5-ethyl-10-fluoro-5-hydroxy-(5R)-4,5,13,15-tetrahydro-1H,3H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione

ID: ALA306796

Chembl Id: CHEMBL306796

PubChem CID: 11794148

Max Phase: Preclinical

Molecular Formula: C21H17FN2O4

Molecular Weight: 380.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@]1(O)CC(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(F)ccc3nc2-1

Standard InChI:  InChI=1S/C21H17FN2O4/c1-2-21(27)8-18(25)28-10-14-15(21)7-17-19-12(9-24(17)20(14)26)5-11-6-13(22)3-4-16(11)23-19/h3-7,27H,2,8-10H2,1H3/t21-/m1/s1

Standard InChI Key:  VJSCOIPYUQHYDB-OAQYLSRUSA-N

Alternative Forms

1. Parent:

   

   ALA306796

   (20R)-20-ethyl-7-fluoro-20-hydroxy-17-oxa-3,13-diazapentacyclo[11.9.0.02,11.04,9.015,21]docosa-1(22),2(11),3,5,7,9,15(21)-heptaene-14,18-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: 380.38

Molecular Weight (Monoisotopic): 380.1172

AlogP: 2.61

#Rotatable Bonds: 1

Polar Surface Area: 81.42

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.81

CX Basic pKa: 2.19

CX LogP: 1.30

CX LogD: 1.30

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: 0.54

References

1. Lavergne O, Demarquay D, Bailly C, Lanco C, Rolland A, Huchet M, Coulomb H, Muller N, Baroggi N, Camara J, Le Breton C, Manginot E, Cazaux JB, Bigg DC..  (2000)  Topoisomerase I-mediated antiproliferative activity of enantiomerically pure fluorinated homocamptothecins.,  43  (11): [PMID:10841808] [10.1021/jm000129j]

2. Huang Q, Wang L, Lu W..  (2013)  Evolution in medicinal chemistry of E-ring-modified Camptothecin analogs as anticancer agents.,  63  [PMID:23578545] [10.1016/j.ejmech.2013.01.058]

Source

Source(1):

• Scientific Literature