2,10-Dihydroxy-6-[(pyrazin-2-ylmethyl)amino]-13-(beta-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione

ID: ALA506902

Chembl Id: CHEMBL506902

PubChem CID: 44565944

Max Phase: Preclinical

Molecular Formula: C31H26N6O10

Molecular Weight: 642.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2c(c3c4ccc(O)cc4n(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c3c3[nH]c4cc(O)ccc4c23)C(=O)N1NCc1cnccn1

Standard InChI:  InChI=1S/C31H26N6O10/c38-11-19-26(41)27(42)28(43)31(46-19)47-37-18-8-14(40)2-4-16(18)21-23-22(20-15-3-1-13(39)7-17(15)35-24(20)25(21)37)29(44)36(30(23)45)34-10-12-9-32-5-6-33-12/h1-9,19,26-28,31,34-35,38-43H,10-11H2/t19-,26-,27+,28-,31+/m1/s1

Standard InChI Key:  ZKTWDOVLQKYFQC-ZYOMLLCTSA-N

Alternative Forms

1. Parent:

   

   ALA506902

   6,20-dihydroxy-13-(pyrazin-2-ylmethylamino)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-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: 642.58

Molecular Weight (Monoisotopic): 642.1710

AlogP: 0.16

#Rotatable Bonds: 6

Polar Surface Area: 235.75

Molecular Species: NEUTRAL

HBA: 14

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.75

CX Basic pKa: 1.78

CX LogP: -1.09

CX LogD: -1.11

Aromatic Rings: 6

Heavy Atoms: 47

QED Weighted: 0.11

Np Likeness Score: 0.54

References

1. Sunami S, Nishimura T, Nishimura I, Ito S, Arakawa H, Ohkubo M..  (2009)  Synthesis and biological activities of topoisomerase I inhibitors, 6-arylmethylamino analogues of edotecarin.,  52  (10): [PMID:19397324] [10.1021/jm801641t]

Source

Source(1):

• Scientific Literature