(2S,3S)-2-(3,4-Dihydroxy-phenyl)-chroman-3,5,7-triol

ID: ALA129482

Chembl Id: CHEMBL129482

Cas Number: 35323-91-2

PubChem CID: 182232

Max Phase: Phase

Molecular Formula: C15H14O6

Molecular Weight: 290.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-epicatechin | Epicatechin | (+)-Epicatechin|35323-91-2|ent-Epicatechin|d-Epicatechin|(2S,3S)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol|(+)-epicatechol|Epicatechin, (+)-|(2S,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol|LD6B6TT8Q5|CHEMBL129482|CHEBI:76125|(2S,3S)-3,3',4',5,7-pentahydroxyflavan|cis-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol|(2S,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol|2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydroShow More⌵

Canonical SMILES:  Oc1cc(O)c2c(c1)O[C@@H](c1ccc(O)c(O)c1)[C@@H](O)C2

Standard InChI:  InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m0/s1

Standard InChI Key:  PFTAWBLQPZVEMU-ZFWWWQNUSA-N

Alternative Forms

1. Parent:

   

   ALA129482

   (+)-EPICATECHIN

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 290.27

Molecular Weight (Monoisotopic): 290.0790

AlogP: 1.55

#Rotatable Bonds: 1

Polar Surface Area: 110.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.00

CX Basic pKa:

CX LogP: 1.80

CX LogD: 1.78

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 2.30

References

1. Jeon SY, Bae K, Seong YH, Song KS..  (2003)  Green tea catechins as a BACE1 (beta-secretase) inhibitor.,  13  (22): [PMID:14592472] [10.1016/j.bmcl.2003.09.018]

2. Jeon SY, Bae K, Seong YH, Song KS..  (2003)  Green tea catechins as a BACE1 (beta-secretase) inhibitor.,  13  (22): [PMID:14592472] [10.1016/j.bmcl.2003.09.018]

3. Tasdemir D, Lack G, Brun R, Rüedi P, Scapozza L, Perozzo R..  (2006)  Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids.,  49  (11): [PMID:16722653] [10.1021/jm0600545]

4. Katavic PL, Lamb K, Navarro H, Prisinzano TE..  (2007)  Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships.,  70  (8): [PMID:17685652] [10.1021/np070194x]

5. Deng JZ, Newman DJ, Hecht SM..  (2000)  Use of COMPARE analysis to discover functional analogues of bleomycin.,  63  (9): [PMID:11000034] [10.1021/np000084p]

6. Szewczuk LM, Penning TM..  (2004)  Mechanism-based inactivation of COX-1 by red wine m-hydroquinones: a structure-activity relationship study.,  67  (11): [PMID:15568761] [10.1021/np0498410]

7. Liu AL, Wang HD, Lee SM, Wang YT, Du GH..  (2008)  Structure-activity relationship of flavonoids as influenza virus neuraminidase inhibitors and their in vitro anti-viral activities.,  16  (15): [PMID:18640042] [10.1016/j.bmc.2008.06.049]

8. Jiang HZ, Quan XF, Tian WX, Hu JM, Wang PC, Huang SZ, Cheng ZQ, Liang WJ, Zhou J, Ma XF, Zhao YX..  (2010)  Fatty acid synthase inhibitors of phenolic constituents isolated from Garcinia mangostana.,  20  (20): [PMID:20817450] [10.1016/j.bmcl.2010.08.061]

9. Aoudia H, Ntalli N, Aissani N, Yahiaoui-Zaidi R, Caboni P..  (2012)  Nematotoxic phenolic compounds from Melia azedarach against Meloidogyne incognita.,  60  (47): [PMID:23136941] [10.1021/jf3038874]

10. Rastija V, Medic-Saric M.  (2009)  QSAR modeling of anthocyanins, anthocyanidins and catechins as inhibitors of lipid peroxidation using three-dimensional descriptors,  18  (7): [10.1007/s00044-008-9151-y]

11. Bais HP, Walker TS, Kennan AJ, Stermitz FR, Vivanco JM..  (2003)  Structure-dependent phytotoxicity of catechins and other flavonoids: flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots.,  51  (4): [PMID:12568546] [10.1021/jf020978a]

12. Kim T, Choi HJ, Eom SH, Lee J, Kim TH..  (2014)  Potential α-glucosidase inhibitors from thermal transformation of (+)-catechin.,  24  (6): [PMID:24491460] [10.1016/j.bmcl.2014.01.027]

13. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates