6-Allyl-2,3-dimethoxy-6a,12a-dihydro-6H-8,10-dioxa-6-aza-benzo[a]cyclopenta[h]fluorene-5,12-dione

ID: ALA315113

Chembl Id: CHEMBL315113

PubChem CID: 10691956

Max Phase: Preclinical

Molecular Formula: C22H19NO6

Molecular Weight: 393.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1C(=O)c2cc(OC)c(OC)cc2[C@H]2C(=O)c3cc4c(cc3[C@H]21)OCO4

Standard InChI:  InChI=1S/C22H19NO6/c1-4-5-23-20-12-7-17-18(29-10-28-17)8-13(12)21(24)19(20)11-6-15(26-2)16(27-3)9-14(11)22(23)25/h4,6-9,19-20H,1,5,10H2,2-3H3/t19-,20-/m1/s1

Standard InChI Key:  VUSLGSIKCKVEDQ-WOJBJXKFSA-N

Alternative Forms

1. Parent:

   

   ALA315113

   (1S,12R)-15,16-dimethoxy-20-prop-2-enyl-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: 393.40

Molecular Weight (Monoisotopic): 393.1212

AlogP: 3.10

#Rotatable Bonds: 4

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: 2.29

CX LogD: 2.29

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: 0.38

References

1. Jayaraman M, Fox BM, Hollingshead M, Kohlhagen G, Pommier Y, Cushman M..  (2002)  Synthesis of new dihydroindeno[1,2-c]isoquinoline and indenoisoquinolinium chloride topoisomerase I inhibitors having high in vivo anticancer activity in the hollow fiber animal model.,  45  (1): [PMID:11754595] [10.1021/jm000498f]

2. 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]

3. 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]

Source

Source(1):

• Scientific Literature