ID: ALA520289

Max Phase: Preclinical

Molecular Formula: C23H38N2O3

Molecular Weight: 390.57

Molecule Type: Small molecule

Representations

Synonyms (1): CarbaOZ277
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)(N)CNC(=O)CC1CC[C@]2(CC1)OC[C@]1(O2)C2CC3CC(C2)CC1C3

Standard InChI:  InChI=1S/C23H38N2O3/c1-21(2,24)13-25-20(26)12-15-3-5-22(6-4-15)27-14-23(28-22)18-8-16-7-17(10-18)11-19(23)9-16/h15-19H,3-14,24H2,1-2H3,(H,25,26)/t15?,16?,17?,18?,19?,22-,23-

Standard InChI Key:  BCIQCMGKKJSYLC-IZYRCORBSA-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: 390.57

Molecular Weight (Monoisotopic): 390.2882

AlogP: 3.36

#Rotatable Bonds: 4

Polar Surface Area: 73.58

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.63

CX LogP: 2.58

CX LogD: 0.40

Aromatic Rings: 0

Heavy Atoms: 28

QED Weighted: 0.77

Np Likeness Score: 0.87

References

1. Kaiser M, Wittlin S, Nehrbass-Stuedli A, Dong Y, Wang X, Hemphill A, Matile H, Brun R, Vennerstrom JL..  (2007)  Peroxide bond-dependent antiplasmodial specificity of artemisinin and OZ277 (RBx11160).,  51  (8): [PMID:17562801] [10.1128/aac.00225-07]

2. Rubio BK, Tenney K, Ang KH, Abdulla M, Arkin M, McKerrow JH, Crews P..  (2009)  The marine sponge Diacarnus bismarckensis as a source of peroxiterpene inhibitors of Trypanosoma brucei, the causative agent of sleeping sickness.,  72  (2): [PMID:19159277] [10.1021/np800711a]

3. Fügi MA, Wittlin S, Dong Y, Vennerstrom JL..  (2010)  Probing the antimalarial mechanism of artemisinin and OZ277 (arterolane) with nonperoxidic isosteres and nitroxyl radicals.,  54  (3): [PMID:20028825] [10.1128/aac.01305-09]

Source

Source(1):

• Scientific Literature