1H-Indole-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: ALA80340

PubChem CID: 10324970

Max Phase: Preclinical

Molecular Formula: C30H23ClN4O4

Molecular Weight: 538.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1coc2c(O)cc3c(c12)[C@H](CCl)CN3C(=O)c1cc2cc(NC(=O)c3cc4ccccc4[nH]3)ccc2[nH]1

Standard InChI:  InChI=1S/C30H23ClN4O4/c1-15-14-39-28-25(36)11-24-27(26(15)28)18(12-31)13-35(24)30(38)23-10-17-8-19(6-7-21(17)34-23)32-29(37)22-9-16-4-2-3-5-20(16)33-22/h2-11,14,18,33-34,36H,12-13H2,1H3,(H,32,37)/t18-/m1/s1

Standard InChI Key:  NGNYYOJUGIBULM-GOSISDBHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA80340

   N-[2-[(8S)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydrofuro[3,2-e]indole-6-carbonyl]-1H-indol-5-yl]-1H-indole-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: 538.99

Molecular Weight (Monoisotopic): 538.1408

AlogP: 6.64

#Rotatable Bonds: 4

Polar Surface Area: 114.36

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.16

CX Basic pKa: ┄

CX LogP: 4.79

CX LogD: 4.36

Aromatic Rings: 6

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: -0.48

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