Benzo[b]thiophene-2-carboxylic acid [2-((S)-8-chloromethyl-4-hydroxy-1-methyl-7,8-dihydro-furo[3,2-e]indole-6-carbonyl)-1H-indol-5-yl]-amide

ID: ALA79039

PubChem CID: 10053422

Max Phase: Preclinical

Molecular Formula: C30H22ClN3O4S

Molecular Weight: 556.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1coc2c(O)cc3c(c12)[C@H](CCl)CN3C(=O)c1cc2cc(NC(=O)c3cc4ccccc4s3)ccc2[nH]1

Standard InChI:  InChI=1S/C30H22ClN3O4S/c1-15-14-38-28-23(35)11-22-27(26(15)28)18(12-31)13-34(22)30(37)21-9-17-8-19(6-7-20(17)33-21)32-29(36)25-10-16-4-2-3-5-24(16)39-25/h2-11,14,18,33,35H,12-13H2,1H3,(H,32,36)/t18-/m1/s1

Standard InChI Key:  LMVPFQJEECCLHM-GOSISDBHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA79039

   N-[2-[(8S)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydrofuro[3,2-e]indole-6-carbonyl]-1H-indol-5-yl]-1-benzothiophene-2-carboxamide

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: 556.04

Molecular Weight (Monoisotopic): 555.1020

AlogP: 7.38

#Rotatable Bonds: 4

Polar Surface Area: 98.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.16

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 5.35

Aromatic Rings: 6

Heavy Atoms: 39

QED Weighted: 0.20

Np Likeness Score: -0.88

References

1. Mohamadi F, Spees MM, Staten GS, Marder P, Kipka JK, Johnson DA, Boger DL, Zarrinmayeh H..  (1994)  Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines: an asymmetric hydroboration mediated synthesis of the alkylation subunits.,  37  (2): [PMID:8295210] [10.1021/jm00028a005]

Source

Source(1):

• Scientific Literature