17alpha-Etynyl-17beta-13beta-(3'-oxopropyl)gon-4-en-3-one

ID: ALA3250935

PubChem CID: 90674768

Max Phase: Preclinical

Molecular Formula: C22H28O3

Molecular Weight: 340.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CCC=O

Standard InChI:  InChI=1S/C22H28O3/c1-2-22(25)12-9-20-19-6-4-15-14-16(24)5-7-17(15)18(19)8-11-21(20,22)10-3-13-23/h1,13-14,17-20,25H,3-12H2/t17-,18+,19+,20-,21-,22-/m0/s1

Standard InChI Key:  LITZAYUVXCMREH-ZCPXKWAGSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.1367  -15.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1408  -15.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8465  -15.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845  -17.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1845  -18.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4865  -18.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4865  -16.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260  -17.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226  -18.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246  -18.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6347  -18.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316  -17.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382  -17.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6550  -15.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369  -16.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616  -16.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3483  -17.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228  -17.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149  -16.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187  -16.5915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303  -16.5997    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245  -17.8172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401  -17.8338    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566  -15.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8972  -18.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5480  -15.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6465  -14.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6415  -14.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468  -13.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  4  5  1  0
  4  7  1  0
  5  6  1  0
  6  9  2  0
  8  7  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  1  0
 12 15  1  0
 13 17  1  0
 16 14  1  0
 14 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
  2 16  1  0
  8 20  1  1
 13 21  1  1
 12 22  1  6
 17 23  1  6
 16 24  1  1
  5 25  2  0
  3 26  3  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3250935

   3-[(8R,9S,10R,13R,14S,17R)-17-ethynyl-17-hydroxy-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-13-yl]propanal

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: 340.46

Molecular Weight (Monoisotopic): 340.2038

AlogP: 3.45

#Rotatable Bonds: 3

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.63

CX LogD: 2.63

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: 2.10

References

1. Pitt CG, Rector DH, Cook CE, Wani MC..  (1979)  Synthesis of 11 beta,13 beta- and 13 beta,16 beta-propano steroids: probes of hormonal activity.,  22  (8): [PMID:226703] [10.1021/jm00194a016]

Source

Source(1):

• Scientific Literature