(S)-Methyl 4-(4-(4-(4-((7-Methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)butanamido)-1-methyl-1H-pyrrole-2-carboxamido)phenyl)-1-methyl-1H-pyrrole-2-carboxylate

ID: ALA2321905

Chembl Id: CHEMBL2321905

PubChem CID: 71606413

Max Phase: Preclinical

Molecular Formula: C36H38N6O7

Molecular Weight: 666.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(-c2ccc(NC(=O)c3cc(NC(=O)CCCOc4cc5c(cc4OC)C(=O)N4CCC[C@H]4C=N5)cn3C)cc2)cn1C

Standard InChI:  InChI=1S/C36H38N6O7/c1-40-20-23(15-30(40)36(46)48-4)22-9-11-24(12-10-22)39-34(44)29-16-25(21-41(29)2)38-33(43)8-6-14-49-32-18-28-27(17-31(32)47-3)35(45)42-13-5-7-26(42)19-37-28/h9-12,15-21,26H,5-8,13-14H2,1-4H3,(H,38,43)(H,39,44)/t26-/m0/s1

Standard InChI Key:  OVVDVKXCZRNFHP-SANMLTNESA-N

Alternative Forms

1. Parent:

   

   ALA2321905

   (S)-methyl 4-(4-(4-(4-(7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-8-yloxy)butanamido)-1-methyl-1H-pyrrole-2-carboxamido)phenyl)-1-methyl-1H-pyrrole-2-carboxylate

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: 666.74

Molecular Weight (Monoisotopic): 666.2802

AlogP: 5.20

#Rotatable Bonds: 11

Polar Surface Area: 145.49

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 13.64

CX Basic pKa: 4.06

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 4

Heavy Atoms: 49

QED Weighted: 0.17

Np Likeness Score: -0.57

References

1. Rahman KM, Jackson PJ, James CH, Basu BP, Hartley JA, de la Fuente M, Schatzlein A, Robson M, Pedley RB, Pepper C, Fox KR, Howard PW, Thurston DE..  (2013)  GC-targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models.,  56  (7): [PMID:23514599] [10.1021/jm301882a]

2. Joseph AM, Nahar K, Daw S, Hasan MM, Lo R, Le TBK, Rahman KM, Badrinarayanan A..  (2022)  Mechanistic insight into the repair of C8-linked pyrrolobenzodiazepine monomer-mediated DNA damage.,  13  (12.0): [PMID:36561066] [10.1039/d2md00194b]

Source

Source(1):

• Scientific Literature