carbaOZ277

ID: ALA520289

PubChem CID: 44568138

Max Phase: Preclinical

Molecular Formula: C23H38N2O3

Molecular Weight: 390.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CarbaOZ277 | CarbaOZ277|CHEMBL520289

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

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   -1.7461   -7.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -7.1726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9703   -7.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531   -8.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964   -8.5033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349   -7.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228   -8.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4951   -8.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881   -7.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -7.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357   -7.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1541   -8.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9779   -8.5653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -9.2899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833   -7.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -7.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0277   -7.8402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2032   -7.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -8.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4932   -8.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6749   -8.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6617   -8.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0805   -8.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0363   -9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3114   -8.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047   -8.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733   -7.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4360   -7.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
  2  3  1  0
 13 15  1  0
  4  3  1  1
 15 16  1  0
  4  5  1  0
 16 17  1  0
  6 10  1  0
 16 18  1  0
  1  7  1  0
 16 19  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5  1  1  0
  9 11  1  0
  6  1  1  0
 11 12  1  0
  1  2  1  1
 12 13  1  0
 20 21  1  0
 20 22  1  0
 21 23  1  0
 22 24  1  0
 23 25  1  0
 24 25  1  0
 26 27  1  0
 22 26  1  0
 21 28  1  0
 25  4  1  0
  4 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA520289

   CarbaOZ277

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: 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: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.63

CX LogP: 2.58

CX LogD: 0.40

Aromatic Rings: ┄

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