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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 21:57:25 UTC
Update Date2021-09-14 15:40:06 UTC
HMDB IDHMDB0006070
Secondary Accession Numbers
  • HMDB06070
Metabolite Identification
Common NamePregnanetriol
DescriptionPregnanetriol belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Based on a literature review a significant number of articles have been published on Pregnanetriol.
Structure
Data?1582752373
Synonyms
ValueSource
5-beta-Pregnane-3,17,20-triolHMDB
5beta-Pregnane-3alpha,17alpha,20alpha-triolHMDB
Chemical FormulaC21H36O3
Average Molecular Weight336.5087
Monoisotopic Molecular Weight336.266445018
IUPAC Name(1S,2S,5R,7R,10R,11S,14R,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional Name(1S,2S,5R,7R,10R,11S,14R,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
CAS Registry Number27178-64-9
SMILES
[H][C@@]12CC[C@](O)(C(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H36O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h13-18,22-24H,4-12H2,1-3H3/t13?,14-,15-,16-,17+,18+,19+,20+,21+/m1/s1
InChI KeySCPADBBISMMJAW-HWPIAJDMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-hydroxysteroid
  • 17-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP10(3.39) g/LALOGPS
logP10(2.85) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)13.42ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.23 m³·mol⁻¹ChemAxon
Polarizability40 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.52431661259
DarkChem[M-H]-173.71231661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pregnanetriol,1TMS,#1CC(O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C2880.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,1TMS,#2CC(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C2838.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,1TMS,#3CC(O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C2886.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,2TMS,#1CC(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C2922.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,2TMS,#2CC(O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C2886.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,2TMS,#3CC(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C2823.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,3TMS,#1CC(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C2917.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,1TBDMS,#1CC(O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3161.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,1TBDMS,#2CC(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3110.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,1TBDMS,#3CC(O)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3160.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,2TBDMS,#1CC(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3466.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,2TBDMS,#2CC(O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3415.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,2TBDMS,#3CC(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3361.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pregnanetriol,3TBDMS,#1CC(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3710.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pregnanetriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0avl-2197000000-3d4c01e2d71106de55982017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pregnanetriol GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2101590000-9e9b8814726e15c722422017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pregnanetriol 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 - Pregnanetriol 10V, Positive-QTOFsplash10-014r-0009000000-3fe8ea9477287c7e5ee22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 20V, Positive-QTOFsplash10-0gb9-0159000000-2182736ac08c8ae7ff7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 40V, Positive-QTOFsplash10-0umr-1593000000-aed32c474fb7eea14b1a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 10V, Negative-QTOFsplash10-000i-0019000000-b0671b68c591d7cbd1d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 20V, Negative-QTOFsplash10-0079-0097000000-bf3938faf2d2247f6c902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 40V, Negative-QTOFsplash10-02if-0092000000-43ec3cee5d391addca372017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 10V, Positive-QTOFsplash10-00kr-0009000000-70f09877f29160c8fb4e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 20V, Positive-QTOFsplash10-014i-0902000000-fe825f870ea28f23d9072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 40V, Positive-QTOFsplash10-00kb-4910000000-acbbeef6557af7e3812f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 10V, Negative-QTOFsplash10-000i-0009000000-2d1f27fd1f53e7ee24d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 20V, Negative-QTOFsplash10-000i-0039000000-37cb356855d962a6f8062021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanetriol 40V, Negative-QTOFsplash10-007c-0093000000-1778454aeddb068953222021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified<0.0533 umol/mmol creatinineNot SpecifiedBothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.02 umol/mmol creatinineNewborn (0-30 days old)Female11-beta-hydroxylase deficiency details
UrineDetected and Quantified0.0267-0.0733 umol/mmol creatinineChildren (1-13 years old)Both11-beta-hydroxylase deficiency details
Associated Disorders and Diseases
Disease References
11-beta-Hydroxylase deficiency
  1. Burren CP, Montalto J, Yong AB, Batch JA: CYP11 beta 1 (11-beta-hydroxylase) deficiency in congenital adrenal hyperplasia. J Paediatr Child Health. 1996 Oct;32(5):433-8. [PubMed:8933406 ]
Associated OMIM IDs
  • 202010 (11-beta-Hydroxylase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023826
KNApSAcK IDNot Available
Chemspider ID2297709
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPregnanetriol
METLIN IDNot Available
PubChem Compound3032833
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029963
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.