(4aS,6aS,6bR,8aR,12aS,12bR,14bS)-methyl 10-(hydroxyimino)-2,2,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

ID: ALA4280054

PubChem CID: 49787176

Max Phase: Preclinical

Molecular Formula: C31H47NO4

Molecular Weight: 497.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC(=O)[C@@H]3[C@@]4(C)CC/C(=N\O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2

Standard InChI:  InChI=1S/C31H47NO4/c1-26(2)13-15-31(25(34)36-8)16-14-29(6)19(20(31)18-26)17-21(33)24-28(5)11-10-23(32-35)27(3,4)22(28)9-12-30(24,29)7/h17,20,22,24,35H,9-16,18H2,1-8H3/b32-23+/t20-,22-,24+,28-,29+,30+,31-/m0/s1

Standard InChI Key:  DEQYIRIAIXPQTG-DNDMAMFESA-N

Molfile:  

     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
   25.0069  -14.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4196  -15.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8280  -14.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5524  -19.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1479  -19.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7390  -19.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4463  -17.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4463  -18.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1516  -17.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8568  -17.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8534  -18.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5554  -19.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2655  -18.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5624  -17.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2651  -17.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2818  -16.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5677  -16.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9845  -16.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9708  -17.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6646  -17.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3765  -17.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6920  -16.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3859  -16.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0951  -16.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1166  -15.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7073  -15.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6850  -17.1197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.2569  -17.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8495  -17.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7387  -19.1341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0882  -17.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0857  -17.9534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7972  -16.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5553  -18.3166    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.9627  -18.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0600  -19.5094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.5036  -17.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8640  -16.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0309  -18.7257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  7  9  1  0
  8  5  1  0
  5 11  1  0
 10  9  1  0
 10 11  1  0
 10 14  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 14 15  1  0
 14 17  1  0
 15 19  1  0
 18 16  2  0
 16 17  1  0
 18 19  1  0
 18 22  1  0
 19 20  1  0
 20 21  1  0
 21 23  1  0
 22 23  1  0
 22 26  1  0
 23 24  1  0
 24 25  1  0
 25  2  1  0
  2 26  1  0
 22 27  1  1
 15 28  1  1
 10 29  1  1
  8 30  2  0
 23 31  1  1
 31 32  2  0
 31 33  1  0
 14 34  1  6
 19 35  1  6
 11 36  1  6
 33 37  1  0
 17 38  2  0
 30 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4280054

   methyl (4aS,6aR,6aS,6bR,8aR,10E,12aS,14bS)-10-hydroxyimino-2,2,6a,6b,9,9,12a-heptamethyl-13-oxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-4a-carboxylate

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: 497.72

Molecular Weight (Monoisotopic): 497.3505

AlogP: 6.97

#Rotatable Bonds: 1

Polar Surface Area: 75.96

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.36

CX Basic pKa: 2.20

CX LogP: 6.75

CX LogD: 6.75

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.24

Np Likeness Score: 2.91

References

1. Salvador JAR, Leal AS, Valdeira AS, Gonçalves BMF, Alho DPS, Figueiredo SAC, Silvestre SM, Mendes VIS..  (2017)  Oleanane-, ursane-, and quinone methide friedelane-type triterpenoid derivatives: Recent advances in cancer treatment.,  142  [PMID:28754470] [10.1016/j.ejmech.2017.07.013]

Source

Source(1):

• Scientific Literature