TETRAHYDROCORTISONE-21-ACETATE

ID: ALA3138721

Cas Number: 17736-20-8

PubChem CID: 223685

Max Phase: Preclinical

Molecular Formula: C23H34O6

Molecular Weight: 406.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H34O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h14-17,20,25,28H,4-12H2,1-3H3/t14-,15-,16+,17+,20-,21+,22+,23+/m1/s1

Standard InChI Key:  MULICLCRGFYQJF-LLTWYMBTSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
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    0.0719   -4.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839   -4.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839   -2.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4959   -3.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970   -4.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2080   -4.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226   -4.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059   -2.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234   -3.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222   -1.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022   -2.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6397   -2.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6366   -2.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4245   -3.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9147   -2.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296   -1.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -4.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -2.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4927   -5.0448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344   -1.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010   -3.8073    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6302   -3.8114    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9177   -2.5698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4873   -1.7452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296   -1.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2265   -1.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8099   -2.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4400   -0.8942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6067   -2.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1901   -2.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9870   -2.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9766   -3.4411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 13 14  1  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  5  9  1  0
  6  7  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  7  8  1  0
  2 18  1  6
  8 10  1  0
  5 19  1  1
  9 10  1  0
  6 20  1  1
  3  6  1  0
 13 21  1  1
  5  4  1  0
  5  6  1  0
  9 12  1  0
  9 22  1  6
 10 14  1  0
 14 23  1  6
 13 11  1  0
 10 24  1  1
 12 25  2  0
 17 26  1  6
 17 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3138721

   3alpha,17,21-Trihydroxy-5beta-pregnane-11,20-dione 21-acetate

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: 406.52

Molecular Weight (Monoisotopic): 406.2355

AlogP: 2.43

#Rotatable Bonds: 3

Polar Surface Area: 100.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.60

CX Basic pKa: ┄

CX LogP: 1.94

CX LogD: 1.94

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: 2.15

References

1. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

Source

Source(1):

• Scientific Literature