ID: ALA74190

Max Phase: Preclinical

Molecular Formula: C21H18N2O4

Molecular Weight: 362.39

Molecule Type: Small molecule

Representations

Synonyms (1): Homocamptothecin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC[C@@]1(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/t21-/m1/s1

Standard InChI Key:  PAEZRCINULFAGO-OAQYLSRUSA-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, 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. 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. Giannini G, Marzi M, Cabri W, Marastoni E, Battistuzzi G, Vesci L, Pisano C, Beretta GL, De Cesare M, Zunino F..  (2008)  E-ring-modified 7-oxyiminomethyl camptothecins: Synthesis and preliminary in vitro and in vivo biological evaluation.,  18  (9): [PMID:18424133] [10.1016/j.bmcl.2008.03.074]

4. 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