Allylestrenol

ID: ALA2105618

PubChem CID: 70695647

Product Number: R671262, Order Now?

Max Phase: Approved

Molecular Formula: C21H32O

Molecular Weight: 300.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Allyloestrenol | Perselin | NSC-37723 | Perselin|CHEMBL2105618

Trade Names(1): Gestanin

Canonical SMILES:  C=CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCCC4[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16?,17-,18-,19+,20+,21+/m1/s1

Standard InChI Key:  ATXHVCQZZJYMCF-XZCODKSBSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    5.9202   -1.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9202   -2.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2043   -2.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -2.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663   -2.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7463   -1.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663   -3.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2043   -1.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -1.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8320   -2.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2043   -3.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -4.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3643   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504   -4.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9349   -0.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504   -2.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -3.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -2.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1619   -3.2711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2043   -1.9127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822   -3.2436    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7463   -0.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4607   -0.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4607    0.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5143   -0.9690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  9  1  0
  5  4  1  0
  1  6  1  0
  5  7  1  0
  1  8  1  0
  9  8  1  0
  2 10  1  0
  3 11  1  0
 12 11  1  0
  6 13  1  0
 14  7  2  0
  1 15  1  1
  5 16  1  0
 17 18  1  0
 18 16  1  0
  2 19  1  6
  3 20  1  1
  4 21  1  6
 10 13  1  0
  4  3  1  0
 12  7  1  0
 14 17  1  0
  6 22  1  6
 22 23  1  0
 23 24  2  0
  6 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2105618

   (8R,9S,13S,14S,17R)-13-methyl-17-prop-2-enyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

Molecule Features

Natural Product: Yes

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: 300.49

Molecular Weight (Monoisotopic): 300.2453

AlogP: 5.26

#Rotatable Bonds: 2

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.83

CX LogD: 4.83

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: 2.14

References

1. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. WHO Anatomical Therapeutic Chemical Classification, 

4. British National Formulary (72nd edition), 

5. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(4):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary