(4aS,4bR,6aS,7S,10aS,10bS,12S)-6b-(2-Bromo-acetyl)-8-cyclohexyl-5-hydroxy-6a-(R)-methyl-4a-methyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-7,9-dioxa-pentaleno[2,1-a]phenanthren-2-one

ID: ALA4874047

Cas Number: 1451396-66-9

PubChem CID: 71714735

Max Phase: Preclinical

Molecular Formula: C28H37BrO5

Molecular Weight: 533.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1C[C@H]1O[C@@H](C3CCCCC3)O[C@]12C(=O)CBr

Standard InChI:  InChI=1S/C28H37BrO5/c1-26-11-10-18(30)12-17(26)8-9-19-20-13-23-28(22(32)15-29,27(20,2)14-21(31)24(19)26)34-25(33-23)16-6-4-3-5-7-16/h10-12,16,19-21,23-25,31H,3-9,13-15H2,1-2H3/t19-,20-,21-,23+,24+,25+,26-,27-,28+/m0/s1

Standard InChI Key:  HZDQUQIAAHSDGT-ZXBNPROVSA-N

Molfile:  

 
     RDKit          2D

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    5.1692   -9.3304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1112   -7.9847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2086   -5.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9464   -6.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6358   -5.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7424   -7.2520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4585   -6.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2280   -5.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0132   -4.7790    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4874047

   Pregna-1,4-diene-3,20-dione, 21-bromo-16,17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-, (11beta,16alpha)-

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: 533.50

Molecular Weight (Monoisotopic): 532.1824

AlogP: 4.90

#Rotatable Bonds: 3

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.18

CX LogD: 5.18

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.52

Np Likeness Score: 2.13

References

1. Tsuji G, Yonemitsu K, Ito T, Yanase Y, Uema M, Ohoka N, Inoue T, Asakura H, Demizu Y..  (2021)  Development of ciclesonide analogues that block SARS-CoV-2 RNA replication.,  43  [PMID:33887440] [10.1016/j.bmcl.2021.128052]

Source

Source(1):

• Scientific Literature