Hydrocortisone 17-butyrate (CHEM018627)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:24:26 UTC
Update Date2016-11-09 01:15:50 UTC
Accession NumberCHEM018627
Identification
Common NameHydrocortisone 17-butyrate
ClassSmall Molecule
DescriptionCortisol esterified with butyric acid at the 17-hydroxy group.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11beta,21-Dihydroxy-17alpha-butyryloxy-4-pregnene-3,20-dioneChEBI
17-O-ButyrylcortisolChEBI
H-17-bChEBI
Hydrocortisone 17-butyrateChEBI
Hydrocortisone butyrateChEBI
Hydrocortisone-17alpha-butyrateChEBI
LocoidKegg
11b,21-Dihydroxy-17a-butyryloxy-4-pregnene-3,20-dioneGenerator
11Β,21-dihydroxy-17α-butyryloxy-4-pregnene-3,20-dioneGenerator
Hydrocortisone 17-butyric acidGenerator
Hydrocortisone butyric acidGenerator
Hydrocortisone-17a-butyrateGenerator
Hydrocortisone-17a-butyric acidGenerator
Hydrocortisone-17alpha-butyric acidGenerator
Hydrocortisone-17α-butyrateGenerator
Hydrocortisone-17α-butyric acidGenerator
Cortisol 17-butyric acidGenerator
Hydrocortisone-17-butyrateMeSH
[(8S,9S,10R,11S,13S,14S,17R)-11-Hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] butanoic acidGenerator
Cortisol 17-butyrateMeSH
Chemical FormulaC25H36O6
Average Molecular Mass432.557 g/mol
Monoisotopic Mass432.251 g/mol
CAS Registry Number13609-67-1
IUPAC Name(1S,2R,10S,11S,14R,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl butanoate
Traditional Namehydrocortisone 17-butyrate
SMILES[H][C@@]12CC[C@](OC(=O)CCC)(C(=O)CO)[C@@]1(C)C[C@]([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C25H36O6/c1-4-5-21(30)31-25(20(29)14-26)11-9-18-17-7-6-15-12-16(27)8-10-23(15,2)22(17)19(28)13-24(18,25)3/h12,17-19,22,26,28H,4-11,13-14H2,1-3H3/t17-,18-,19-,22+,23-,24-,25-/m0/s1
InChI KeyBMCQMVFGOVHVNG-TUFAYURCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • Pregnane-skeleton
  • Steroid ester
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-acyloxy ketone
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.21ALOGPS
logP2.86ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.75ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity115.78 m³·mol⁻¹ChemAxon
Polarizability47.79 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-5911100000-e8864e9205adebf34b2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-2940000000-731a77b68084064be8edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015a-3006900000-f18ee73bc0a7d3c13043Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-7039200000-f7cff2d74b7123f39192Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pid-3292000000-278a04cb3a54f8c484a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-3005900000-e4359c0b8ab56a4704f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03du-4009200000-8c54dec71bd1615fb256Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1003-9007000000-5a5528ba9939d962b66bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001234
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHydrocortisone-17-Butyrate
Chemspider IDNot Available
ChEBI ID31674
PubChem Compound ID26133
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16566122
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2265088
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24504495
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26085051