3,4,5-Trihydroxy-benzoic acid (2S,3S)-5,7-dihydroxy-2-(3,4,5-trihydroxy-phenyl)-chroman-3-yl ester

ID: ALA338988

Chembl Id: CHEMBL338988

Cas Number: 188819-08-1

PubChem CID: 2824823

Max Phase: Preclinical

Molecular Formula: C22H18O11

Molecular Weight: 458.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1

Standard InChI:  InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m0/s1

Standard InChI Key:  WMBWREPUVVBILR-RXVVDRJESA-N

Alternative Forms

1. Parent:

   

   ALA338988

   cis-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate

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: 458.38

Molecular Weight (Monoisotopic): 458.0849

AlogP: 2.23

#Rotatable Bonds: 3

Polar Surface Area: 197.37

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.99

CX Basic pKa: ┄

CX LogP: 3.08

CX LogD: 2.97

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.21

Np Likeness Score: 1.65

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. Tedaldi L, Wagner GK.  (2014)  Beyond substrate analogues: new inhibitor chemotypes for glycosyltransferases,  5  (8): [10.1039/C4MD00086B]

Source

Source(1):

• Scientific Literature