(6aS,12aR)-2,3-Dimethoxy-6-methyl-6a,12a-dihydro-6H-8,10-dioxa-6-aza-benzo[a]cyclopenta[h]fluorene-5,12-dione

ID: ALA439615

Chembl Id: CHEMBL439615

PubChem CID: 335395

Max Phase: Preclinical

Molecular Formula: C20H17NO6

Molecular Weight: 367.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)[C@H]1C(=O)c3cc4c(cc3[C@H]1N(C)C2=O)OCO4

Standard InChI:  InChI=1S/C20H17NO6/c1-21-18-10-5-15-16(27-8-26-15)6-11(10)19(22)17(18)9-4-13(24-2)14(25-3)7-12(9)20(21)23/h4-7,17-18H,8H2,1-3H3/t17-,18-/m1/s1

Standard InChI Key:  XMGPGUJCNJAHRG-QZTJIDSGSA-N

Alternative Forms

1. Parent:

   

   ALA439615

   (1S,12R)-15,16-dimethoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaene-11,19-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: 367.36

Molecular Weight (Monoisotopic): 367.1056

AlogP: 2.54

#Rotatable Bonds: 2

Polar Surface Area: 74.30

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.56

CX LogD: 1.56

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.81

Np Likeness Score: 0.58

References

1. Strumberg D, Pommier Y, Paull K, Jayaraman M, Nagafuji P, Cushman M..  (1999)  Synthesis of cytotoxic indenoisoquinoline topoisomerase I poisons.,  42  (3): [PMID:9986716] [10.1021/jm9803323]

2. Xiao X, Miao ZH, Antony S, Pommier Y, Cushman M..  (2005)  Dihydroindenoisoquinolines function as prodrugs of indenoisoquinolines.,  15  (11): [PMID:15911256] [10.1016/j.bmcl.2005.03.101]

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays