apigenin-7-O-beta-D-glucuronide methyl ester

ID: ALA464868

Chembl Id: CHEMBL464868

Cas Number: 53538-13-9

PubChem CID: 13844658

Max Phase: Preclinical

Molecular Formula: C22H20O11

Molecular Weight: 460.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H]1O[C@@H](Oc2cc(O)c3c(=O)cc(-c4ccc(O)cc4)oc3c2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C22H20O11/c1-30-21(29)20-18(27)17(26)19(28)22(33-20)31-11-6-12(24)16-13(25)8-14(32-15(16)7-11)9-2-4-10(23)5-3-9/h2-8,17-20,22-24,26-28H,1H3/t17-,18-,19+,20-,22+/m0/s1

Standard InChI Key:  XXKIWCKZQFBXIR-SXFAUFNYSA-N

Alternative Forms

1. Parent:

   

   ALA464868

   Apigenin 7-O-methylglucuronide

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: 460.39

Molecular Weight (Monoisotopic): 460.1006

AlogP: 0.23

#Rotatable Bonds: 4

Polar Surface Area: 176.12

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.30

CX Basic pKa: ┄

CX LogP: 0.90

CX LogD: 0.54

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: 1.67

References

1. Yoo NH, Jang DS, Yoo JL, Lee YM, Kim YS, Cho JH, Kim JS..  (2008)  Erigeroflavanone, a flavanone derivative from the flowers of Erigeron annuus with protein glycation and aldose reductase inhibitory activity.,  71  (4): [PMID:18298080] [10.1021/np070489a]

2. Sugimoto S, Yamano Y, Desoukey SY, Katakawa K, Wanas AS, Otsuka H, Matsunami K..  (2019)  Isolation of Sesquiterpene-Amino Acid Conjugates, Onopornoids A-D, and a Flavonoid Glucoside from Onopordum alexandrinum.,  82  (6): [PMID:31199638] [10.1021/acs.jnatprod.8b00948]

Source

Source(1):

• Scientific Literature