ID: ALA72832

Max Phase: Preclinical

Molecular Formula: C21H18N2O4

Molecular Weight: 362.39

Molecule Type: Small molecule

Representations

Synonyms (1): BN-80245
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCC1(O)CC(=O)OCc2c1cc1n(c2=O)Cc2cc3ccccc3nc2-1

Standard InChI:  InChI=1S/C21H18N2O4/c1-2-21(26)9-18(24)27-11-14-15(21)8-17-19-13(10-23(17)20(14)25)7-12-5-3-4-6-16(12)22-19/h3-8,26H,2,9-11H2,1H3

Standard InChI Key:  PAEZRCINULFAGO-UHFFFAOYSA-N

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

Properties

Molecular Weight: 362.39

Molecular Weight (Monoisotopic): 362.1267

AlogP: 2.47

#Rotatable Bonds: 1

Polar Surface Area: 81.42

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.81

CX Basic pKa: 3.08

CX LogP: 1.15

CX LogD: 1.15

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: 0.90

References

1. Lavergne O, Lesueur-Ginot L, Rodas FP, Bigg DC.  (1997)  BN 80245: An E-ring modified camptothecin with potent antiproliferative and topoisomerase I inhibitory activities,  7  (17): [10.1016/S0960-894X(97)00398-3]

2. Lavergne O, Lesueur-Ginot L, Pla Rodas F, Kasprzyk PG, Pommier J, Demarquay D, Prévost G, Ulibarri G, Rolland A, Schiano-Liberatore AM, Harnett J, Pons D, Camara J, Bigg DC..  (1998)  Homocamptothecins: synthesis and antitumor activity of novel E-ring-modified camptothecin analogues.,  41  (27): [PMID:9876111] [10.1021/jm980400l]

3. 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