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Luteic acid

PubChem CID: 5319108

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Compound Synonyms Luteic acid, Luteolic acid, B54CJS6VNV, 476-67-5, UNII-B54CJS6VNV, 6H-Dibenzo(b,d)pyran-1-carboxylic acid, 3,4,8,9,10-pentahydroxy-6-oxo-, DTXSID90197216, 3,4,8,9,10-Pentahydroxy-6-oxo-6H-dibenzo(b,d)pyran-1-carboxylic acid, Luteate, 3,4,8,9,10-Pentahydroxy-6-oxo-6H-benzo(c)chromene-1-carboxylate, 3,4,8,9,10-Pentahydroxy-6-oxo-6H-benzo[c]chromene-1-carboxylate, 3,4,8,9,10-Pentahydroxy-6-oxo-6H-dibenzo[b,d]pyran-1-carboxylic acid, SCHEMBL13637035, DTXCID00119707, Q15088017
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 165.0
Hydrogen Bond Donor Count 6.0
Pfizer 3 75 Rule True
Scaffold Graph Level CC1CC2CCCCC2C2CCCCC12
Np Classifier Class Gallotannins
Deep Smiles Occcc=O)occc6cc%10O))O)))cccc6O))O)))C=O)O
Heavy Atom Count 23.0
Classyfire Class Tannins
Description Luteic acid, also known as luteate, is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Luteic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Luteic acid can be found in guava, which makes luteic acid a potential biomarker for the consumption of this food product. Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula and is an intermediary compound in the synthesis of ellagic acid. It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin .
Scaffold Graph Node Level OC1OC2CCCCC2C2CCCCC12
Classyfire Subclass Hydrolyzable tannins
Isotope Atom Count 0.0
Molecular Complexity 508.0
Database Name cmaup_ingredients;fooddb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Iupac Name 3,4,8,9,10-pentahydroxy-6-oxobenzo[c]chromene-1-carboxylic acid
Prediction Hob 0.0
Veber Rule False
Classyfire Superclass Phenylpropanoids and polyketides
Xlogp 0.8
Gsk 4 400 Rule True
Molecular Formula C14H8O9
Scaffold Graph Node Bond Level O=c1oc2ccccc2c2ccccc12
Prediction Swissadme 0.0
Inchi Key FLZGFQFYDGHWLR-UHFFFAOYSA-N
Silicos It Class Soluble
Fcsp3 0.0
Logs -3.048
Rotatable Bond Count 1.0
Logd 0.618
Synonyms luteic acid
Esol Class Soluble
Functional Groups c=O, cC(=O)O, cO, coc
Compound Name Luteic acid
Prediction Hob Swissadme 0.0
Exact Mass 320.017
Formal Charge 0.0
Monoisotopic Mass 320.017
Hydrogen Bond Acceptor Count 9.0
Molecular Weight 320.21
Gi Absorption False
Covalent Unit Count 1.0
Total Atom Stereocenter Count 0.0
Total Bond Stereocenter Count 0.0
Lipinski Rule Of 5 True
Esol -2.9972809826086957
Inchi InChI=1S/C14H8O9/c15-5-2-4-7(11(19)9(5)17)8-3(13(20)21)1-6(16)10(18)12(8)23-14(4)22/h1-2,15-19H,(H,20,21)
Smiles C1=C2C(=C(C(=C1O)O)O)C3=C(C(=C(C=C3C(=O)O)O)O)OC2=O
Nring 3.0
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 0.0
Egan Rule False
Np Classifier Superclass Phenolic acids (C6-C1)

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