Methyl (S)-5-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)butanamido)-1-methyl-1H-pyrrole-2-carboxamido)benzo[b]thiophene-2-carboxylate

ID: ALA5176343

Chembl Id: CHEMBL5176343

PubChem CID: 72202685

Max Phase: Preclinical

Molecular Formula: C33H33N5O7S

Molecular Weight: 643.72

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc2cc(NC(=O)c3cc(NC(=O)CCCOc4cc5c(cc4OC)C(=O)N4CCC[C@H]4C=N5)cn3C)ccc2s1

Standard InChI:  InChI=1S/C33H33N5O7S/c1-37-18-21(14-25(37)31(40)36-20-8-9-28-19(12-20)13-29(46-28)33(42)44-3)35-30(39)7-5-11-45-27-16-24-23(15-26(27)43-2)32(41)38-10-4-6-22(38)17-34-24/h8-9,12-18,22H,4-7,10-11H2,1-3H3,(H,35,39)(H,36,40)/t22-/m0/s1

Standard InChI Key:  DGDFSWDJACGDBE-QFIPXVFZSA-N

Alternative Forms

1. Parent:

   

   ALA5176343

   methyl 5-[[4-[4-[[(6aS)-2-methoxy-11-oxo-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]butanoylamino]-1-methylpyrrole-2-carbonyl]amino]-1-benzothiophene-2-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 643.72

Molecular Weight (Monoisotopic): 643.2101

AlogP: 5.41

#Rotatable Bonds: 10

Polar Surface Area: 140.56

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 13.63

CX Basic pKa: 4.06

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 4

Heavy Atoms: 46

QED Weighted: 0.17

Np Likeness Score: -0.89

References

1. 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