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

ID: ALA464682

Chembl Id: CHEMBL464682

PubChem CID: 25113728

Max Phase: Preclinical

Molecular Formula: C28H45N4O6P

Molecular Weight: 564.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=O)(CCN1CCN(CCCCCOc2cc3c(cc2OC)C(=O)N2CCC[C@H]2C=N3)CC1)OCC

Standard InChI:  InChI=1S/C28H45N4O6P/c1-4-37-39(34,38-5-2)19-17-31-15-13-30(14-16-31)11-7-6-8-18-36-27-21-25-24(20-26(27)35-3)28(33)32-12-9-10-23(32)22-29-25/h20-23H,4-19H2,1-3H3/t23-/m0/s1

Standard InChI Key:  COOVHJHQCPOPQQ-QHCPKHFHSA-N

Alternative Forms

1. Parent:

   

   ALA464682

   diethyl 2-[4-(5-[(11aS)-7-methoxy-5-oxo-2,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl]oxypentyl)piperazino]ethylphosphonate

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: 564.66

Molecular Weight (Monoisotopic): 564.3077

AlogP: 4.45

#Rotatable Bonds: 15

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: 8.77

CX LogP: 2.12

CX LogD: 0.73

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.23

Np Likeness Score: -0.14

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