7-Methoxy-8-[5-(7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)-pentyloxy]-1,2,3,11a-tetrahydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione

ID: ALA357270

PubChem CID: 403689

Max Phase: Preclinical

Molecular Formula: C31H36N4O7

Molecular Weight: 576.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OCCCCCOc1cc3c(cc1OC)C(=O)N1CCC[C@H]1C(=O)N3)N=C[C@@H]1CCCN1C2=O

Standard InChI:  InChI=1S/C31H36N4O7/c1-39-25-14-20-22(32-18-19-8-6-10-34(19)30(20)37)16-27(25)41-12-4-3-5-13-42-28-17-23-21(15-26(28)40-2)31(38)35-11-7-9-24(35)29(36)33-23/h14-19,24H,3-13H2,1-2H3,(H,33,36)/t19-,24-/m0/s1

Standard InChI Key:  RBMDXEFPCHVSOR-CYFREDJKSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA357270

   (6aS)-3-[5-[[(6aS)-2-methoxy-11-oxo-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]pentoxy]-2-methoxy-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-6,11-dione

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: 576.65

Molecular Weight (Monoisotopic): 576.2584

AlogP: 4.21

#Rotatable Bonds: 10

Polar Surface Area: 119.00

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.44

CX Basic pKa: 4.06

CX LogP: 3.09

CX LogD: 3.09

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.42

Np Likeness Score: 0.16

References

1. Kamal A, Ramesh G, Laxman N, Ramulu P, Srinivas O, Neelima K, Kondapi AK, Sreenu VB, Nagarajaram HA..  (2002)  Design, synthesis, and evaluation of new noncross-linking pyrrolobenzodiazepine dimers with efficient DNA binding ability and potent antitumor activity.,  45  (21): [PMID:12361394] [10.1021/jm020124h]

2. Kamal A, Ramesh G, Laxman N, Ramulu P, Srinivas O, Neelima K, Kondapi AK, Sreenu VB, Nagarajaram HA..  (2002)  Design, synthesis, and evaluation of new noncross-linking pyrrolobenzodiazepine dimers with efficient DNA binding ability and potent antitumor activity.,  45  (21): [PMID:12361394] [10.1021/jm020124h]

3. Kamal A, Tekumalla V, Raju P, Naidu VG, Diwan PV, Sistla R..  (2008)  Pyrrolo[2,1-c][1,4]benzodiazepine-beta-glucuronide prodrugs with a potential for selective therapy of solid tumors by PMT and ADEPT strategies.,  18  (13): [PMID:18538566] [10.1016/j.bmcl.2008.05.038]

4. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays