2-(5,7-dioxo-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-12-yl)-4-hydroxy-6-hydroxymethyl-5-methoxytetrahydro-2H-3-pyranyl 2-bromoacetate

ID: ALA347684

Chembl Id: CHEMBL347684

PubChem CID: 44370463

Max Phase: Preclinical

Molecular Formula: C29H24BrN3O8

Molecular Weight: 622.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1C(CO)OC(n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)C(=O)NC4=O)C(OC(=O)CBr)C1O

Standard InChI:  InChI=1S/C29H24BrN3O8/c1-39-25-16(11-34)40-29(26(24(25)36)41-17(35)10-30)33-15-9-5-3-7-13(15)19-21-20(27(37)32-28(21)38)18-12-6-2-4-8-14(12)31-22(18)23(19)33/h2-9,16,24-26,29,31,34,36H,10-11H2,1H3,(H,32,37,38)

Standard InChI Key:  XAXUMCRVNQGORJ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA347684

   [2-(12,14-Dioxo-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaen-3-yl)-4-hydroxy-6-(hydroxymethyl)-5-methoxyoxan-3-yl] 2-bromoacetate

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: 622.43

Molecular Weight (Monoisotopic): 621.0747

AlogP: 2.88

#Rotatable Bonds: 5

Polar Surface Area: 152.11

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.03

CX Basic pKa: ┄

CX LogP: 2.55

CX LogD: 2.46

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.13

Np Likeness Score: 0.97

References

1. 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