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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-10-05 13:38:29 UTC
Update Date2022-03-07 02:51:28 UTC
HMDB IDHMDB0013121
Secondary Accession Numbers
  • HMDB13121
Metabolite Identification
Common Name7-Dehydropregnenolone
Description7-Dehydropregnenolone is a 21-carbon steroid, derived from cholesterol and found in steroid hormone-producing tissues. It is the precursor to Gonadal steroid hormones and the adrenal corticosteroid. 7-Dehydropregnenolone is the the single product of metabolism of 7-dehydrocholesterol by CYP11A1 (PMID 14657394 ).
Structure
Data?1582753095
Synonyms
ValueSource
7-DHPHMDB
7-DehydropregnenoloneMeSH
Chemical FormulaC21H30O2
Average Molecular Weight314.4617
Monoisotopic Molecular Weight314.224580204
IUPAC Name1-[(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-14-yl]ethan-1-one
Traditional Name1-[(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-14-yl]ethanone
CAS Registry NumberNot Available
SMILES
CC(=O)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,15,17-19,23H,6-12H2,1-3H3/t15-,17?,18?,19?,20-,21+/m0/s1
InChI KeyQTVNPWWLYMFLEI-IOHSXPNESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct Parent20-oxosteroids
Alternative Parents
Substituents
  • 20-oxosteroid
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP4.47ALOGPS
logP3.18ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.61 m³·mol⁻¹ChemAxon
Polarizability36.81 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.96631661259
DarkChem[M-H]-166.9131661259
DeepCCS[M-2H]-211.45130932474
DeepCCS[M+Na]+186.67930932474
AllCCS[M+H]+181.232859911
AllCCS[M+H-H2O]+178.232859911
AllCCS[M+NH4]+184.032859911
AllCCS[M+Na]+184.832859911
AllCCS[M-H]-186.632859911
AllCCS[M+Na-2H]-186.932859911
AllCCS[M+HCOO]-187.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-DehydropregnenoloneCC(=O)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C3229.9Standard polar33892256
7-DehydropregnenoloneCC(=O)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C2772.5Standard non polar33892256
7-DehydropregnenoloneCC(=O)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C2812.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-Dehydropregnenolone,1TMS,isomer #1CC(=O)C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C2849.0Semi standard non polar33892256
7-Dehydropregnenolone,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C2868.8Semi standard non polar33892256
7-Dehydropregnenolone,1TMS,isomer #3C=C(O[Si](C)(C)C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C2837.2Semi standard non polar33892256
7-Dehydropregnenolone,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C2886.3Semi standard non polar33892256
7-Dehydropregnenolone,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C2838.7Standard non polar33892256
7-Dehydropregnenolone,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C3219.4Standard polar33892256
7-Dehydropregnenolone,2TMS,isomer #2C=C(O[Si](C)(C)C)C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C2852.2Semi standard non polar33892256
7-Dehydropregnenolone,2TMS,isomer #2C=C(O[Si](C)(C)C)C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C2813.0Standard non polar33892256
7-Dehydropregnenolone,2TMS,isomer #2C=C(O[Si](C)(C)C)C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C3295.7Standard polar33892256
7-Dehydropregnenolone,1TBDMS,isomer #1CC(=O)C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3111.9Semi standard non polar33892256
7-Dehydropregnenolone,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C3134.2Semi standard non polar33892256
7-Dehydropregnenolone,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C3114.7Semi standard non polar33892256
7-Dehydropregnenolone,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3394.1Semi standard non polar33892256
7-Dehydropregnenolone,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3394.6Standard non polar33892256
7-Dehydropregnenolone,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3469.1Standard polar33892256
7-Dehydropregnenolone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3356.8Semi standard non polar33892256
7-Dehydropregnenolone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3368.7Standard non polar33892256
7-Dehydropregnenolone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3522.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-Dehydropregnenolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-059g-0190000000-13dcd143f6d608f5cef62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Dehydropregnenolone GC-MS (1 TMS) - 70eV, Positivesplash10-05fu-2049000000-6fc34b27d947b847adb02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Dehydropregnenolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Dehydropregnenolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 10V, Positive-QTOFsplash10-00kb-0095000000-16f22892d4ff716f39592017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 20V, Positive-QTOFsplash10-00kb-0391000000-555fba17ef35f26f36d62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 40V, Positive-QTOFsplash10-0079-2490000000-7ebab71d232e3f6d0a192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 10V, Negative-QTOFsplash10-03di-0029000000-dcda0b7111c264418e6d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 20V, Negative-QTOFsplash10-03di-0079000000-326259d6736bb446d0cd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 40V, Negative-QTOFsplash10-0002-1090000000-a4f0bc4947785686f7e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 10V, Negative-QTOFsplash10-03di-0009000000-2514638890974c4f71f32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 20V, Negative-QTOFsplash10-03dj-0089000000-66ecd4ecd833feb178fe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 40V, Negative-QTOFsplash10-00p1-0090000000-8fb13ea7be343d3a5a422021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 10V, Positive-QTOFsplash10-014i-0069000000-c7df4adee5b340e7afef2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 20V, Positive-QTOFsplash10-0gdj-1492000000-eb316c6ad9aec6fd5b8f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Dehydropregnenolone 40V, Positive-QTOFsplash10-052f-9710000000-e26067cb15664f28558f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029294
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481610
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guryev O, Carvalho RA, Usanov S, Gilep A, Estabrook RW: A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1). Proc Natl Acad Sci U S A. 2003 Dec 9;100(25):14754-9. Epub 2003 Dec 1. [PubMed:14657394 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.