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

ID: ALA455328

Chembl Id: CHEMBL455328

PubChem CID: 44565943

Max Phase: Preclinical

Molecular Formula: C32H27N5O10

Molecular Weight: 641.59

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)N1NCc1ccncc1

Standard InChI:  InChI=1S/C32H27N5O10/c38-12-20-27(41)28(42)29(43)32(46-20)47-37-19-10-15(40)2-4-17(19)22-24-23(21-16-3-1-14(39)9-18(16)35-25(21)26(22)37)30(44)36(31(24)45)34-11-13-5-7-33-8-6-13/h1-10,20,27-29,32,34-35,38-43H,11-12H2/t20-,27-,28+,29-,32+/m1/s1

Standard InChI Key:  XEZUYMNGNKRDNI-NLOMZQFXSA-N

Alternative Forms

1. Parent:

   

   ALA455328

   6,20-dihydroxy-13-(pyridin-4-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: 641.59

Molecular Weight (Monoisotopic): 641.1758

AlogP: 0.76

#Rotatable Bonds: 6

Polar Surface Area: 222.86

Molecular Species: NEUTRAL

HBA: 13

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.75

CX Basic pKa: 3.47

CX LogP: 0.05

CX LogD: 0.03

Aromatic Rings: 6

Heavy Atoms: 47

QED Weighted: 0.12

Np Likeness Score: 0.66

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