epi-catechin-(4beta->8, 2beta->O->7)-afzelechin

ID: ALA499587

Chembl Id: CHEMBL499587

PubChem CID: 44566353

Max Phase: Preclinical

Molecular Formula: C30H24O11

Molecular Weight: 560.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Geranin B | GERANIN B|CHEMBL499587|BDBM50428819

Canonical SMILES:  Oc1ccc([C@H]2Oc3c(c(O)cc4c3[C@H]3c5c(O)cc(O)cc5O[C@@](c5ccc(O)c(O)c5)(O4)[C@@H]3O)C[C@@H]2O)cc1

Standard InChI:  InChI=1S/C30H24O11/c31-14-4-1-12(2-5-14)27-21(37)10-16-18(34)11-23-25(28(16)39-27)26-24-20(36)8-15(32)9-22(24)40-30(41-23,29(26)38)13-3-6-17(33)19(35)7-13/h1-9,11,21,26-27,29,31-38H,10H2/t21-,26+,27+,29+,30-/m0/s1

Standard InChI Key:  GVKLXAPXNKDQGB-TXZJYACMSA-N

Alternative Forms

1. Parent:

   

   ALA499587

   GERANIN B

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: 560.51

Molecular Weight (Monoisotopic): 560.1319

AlogP: 3.09

#Rotatable Bonds: 2

Polar Surface Area: 189.53

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.72

CX Basic pKa: ┄

CX LogP: 3.89

CX LogD: 3.87

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.17

Np Likeness Score: 2.20

References

1. Calzada F, Cerda-García-Rojas CM, Meckes M, Cedillo-Rivera R, Bye R, Mata R..  (1999)  Geranins A and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum.,  62  (5): [PMID:10346950] [10.1021/np980467b]

2. Ramirez-Galicia G, Martinez-Pacheco H, Garduno-Juarez R, Deeb O.  (2012)  Exploring QSAR of antiamoebic agents of isolated natural products by MLR, ANN, and RTO,  21  (9): [10.1007/s00044-011-9767-1]

3. Pesca MS, Dal Piaz F, Sanogo R, Vassallo A, Bruzual de Abreu M, Rapisarda A, Germanò MP, Certo G, De Falco S, De Tommasi N, Braca A..  (2013)  Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities.,  76  (1): [PMID:23268742] [10.1021/np300614u]

Source

Source(1):

• Scientific Literature