18-Vinylprogesterone (18-VP)

ID: ALA1908235

PubChem CID: 9862789

Max Phase: Preclinical

Molecular Formula: C23H32O2

Molecular Weight: 340.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 18-Vinylprogesterone | 18-Vinylprogesterone|SCHEMBL4154960|CHEMBL1908235|(8S,9S,10R,13R,14S,17S)-17-acetyl-10-methyl-13-prop-2-enyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Canonical SMILES:  C=CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2C(C)=O

Standard InChI:  InChI=1S/C23H32O2/c1-4-11-23-13-10-20-18(21(23)8-7-19(23)15(2)24)6-5-16-14-17(25)9-12-22(16,20)3/h4,14,18-21H,1,5-13H2,2-3H3/t18-,19-,20+,21+,22+,23-/m1/s1

Standard InChI Key:  TZDPJVSOAZDLGP-NURQPWONSA-N

Molfile:  

     RDKit          2D

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   -3.6536   13.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391   13.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391   14.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6536   15.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3680   14.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3680   13.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   15.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2247   15.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102   16.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957   15.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957   15.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0111   14.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0111   16.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438   17.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3082   17.6518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0508   17.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957   16.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102   17.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102   18.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391   15.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825   13.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5101   15.5866    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   14.3491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957   14.3492    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  4  1  0
  4  5  1  0
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  2  3  1  0
  3  7  1  0
  8  9  1  0
  9 10  1  0
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  8  7  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 18 19  2  0
 18 20  1  0
 13 21  1  1
 21 22  1  0
 22 23  2  0
  3 24  1  1
  6 25  2  0
  8 26  1  1
  7 27  1  6
 14 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1908235

   18-Vinylprogesterone

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: 340.51

Molecular Weight (Monoisotopic): 340.2402

AlogP: 5.28

#Rotatable Bonds: 3

Polar Surface Area: 34.14

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: 4.73

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: 2.33

References

1. Fontana E, Dansette PM, Poli SM..  (2005)  Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.,  6  (1): [PMID:16248836] [10.2174/138920005774330639]

Source

Source(1):

• Scientific Literature