(3-{4-[3-((S)-7-Methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)-propyl]-piperazin-1-yl}-propyl)-phosphonic acid diethyl ester

ID: ALA463474

Chembl Id: CHEMBL463474

PubChem CID: 44567239

Max Phase: Preclinical

Molecular Formula: C27H43N4O6P

Molecular Weight: 550.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(CCCN1CCN(CCCOc2cc3c(cc2OC)C(=O)N2CCC[C@H]2C=N3)CC1)OCC

Standard InChI:  InChI=1S/C27H43N4O6P/c1-4-36-38(33,37-5-2)18-8-11-30-15-13-29(14-16-30)10-7-17-35-26-20-24-23(19-25(26)34-3)27(32)31-12-6-9-22(31)21-28-24/h19-22H,4-18H2,1-3H3/t22-/m0/s1

Standard InChI Key:  PVBLRHUACWQHFD-QFIPXVFZSA-N

Alternative Forms

1. Parent:

   

   ALA463474

   (6aS)-3-[3-[4-(3-diethoxyphosphorylpropyl)piperazin-1-yl]propoxy]-2-methoxy-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one

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: 550.64

Molecular Weight (Monoisotopic): 550.2920

AlogP: 4.06

#Rotatable Bonds: 14

Polar Surface Area: 93.14

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.15

CX LogP: 1.37

CX LogD: 0.55

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.25

Np Likeness Score: -0.21

References

1. Kamal A, Kumar PP, Seshadri BN, Srinivas O, Kumar MS, Sen S, Kurian N, Juvekar AS, Zingde SM..  (2008)  Phosphonate-linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates: synthesis, DNA-binding affinity and cytotoxicity.,  16  (7): [PMID:18262426] [10.1016/j.bmc.2008.01.040]

Source

Source(1):

• Scientific Literature