5-O-beta-D-glucopyranosyl-7-methoxy-3',4'-dihydroxy-4-phenylcoumarin

ID: ALA463401

Chembl Id: CHEMBL463401

Cas Number: 116310-58-8

PubChem CID: 13962183

Max Phase: Preclinical

Molecular Formula: C22H22O11

Molecular Weight: 462.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2c(-c3ccc(O)c(O)c3)cc(=O)oc2c1

Standard InChI:  InChI=1S/C22H22O11/c1-30-10-5-14-18(11(7-17(26)31-14)9-2-3-12(24)13(25)4-9)15(6-10)32-22-21(29)20(28)19(27)16(8-23)33-22/h2-7,16,19-25,27-29H,8H2,1H3/t16-,19-,20+,21-,22-/m1/s1

Standard InChI Key:  JZBHUVGJBWDUSA-RECXWPGBSA-N

Alternative Forms

1. Parent:

   

   ALA463401

   4-(3,4-Dihydroxyphenyl)-5-beta-D-glucopyranosyloxy-7-methoxycoumarin

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: 462.41

Molecular Weight (Monoisotopic): 462.1162

AlogP: 0.06

#Rotatable Bonds: 5

Polar Surface Area: 179.28

Molecular Species: NEUTRAL

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.06

CX Basic pKa:

CX LogP: -0.12

CX LogD: -0.13

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.22

Np Likeness Score: 1.65

References

1. Argotte-Ramos R, Ramírez-Avila G, Rodríguez-Gutiérrez Mdel C, Ovilla-Muñoz M, Lanz-Mendoza H, Rodríguez MH, Gonzalez-Cortazar M, Alvarez L..  (2006)  Antimalarial 4-phenylcoumarins from the stem bark of Hintonia latiflora.,  69  (10): [PMID:17067158] [10.1021/np060233p]

2. Mata R, Calzada F, Garcia MR..  (1988)  Chemical studies on mexican plants used in traditional medicine, VI. Additional new 4-phenylcoumarins from Exostema caribaeum.,  51  (5): [PMID:3204377] [10.1021/np50059a006]

3. Gonçalves GA, Spillere AR, das Neves GM, Kagami LP, von Poser GL, Canto RFS, Eifler-Lima V..  (2020)  Natural and synthetic coumarins as antileishmanial agents: A review.,  203  [PMID:32668302] [10.1016/j.ejmech.2020.112514]

Source

Source(1):

• Scientific Literature