S-(+)-1-(Chloromethyl)-5-hydroxy-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3-dihydro-1H-pyrrolo[3,2-f]quinoline

ID: ALA571037

Chembl Id: CHEMBL571037

PubChem CID: 44541632

Max Phase: Preclinical

Molecular Formula: C24H22ClN3O5

Molecular Weight: 467.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2cc(C(=O)N3C[C@@H](CCl)c4c3cc(O)c3ncccc43)[nH]c2c(OC)c1OC

Standard InChI:  InChI=1S/C24H22ClN3O5/c1-31-18-8-12-7-15(27-20(12)23(33-3)22(18)32-2)24(30)28-11-13(10-25)19-14-5-4-6-26-21(14)17(29)9-16(19)28/h4-9,13,27,29H,10-11H2,1-3H3/t13-/m1/s1

Standard InChI Key:  YMYUEELGWHCYLY-CYBMUJFWSA-N

Alternative Forms

1. Parent:

   

   ALA571037

   [(1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydropyrrolo[3,2-f]quinolin-3-yl]-(5,6,7-trimethoxy-1H-indol-2-yl)methanone

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: 467.91

Molecular Weight (Monoisotopic): 467.1248

AlogP: 4.43

#Rotatable Bonds: 5

Polar Surface Area: 96.91

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.47

CX Basic pKa: 4.46

CX LogP: 2.69

CX LogD: 2.65

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -0.17

References

1. Milbank JB, Stevenson RJ, Ware DC, Chang JY, Tercel M, Ahn GO, Wilson WR, Denny WA..  (2009)  Synthesis and evaluation of stable bidentate transition metal complexes of 1-(chloromethyl)-5-hydroxy-3-(5,6,7-trimethoxyindol-2-ylcarbonyl)-2,3-dihydro-1H-pyrrolo[3,2-f]quinoline (seco-6-azaCBI-TMI) as hypoxia selective cytotoxins.,  52  (21): [PMID:19821576] [10.1021/jm9008746]

Source

Source(1):

• Scientific Literature