16alpha-hydroxy prednisolone

ID: ALA3542319

Cas Number: 13951-70-7

PubChem CID: 11047056

Product Number: T302804, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H28O6

Molecular Weight: 376.45

Molecule Type: Small molecule

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](O)[C@]2(O)C(=O)CO

Standard InChI:  InChI=1S/C21H28O6/c1-19-6-5-12(23)7-11(19)3-4-13-14-8-16(25)21(27,17(26)10-22)20(14,2)9-15(24)18(13)19/h5-7,13-16,18,22,24-25,27H,3-4,8-10H2,1-2H3/t13-,14-,15-,16+,18+,19-,20-,21-/m0/s1

Standard InChI Key:  SEKYBDYVXDAYPY-ILNISADRSA-N

Molfile:  

     RDKit          2D

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    7.5122   -5.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3689   -6.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2999   -5.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7950   -6.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5040   -6.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0695   -6.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3689   -7.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7950   -5.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7809   -6.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7950   -7.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1167   -5.3771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5040   -4.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3689   -5.2113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3564   -6.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2875   -3.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6938   -3.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4915   -7.2718    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7867   -6.0446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0695   -7.2635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6058   -6.0562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3 12  1  1
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 20 17  2  0
 21  3  1  0
  1 22  1  1
  9 23  1  1
  2 24  1  1
 25 12  1  0
 26 25  1  0
  5 27  1  6
  4 28  1  1
  6 29  1  6
 14 13  1  0
  4  6  1  0
  7 18  1  0
 11 17  1  0
 13 30  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3542319

   11a,16b,17,21-Tetrahydroxy-pregna-1,4-diene-3,20-dione

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: 376.45

Molecular Weight (Monoisotopic): 376.1886

AlogP: 0.53

#Rotatable Bonds: 2

Polar Surface Area: 115.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.76

CX Basic pKa: ┄

CX LogP: 0.20

CX LogD: 0.20

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.56

Np Likeness Score: 2.54

References

1. Moore CD, Roberts JK, Orton CR, Murai T, Fidler TP, Reilly CA, Ward RM, Yost GS..  (2013)  Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes.,  41  (2): [PMID:23143891] [10.1124/dmd.112.046318]

Source

Source(1):

• Scientific Literature