21-Dehydrocortisone

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Basic information

CAS: 16574-04-2
Standard SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)C=O
InChIKey: DJLICGGNASJAQR-ZPOLXVRWSA-N
Molecular formula: C21H26O5
Average molar mass: 358.4 g/mol
Monoisotopic mass: 358.17802393

Overview

21-dehydrocortisone is a C21-steroid that is cortisone in which the 21-hydroxy group has been oxidised to the corresponding aldehyde. It is a steroid aldehyde, a tertiary alpha-hydroxy ketone, a 17alpha-hydroxy steroid, a 20-oxo steroid, a 21-oxo steroid, an 11-oxo steroid, a 3-oxo-Delta(4) steroid and a C21-steroid. It is functionally related to a progesterone. It derives from a hydride of a 5alpha-pregnane.

Names & identifiers

Preferred name: 21-Dehydrocortisone
IUPAC: 2-[(8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoacetaldehyde
English name: Pregn-4-en-21-al,17-hydroxy-3,11,20-trioxo- (6CI,7CI,8CI,9CI)
Molecular formula: C21H26O5
Molecular weight: 358.42814

Names & synonyms

21-dehydrocortisoneCHEBI:78596RefChem:106491416574-04-2NSC32323717-hydroxy-3,11,20-trioxopregn-4-en-21-al2-[(8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoacetaldehyde21-Dehydro-CortisoneDTXSID80317966NSC-323237Pregn-4-en-21-al,11,20-trioxo-4-pregnen-17alpha-ol-3,11,20-trione-21-al

Show more names

Pregn-4-en-21-al,17-hydroxy-3,11,20-trioxo- (6CI,7CI,8CI,9CI)

17alpha-hydroxypregn-4-en-3,11,20-trione-21-alQ27147862

Database identifiers

CAS: 16574-04-2
PubChem CID: 331383
DTXSID: DTXSID80317966

Properties

Computed structural properties

XLogP: 1.8
Topological polar surface area: 88.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 26
Formal charge: 0
Complexity: 752

Chemistry & industry

Additional notes · 1 item

DefinitionChEBI: 21-dehydrocortisone is a C21-steroid that is cortisone in which the 21-hydroxy group has been oxidised to the corresponding aldehyde. It is a 21-oxo steroid, a 17alpha-hydroxy steroid, a 20-oxo steroid, a 3-oxo-Delta(4) steroid, a C21-steroid, an 11-oxo steroid, a steroid aldehyde and a tertiary alpha-hydroxy ketone. It is functionally related to a progesterone. It derives from a hydride of a 5alpha-pregnane.

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