beta-D-ribopyranose tetrakis(3,4,5-trihydroxybenzoate)

ID: ALA383459

Chembl Id: CHEMBL383459

PubChem CID: 11600236

Max Phase: Preclinical

Molecular Formula: C33H26O21

Molecular Weight: 758.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@@H]1OC[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H]1OC(=O)c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1

Standard InChI:  InChI=1S/C33H26O21/c34-14-1-10(2-15(35)23(14)42)29(46)51-22-9-50-33(54-32(49)13-7-20(40)26(45)21(41)8-13)28(53-31(48)12-5-18(38)25(44)19(39)6-12)27(22)52-30(47)11-3-16(36)24(43)17(37)4-11/h1-8,22,27-28,33-45H,9H2/t22-,27-,28-,33+/m1/s1

Standard InChI Key:  XQNFOUUSFRMWPI-CPSNIHODSA-N

Alternative Forms

1. Parent:

   

   ALA383459

   [(3R,4R,5R,6S)-4,5,6-tris[(3,4,5-trihydroxybenzoyl)oxy]oxan-3-yl] 3,4,5-trihydroxybenzoate

Molecule Features

Natural Product: No

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: 758.55

Molecular Weight (Monoisotopic): 758.0967

AlogP: 1.34

#Rotatable Bonds: 8

Polar Surface Area: 357.19

Molecular Species: NEUTRAL

HBA: 21

HBD: 12

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.55

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 3.74

Aromatic Rings: 4

Heavy Atoms: 54

QED Weighted: 0.07

Np Likeness Score: 0.66

References

1. Ren Y, Himmeldirk K, Chen X..  (2006)  Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues.,  49  (9): [PMID:16640344] [10.1021/jm060087k]

2. G-Doyagüez E, Carrero P, Madrona A, Rodriguez-Salamanca P, Martínez-Gualda B, Camarasa MJ, Jimeno ML, Bennallack PR, Finnell JG, Tsang TM, Christensen KA, San-Félix A, Rogers MS..  (2019)  Galloyl Carbohydrates with Antiangiogenic Activity Mediated by Capillary Morphogenesis Gene 2 (CMG2) Protein Binding.,  62  (8): [PMID:30964669] [10.1021/acs.jmedchem.8b01988]

Source

Source(1):

• Scientific Literature