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

ID: ALA447330

Chembl Id: CHEMBL447330

PubChem CID: 44565951

Max Phase: Preclinical

Molecular Formula: C33H27BrN4O10

Molecular Weight: 719.50

Molecule Type: Small molecule

Associated Items:

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(Br)cc1

Standard InChI:  InChI=1S/C33H27BrN4O10/c34-14-3-1-13(2-4-14)11-35-37-31(45)24-22-17-7-5-15(40)9-19(17)36-26(22)27-23(25(24)32(37)46)18-8-6-16(41)10-20(18)38(27)48-33-30(44)29(43)28(42)21(12-39)47-33/h1-10,21,28-30,33,35-36,39-44H,11-12H2/t21-,28-,29+,30-,33+/m1/s1

Standard InChI Key:  MCESCZGPCRHNSV-OJSVXGLKSA-N

Associated Targets(Human)

MKN-45 (2102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DLD-1 (17511 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

P388/S (109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Top1 DNA topoisomerase I (53 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 719.50Molecular Weight (Monoisotopic): 718.0911AlogP: 2.13#Rotatable Bonds: 6
Polar Surface Area: 209.97Molecular Species: NEUTRALHBA: 12HBD: 8
#RO5 Violations: 3HBA (Lipinski): 14HBD (Lipinski): 8#RO5 Violations (Lipinski): 3
CX Acidic pKa: 8.75CX Basic pKa: 2.78CX LogP: 2.03CX LogD: 2.01
Aromatic Rings: 6Heavy Atoms: 48QED Weighted: 0.12Np Likeness Score: 0.64

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