic acid, trans-Isoferulic acid, (2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoate, 3'-Hydroxy-4'-methoxycinnamic acid, (e)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, (2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acid, 2-hydroxy-4-methoxy-trans-cinnamic-acid, isoferulate, isoferulic acid
Substituent Name Hydroxycinnamic acid, Coumaric acid or derivatives, Cinnamic acid, Methoxyphenol, Phenylpropene, Methoxybenzene, Styrene, Phenol ether, Anisole, Phenol, Alkyl aryl ether, Benzenoid, Monocyclic benzene moiety, Monocarboxylic acid or derivatives, Ether, Carboxylic acid, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aromatic homomonocyclic compound
Esol Class Soluble
Functional Groups c/C=C/C(=O)O, cO, cOC
Compound Name Isoferulic acid
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 194.058
Formal Charge 0.0
Monoisotopic Mass 194.058
Hydrogen Bond Acceptor Count 4.0
Molecular Weight 194.18
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 0.0
Total Bond Stereocenter Count 1.0
Molecular Framework Aromatic homomonocyclic compounds
Lipinski Rule Of 5 True
Esol -2.114396057142857
Inchi InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
Smiles COC1=C(C=C(C=C1)/C=C/C(=O)O)O
Nring 1.0
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 1.0
Egan Rule True
Taxonomy Direct Parent Hydroxycinnamic acids
Np Classifier Superclass Phenylpropanoids (C6-C3)

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