7alpha(buta-1,3-dienyl)4-androsten-17alpha-ol-3-one

ID: ALA4875435

PubChem CID: 164627404

Max Phase: Preclinical

Molecular Formula: C23H32O2

Molecular Weight: 340.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C/C=C/[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@]3(C)[C@H](O)CC[C@H]3[C@H]12

Standard InChI:  InChI=1S/C23H32O2/c1-4-5-6-15-13-16-14-17(24)9-11-22(16,2)19-10-12-23(3)18(21(15)19)7-8-20(23)25/h4-6,14-15,18-21,25H,1,7-13H2,2-3H3/b6-5+/t15-,18+,19+,20-,21+,22+,23+/m1/s1

Standard InChI Key:  BZUCOOWOGJTBHA-HFLCBZEUSA-N

Molfile:  

 
     RDKit          2D

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    3.2499   -4.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -4.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -3.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6739   -3.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6704   -4.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -4.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0960   -4.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -3.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1166   -2.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3916   -2.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8299   -2.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8165   -3.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5984   -3.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0951   -2.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6201   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5361   -4.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8081   -4.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5249   -4.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2370   -4.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9538   -4.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6666   -2.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8877   -1.4470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3791   -4.1041    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8082   -4.1207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0915   -2.8750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8249   -1.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 18  2  0
  8 19  1  6
 19 20  2  0
 20 21  1  0
 21 22  2  0
  5 23  1  1
 17 24  1  6
  9 25  1  6
 14 26  1  6
 10 27  1  1
 13 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4875435

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

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: 4.85

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.32

CX LogD: 4.32

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: 2.65

References

1. Paquin A, Oufqir Y, Sevrioukova IF, Reyes-Moreno C, Bérubé G..  (2021)  Innovative C₂-symmetric testosterone and androstenedione dimers: Design, synthesis, biological evaluation on prostate cancer cell lines and binding study to recombinant CYP3A4.,  220  [PMID:33933755] [10.1016/j.ejmech.2021.113496]

Source

Source(1):

• Scientific Literature