1-(Bromomethyl)-N-(2-hydroxyethyl)-5-nitro-3-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-2,3-dihydro-1Hbenzo[e]indole-7-sulfonamide

ID: ALA1834932

Chembl Id: CHEMBL1834932

PubChem CID: 56683129

Max Phase: Preclinical

Molecular Formula: C27H27BrN4O9S

Molecular Weight: 663.50

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cc2cc(C(=O)N3CC(CBr)c4c3cc([N+](=O)[O-])c3cc(S(=O)(=O)NCCO)ccc43)[nH]c2c(OC)c1OC

Standard InChI:  InChI=1S/C27H27BrN4O9S/c1-39-22-9-14-8-19(30-24(14)26(41-3)25(22)40-2)27(34)31-13-15(12-28)23-17-5-4-16(42(37,38)29-6-7-33)10-18(17)20(32(35)36)11-21(23)31/h4-5,8-11,15,29-30,33H,6-7,12-13H2,1-3H3

Standard InChI Key:  MLDRXLUHEDTBSX-UHFFFAOYSA-N

Associated Targets(Human)

HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SiHa (2051 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

UV4 (255 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: 663.50Molecular Weight (Monoisotopic): 662.0682AlogP: 3.66#Rotatable Bonds: 10
Polar Surface Area: 173.33Molecular Species: NEUTRALHBA: 9HBD: 3
#RO5 Violations: 1HBA (Lipinski): 13HBD (Lipinski): 3#RO5 Violations (Lipinski): 2
CX Acidic pKa: 9.96CX Basic pKa: CX LogP: 2.09CX LogD: 2.09
Aromatic Rings: 4Heavy Atoms: 42QED Weighted: 0.13Np Likeness Score: -0.70

References

1. Stevenson RJ, Denny WA, Ashoorzadeh A, Pruijn FB, van Leeuwen WF, Tercel M..  (2011)  The effect of a bromide leaving group on the properties of nitro analogs of the duocarmycins as hypoxia-activated prodrugs and phosphate pre-prodrugs for antitumor therapy.,  19  (20): [PMID:21920763] [10.1016/j.bmc.2011.08.045]

Source