(4R,4aS)-4,8-Dihydroxy-6-methyl-9-oxo-4,9-dihydro-xanthene-4a-carboxylic acid (2-hydroxy-ethyl)-amide

ID: ALA89464

Chembl Id: CHEMBL89464

PubChem CID: 44322794

Max Phase: Preclinical

Molecular Formula: C17H17NO6

Molecular Weight: 331.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c2c(c1)O[C@@]1(C(=O)NCCO)C(=CC=C[C@H]1O)C2=O

Standard InChI:  InChI=1S/C17H17NO6/c1-9-7-11(20)14-12(8-9)24-17(16(23)18-5-6-19)10(15(14)22)3-2-4-13(17)21/h2-4,7-8,13,19-21H,5-6H2,1H3,(H,18,23)/t13-,17+/m1/s1

Standard InChI Key:  SRLBYYFTPDTTRA-DYVFJYSZSA-N

Alternative Forms

1. Parent:

   

   ALA89464

   (4R,4aS)-4,8-dihydroxy-N-(2-hydroxyethyl)-6-methyl-9-oxo-4H-xanthene-4a-carboxamide

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: 331.32

Molecular Weight (Monoisotopic): 331.1056

AlogP: -0.02

#Rotatable Bonds: 3

Polar Surface Area: 116.09

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: ┄

CX LogP: 0.64

CX LogD: 0.62

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: 1.61

References

1. Sato S, Suga Y, Yoshimura T, Nakagawa R, Tsuji T, Umemura K, Andoh T..  (1999)  Syntheses of novel antitumor dihydroxanthone derivatives with inhibitory activity against DNA topoisomerase II.,  9  (18): [PMID:10509910] [10.1016/s0960-894x(99)00440-0]

Source

Source(1):

• Scientific Literature