(2-{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}-ethyl)-phosphonic acid diethyl ester

ID: ALA458396

Chembl Id: CHEMBL458396

PubChem CID: 44567238

Max Phase: Preclinical

Molecular Formula: C26H41N4O6P

Molecular Weight: 536.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(CCN1CCN(CCCOc2cc3c(cc2OC)C(=O)N2CCC[C@H]2C=N3)CC1)OCC

Standard InChI:  InChI=1S/C26H41N4O6P/c1-4-35-37(32,36-5-2)17-15-29-13-11-28(12-14-29)9-7-16-34-25-19-23-22(18-24(25)33-3)26(31)30-10-6-8-21(30)20-27-23/h18-21H,4-17H2,1-3H3/t21-/m0/s1

Standard InChI Key:  LPJNVPKBCLZBHZ-NRFANRHFSA-N

Alternative Forms

1. Parent:

   

   ALA458396

   (6aS)-3-[3-[4-(2-diethoxyphosphorylethyl)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: 536.61

Molecular Weight (Monoisotopic): 536.2764

AlogP: 3.67

#Rotatable Bonds: 13

Polar Surface Area: 93.14

Molecular Species: BASE

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.69

CX LogP: 1.22

CX LogD: -0.09

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.28

Np Likeness Score: -0.20

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