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

ID: ALA507686

PubChem CID: 44565953

Max Phase: Preclinical

Molecular Formula: C33H28N4O11

Molecular Weight: 656.60

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)N1NCc1ccc(O)cc1

Standard InChI:  InChI=1S/C33H28N4O11/c38-12-21-28(42)29(43)30(44)33(47-21)48-37-20-10-16(41)6-8-18(20)23-25-24(22-17-7-5-15(40)9-19(17)35-26(22)27(23)37)31(45)36(32(25)46)34-11-13-1-3-14(39)4-2-13/h1-10,21,28-30,33-35,38-44H,11-12H2/t21-,28-,29+,30-,33+/m1/s1

Standard InChI Key:  JADCIOKDDGPIRK-OJSVXGLKSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA507686

   6,20-dihydroxy-13-[(4-hydroxyphenyl)methylamino]-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: 656.60

Molecular Weight (Monoisotopic): 656.1755

AlogP: 1.08

#Rotatable Bonds: 6

Polar Surface Area: 230.20

Molecular Species: NEUTRAL

HBA: 13

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.68

CX Basic pKa: 2.80

CX LogP: 0.96

CX LogD: 0.94

Aromatic Rings: 6

Heavy Atoms: 48

QED Weighted: 0.11

Np Likeness Score: 0.75

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