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Compounds
ALA1834993

1-(chloromethyl)-3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-N-(2-hydroxyethyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamide

ID: ALA1834993

Chembl Id: CHEMBL1834993

PubChem CID: 11527365

Max Phase: Preclinical

Molecular Formula: C28H30ClN5O7S

Molecular Weight: 616.10

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CN(C)CCOc1ccc2[nH]c(C(=O)N3CC(CCl)c4c3cc([N+](=O)[O-])c3cc(S(=O)(=O)NCCO)ccc43)cc2c1

Standard InChI: InChI=1S/C28H30ClN5O7S/c1-32(2)8-10-41-19-3-6-23-17(11-19)12-24(31-23)28(36)33-16-18(15-29)27-21-5-4-20(42(39,40)30-7-9-35)13-22(21)25(34(37)38)14-26(27)33/h3-6,11-14,18,30-31,35H,7-10,15-16H2,1-2H3

Standard InChI Key: KRUNPKDABQVLHA-UHFFFAOYSA-N

Alternative Forms

Parent:

ALA1834993
1-(Chloromethyl)-3-{5-[2-(dimethylamino)ethoxy]indol-2-carbonyl}-N-(2-hydroxyethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

Associated Targets(Human)

HT-29 (80576 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SiHa (2051 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

UV4 (255 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 616.10	Molecular Weight (Monoisotopic): 615.1554	AlogP: 3.42	#Rotatable Bonds: 11
Polar Surface Area: 158.11	Molecular Species: BASE	HBA: 8	HBD: 3
#RO5 Violations: 1	HBA (Lipinski): 12	HBD (Lipinski): 3	#RO5 Violations (Lipinski): 2
CX Acidic pKa: 9.99	CX Basic pKa: 8.72	CX LogP: 2.01	CX LogD: 0.88
Aromatic Rings: 4	Heavy Atoms: 42	QED Weighted: 0.13	Np Likeness Score: -1.17

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]
2. Stevenson RJ, Denny WA, Tercel M, Pruijn FB, Ashoorzadeh A.. (2012) Nitro seco analogues of the duocarmycins containing sulfonate leaving groups as hypoxia-activated prodrugs for cancer therapy., 55 (6): [PMID:22339090] [10.1021/jm201717y]
3. Tercel M, Lee HH, Mehta SY, Youte Tendoung JJ, Bai SY, Liyanage HDS, Pruijn FB.. (2017) Influence of a Basic Side Chain on the Properties of Hypoxia-Selective Nitro Analogues of the Duocarmycins: Demonstration of Substantial Anticancer Activity in Combination with Irradiation or Chemotherapy., 60 (13): [PMID:28644035] [10.1021/acs.jmedchem.7b00563]

Source

Source(1):

Scientific Literature