Vanicoside B

ID: ALA492323

Chembl Id: CHEMBL492323

Cas Number: 155179-21-8

PubChem CID: 10033855

Max Phase: Preclinical

Molecular Formula: C49H48O20

Molecular Weight: 956.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)OC[C@H]2O[C@H](O[C@]3(COC(=O)/C=C/c4ccc(O)cc4)O[C@H](COC(=O)/C=C/c4ccc(O)cc4)[C@@H](O)[C@@H]3OC(=O)/C=C/c3ccc(O)cc3)[C@H](O)[C@@H](O)[C@@H]2O)ccc1O

Standard InChI:  InChI=1S/C49H48O20/c1-62-36-24-31(8-19-35(36)53)12-22-40(55)63-25-37-43(58)45(60)46(61)48(66-37)69-49(27-65-41(56)21-10-29-4-15-33(51)16-5-29)47(67-42(57)23-11-30-6-17-34(52)18-7-30)44(59)38(68-49)26-64-39(54)20-9-28-2-13-32(50)14-3-28/h2-24,37-38,43-48,50-53,58-61H,25-27H2,1H3/b20-9+,21-10+,22-12+,23-11+/t37-,38-,43-,44-,45+,46-,47+,48-,49+/m1/s1

Standard InChI Key:  ALSDWGAQQGXOHC-PWYSLETCSA-N

Alternative Forms

1. Parent:

   

   ALA492323

   VANICOSIDE B

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: 956.90

Molecular Weight (Monoisotopic): 956.2739

AlogP: 2.49

#Rotatable Bonds: 18

Polar Surface Area: 303.96

Molecular Species: NEUTRAL

HBA: 20

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.87

CX Basic pKa: ┄

CX LogP: 6.23

CX LogD: 6.22

Aromatic Rings: 4

Heavy Atoms: 69

QED Weighted: 0.04

Np Likeness Score: 1.01

References

1. Zimmermann ML, Sneden AT..  (1994)  Vanicosides A and B, protein kinase C inhibitors from Polygonum pensylvanicum.,  57  (2): [PMID:8176400] [10.1021/np50104a007]

2. Takasaki M, Kuroki S, Kozuka M, Konoshima T..  (2001)  New phenylpropanoid esters of sucrose from Polygonum lapathifolium.,  64  (10): [PMID:11678656] [10.1021/np010222q]

3. Kim D, Wang CY, Hu R, Lee JY, Luu TT, Park HJ, Lee SK..  (2019)  Antitumor Activity of Vanicoside B Isolated from Persicaria dissitiflora by Targeting CDK8 in Triple-Negative Breast Cancer Cells.,  82  (11): [PMID:31622095] [10.1021/acs.jnatprod.9b00720]

Source

Source(1):

• Scientific Literature