17alpha-Etynyl-17beta-13beta-[3'-(bromoacetoxy)propyl]gon-4-en-3-one

ID: ALA3250936

PubChem CID: 90674769

Max Phase: Preclinical

Molecular Formula: C24H31BrO4

Molecular Weight: 463.41

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@@]21CCCOC(=O)CBr

Standard InChI:  InChI=1S/C24H31BrO4/c1-2-24(28)12-9-21-20-6-4-16-14-17(26)5-7-18(16)19(20)8-11-23(21,24)10-3-13-29-22(27)15-25/h1,14,18-21,28H,3-13,15H2/t18-,19+,20+,21-,23-,24-/m0/s1

Standard InChI Key:  DUHQMSNEBUCOPA-OUJNNOLASA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   11.4407  -16.0756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4448  -16.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1505  -16.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1195  -18.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1195  -19.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8247  -19.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8247  -17.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5300  -18.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5266  -19.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2286  -19.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9386  -19.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2356  -17.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9421  -18.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9590  -16.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2409  -17.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6656  -17.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6523  -17.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4268  -18.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9189  -17.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5227  -17.5283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9342  -17.5366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2285  -18.7541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6441  -18.7706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6606  -16.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4124  -19.5723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8520  -16.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9505  -15.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9455  -15.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353  -14.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2304  -13.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5202  -13.4677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9356  -13.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6458  -13.8634    0.0000 Br  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  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3250936

   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]propyl 2-bromoacetate

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: 463.41

Molecular Weight (Monoisotopic): 462.1406

AlogP: 4.19

#Rotatable Bonds: 5

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: 1.65

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