ID: ALA120835

Max Phase: Preclinical

Molecular Formula: C20H13ClN2O6

Molecular Weight: 412.79

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  O=C1c2cc3c(cc2-c2c1c1ccc([N+](=O)[O-])cc1c(=O)n2CCCCl)OCO3

Standard InChI:  InChI=1S/C20H13ClN2O6/c21-4-1-5-22-18-12-7-15-16(29-9-28-15)8-13(12)19(24)17(18)11-3-2-10(23(26)27)6-14(11)20(22)25/h2-3,6-8H,1,4-5,9H2

Standard InChI Key:  SDOYHGOHOXTXFO-UHFFFAOYSA-N

Associated Targets(Human)

HOP-62 47048 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

HCT-116 91556 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

SF-268 49410 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

UACC-62 47335 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

OVCAR-3 48710 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

SN12C 47755 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

DU-145 51482 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

MDA-MB-435 38290 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

DNA topoisomerase I 7553 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Cell line 371 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

Properties

Molecular Weight: 412.79Molecular Weight (Monoisotopic): 412.0462AlogP: 3.48#Rotatable Bonds: 4
Polar Surface Area: 100.67Molecular Species: NEUTRALHBA: 7HBD: 0
#RO5 Violations: 0HBA (Lipinski): 8HBD (Lipinski): 0#RO5 Violations (Lipinski): 0
CX Acidic pKa: CX Basic pKa: CX LogP: 2.41CX LogD: 2.41
Aromatic Rings: 3Heavy Atoms: 29QED Weighted: 0.29Np Likeness Score: -0.21

References

1. Morrell A, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2004)  Synthesis of nitrated indenoisoquinolines as topoisomerase I inhibitors.,  14  (14): [PMID:15203138] [10.1016/j.bmcl.2004.05.022]
2. Xiao X, Antony S, Pommier Y, Cushman M..  (2005)  On the binding of indeno[1,2-c]isoquinolines in the DNA-topoisomerase I cleavage complex.,  48  (9): [PMID:15857129] [10.1021/jm050017y]
3. Xiao X, Miao ZH, Antony S, Pommier Y, Cushman M..  (2005)  Dihydroindenoisoquinolines function as prodrugs of indenoisoquinolines.,  15  (11): [PMID:15911256] [10.1016/j.bmcl.2005.03.101]

Source