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: ALA3350557

Chembl Id: CHEMBL3350557

PubChem CID: 10323743

Max Phase: Preclinical

Molecular Formula: C27H23N3O7

Molecular Weight: 501.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1[C@H](O)[C@@H](O)[C@H](n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)C(=O)NC4=O)O[C@@H]1CO

Standard InChI:  InChI=1S/C27H23N3O7/c1-36-24-15(10-31)37-27(23(33)22(24)32)30-14-9-5-3-7-12(14)17-19-18(25(34)29-26(19)35)16-11-6-2-4-8-13(11)28-20(16)21(17)30/h2-9,15,22-24,27-28,31-33H,10H2,1H3,(H,29,34,35)/t15-,22-,23-,24-,27-/m1/s1

Standard InChI Key:  JNMXCWUKDUQJFF-HHJYCPGKSA-N

Alternative Forms

1. Parent:

   

   ALA3350557

   12-(4-O-methyl-beta-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[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: 501.50

Molecular Weight (Monoisotopic): 501.1536

AlogP: 1.94

#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: 1.38

CX LogD: 1.29

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.24

Np Likeness Score: 1.02

References

1. Moreau P, Anizon F, Sancelme M, Prudhomme M, Bailly C, Carrasco C, Ollier M, Sevère D, Riou JF, Fabbro D, Meyer T, Aubertin AM..  (1998)  Syntheses and biological evaluation of indolocarbazoles, analogues of rebeccamycin, modified at the imide heterocycle.,  41  (10): [PMID:9572888] [10.1021/jm970843+]

2. 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]

3. Anizon F, Belin L, Moreau P, Sancelme M, Voldoire A, Prudhomme M, Ollier M, Sevère D, Riou JF, Bailly C, Fabbro D, Meyer T..  (1997)  Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group.,  40  (21): [PMID:9341921] [10.1021/jm9702084]

4. Pereira ER, Belin L, Sancelme M, Prudhomme M, Ollier M, Rapp M, Sevère D, Riou JF, Fabbro D, Meyer T..  (1996)  Structure-activity relationships in a series of substituted indolocarbazoles: topoisomerase I and protein kinase C inhibition and antitumoral and antimicrobial properties.,  39  (22): [PMID:8893841] [10.1021/jm9603779]

5. Moreau P, Anizon F, Sancelme M, Prudhomme M, Bailly C, Sevère D, Riou JF, Fabbro D, Meyer T, Aubertin AM..  (1999)  Syntheses and biological activities of rebeccamycin analogues. Introduction of a halogenoacetyl substituent.,  42  (4): [PMID:10052965] [10.1021/jm980396d]

Source

Source(1):

• Scientific Literature