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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:06 UTC
HMDB IDHMDB0000921
Secondary Accession Numbers
  • HMDB00921
Metabolite Identification
Common NameCholestenone
DescriptionCholestenone belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, cholestenone is considered to be a sterol lipid molecule. Cholestenone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1582752165
Synonyms
ValueSource
4-Cholesten-3-oneChEBI
Cholest-4-en-3-oneHMDB
(17b)-17-Octylandrost-4-en-3-oneHMDB
3-Oxocholest-4-eneHMDB
D4-Cholesten-3-oneHMDB
D4-CholestenoneHMDB
(+)-4-Cholesten-3-oneHMDB
(17beta)-17-Octylandrost-4-en-3-oneHMDB
(17Β)-17-octylandrost-4-en-3-oneHMDB
4-CholestenoneHMDB
CholesteroneHMDB
delta4-Cholesten-3-oneHMDB
delta4-CholestenoneHMDB
Δ4-cholesten-3-oneHMDB
Δ4-cholestenoneHMDB
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number601-57-0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyNYOXRYYXRWJDKP-GYKMGIIDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point79 - 82 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP10(6.57) g/LALOGPS
logP10(7.68) g/LChemAxon
logS10(-7.2) g/LALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.57 m³·mol⁻¹ChemAxon
Polarizability49.79 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.01131661259
DarkChem[M-H]-192.79331661259
AllCCS[M+H]+202.87332859911
AllCCS[M-H]-203.58332859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cholestenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-06di-2229000000-cfc561b8bff8d75878192017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholestenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0009000000-3ba0c0c4f5b64032e9692012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001j-9803000000-0041fa800c684344d6f82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0532-9400000000-d0d60fb4fbca5c06cb012012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone 40V, Positive-QTOFsplash10-0a4j-7900000000-3ad74b36fc9e3f4b9db42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone 40V, Positive-QTOFsplash10-0a4j-7900000000-b5cc0e7902cd6cdf783d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone 60V, Positive-QTOFsplash10-0a4j-9700000000-d3906eae7c45c97a5b782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone 40V, Positive-QTOFsplash10-0a4j-7900000000-1fd5e37ad61a39390fab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone 60V, Positive-QTOFsplash10-0a4j-9800000000-0f1c723e5ac58579caf82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cholestenone 60V, Positive-QTOFsplash10-0a4j-9700000000-f5034b023ae3ba1d95772021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 10V, Positive-QTOFsplash10-000i-0019000000-6f526ead547a001ecc552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 20V, Positive-QTOFsplash10-0ap0-3119000000-2a830558981b265c89c02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 40V, Positive-QTOFsplash10-0aor-5239000000-c531237dfc518c04a8a72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 10V, Negative-QTOFsplash10-001i-0009000000-fe5ea0c4be8b4b64ece72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 20V, Negative-QTOFsplash10-001i-0009000000-5d059b2d1fa5085dd8b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 40V, Negative-QTOFsplash10-0ldi-2019000000-53be05d0d2e2dca6edfd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 10V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 20V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 40V, Negative-QTOFsplash10-001i-0009000000-79017ac8303e5bbe2a842021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 10V, Positive-QTOFsplash10-000i-0009000000-200e1637ea1dc1324da12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 20V, Positive-QTOFsplash10-060c-8269000000-6ca50c6965cc22bd1da82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholestenone 40V, Positive-QTOFsplash10-052f-9500000000-568f77aab2459f79ab932021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Gall Bladder
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.079 +/- 0.022 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022319
KNApSAcK IDC00036093
Chemspider ID82602
KEGG Compound IDC00599
BioCyc IDCPD-323
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3898
PubChem Compound91477
PDB IDNot Available
ChEBI ID16175
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMori, Susumu. Steroids. IX. A new synthesis of cholestenone and the addition of hypochlorous acid to cholesterol. Nippon Kagaku Kaishi (1921-47) (1952), Pure Chem. Sect. 73 547-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nguyen DH, Taub D: Cholesterol is essential for macrophage inflammatory protein 1 beta binding and conformational integrity of CC chemokine receptor 5. Blood. 2002 Jun 15;99(12):4298-306. [PubMed:12036855 ]
  2. Nguyen DH, Taub DD: Inhibition of chemokine receptor function by membrane cholesterol oxidation. Exp Cell Res. 2003 Nov 15;291(1):36-45. [PubMed:14597406 ]
  3. Norlin M, von Bahr S, Bjorkhem I, Wikvall K: On the substrate specificity of human CYP27A1: implications for bile acid and cholestanol formation. J Lipid Res. 2003 Aug;44(8):1515-22. Epub 2003 Jun 1. [PubMed:12777473 ]
  4. Maeda Y, Kamimura R, Higashi S, Namba K, Tanaka E, Iwamura T, Setoguchi T: A simple, accurate, and sensitive assay method of dehydroepiandrosterone sulfate: application for quantitative determination in human breast cyst and duct fluids. Steroids. 2002 Apr;67(5):333-8. [PubMed:11958788 ]
  5. Weststrate JA, Ayesh R, Bauer-Plank C, Drewitt PN: Safety evaluation of phytosterol esters. Part 4. Faecal concentrations of bile acids and neutral sterols in healthy normolipidaemic volunteers consuming a controlled diet either with or without a phytosterol ester-enriched margarine. Food Chem Toxicol. 1999 Nov;37(11):1063-71. [PubMed:10566877 ]
  6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
5-beta-Cholestan-3-one + NADP → Cholestenone + NADPHdetails