3,9-dibromo-12-(3,4-dihydroxy-6-hydroxymethyl-5-methoxytetrahydro-2H-2-pyranyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione

ID: ALA51826

Chembl Id: CHEMBL51826

PubChem CID: 473005

Max Phase: Preclinical

Molecular Formula: C27H21Br2N3O7

Molecular Weight: 659.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1C(CO)OC(n2c3ccc(Br)cc3c3c4c(c5c6cc(Br)ccc6[nH]c5c32)C(=O)NC4=O)C(O)C1O

Standard InChI:  InChI=1S/C27H21Br2N3O7/c1-38-24-15(8-33)39-27(23(35)22(24)34)32-14-5-3-10(29)7-12(14)17-19-18(25(36)31-26(19)37)16-11-6-9(28)2-4-13(11)30-20(16)21(17)32/h2-7,15,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)

Standard InChI Key:  VJBOQMQRYVPKIL-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA51826

   12-[3,4-Dihydroxy-6-(hydroxymethyl)-5-methoxyperhydro-2H-pyran-2-yl]-3,9-dibromoindolo[2,3-a]3-pyrrolino[3,4-c]carbazole-5,7-dione

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: 659.29

Molecular Weight (Monoisotopic): 656.9746

AlogP: 3.46

#Rotatable Bonds: 3

Polar Surface Area: 146.04

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.03

CX Basic pKa: ┄

CX LogP: 2.92

CX LogD: 2.83

Aromatic Rings: 5

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: 0.90

References

1. Moreau P, Anizon F, Sancelme M, Prudhomme M, Sevère D, Riou JF, Goossens JF, Hénichart JP, Bailly C, Labourier E, Tazzi J, Fabbro D, Meyer T, Aubertin AM..  (1999)  Synthesis, mode of action, and biological activities of rebeccamycin bromo derivatives.,  42  (10): [PMID:10346933] [10.1021/jm980702n]

Source

Source(1):

• Scientific Literature