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

ID: ALA448760

PubChem CID: 44565964

Max Phase: Preclinical

Molecular Formula: C33H29N5O11

Molecular Weight: 671.62

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(CO)nc1

Standard InChI:  InChI=1S/C33H29N5O11/c39-11-14-2-1-13(9-34-14)10-35-37-31(46)24-22-17-5-3-15(41)7-19(17)36-26(22)27-23(25(24)32(37)47)18-6-4-16(42)8-20(18)38(27)49-33-30(45)29(44)28(43)21(12-40)48-33/h1-9,21,28-30,33,35-36,39-45H,10-12H2/t21-,28-,29+,30-,33+/m1/s1

Standard InChI Key:  JKIFRESPTATQIO-OJSVXGLKSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA448760

   6,20-dihydroxy-13-[[6-(hydroxymethyl)pyridin-3-yl]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: 671.62

Molecular Weight (Monoisotopic): 671.1864

AlogP: 0.26

#Rotatable Bonds: 7

Polar Surface Area: 243.09

Molecular Species: NEUTRAL

HBA: 14

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.75

CX Basic pKa: 3.39

CX LogP: -0.64

CX LogD: -0.66

Aromatic Rings: 6

Heavy Atoms: 49

QED Weighted: 0.10

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