Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000353
Secondary Accession Numbers
  • HMDB00353
Metabolite Identification
Common Name3b,15b,17a-Trihydroxy-pregnenone
Description3b,15b,17a-Trihydroxy-pregnenone is a major 15 beta-hydroxylated metabolite unique to the human perinatal period. (PMID 8750436 ). The chemical synthesis of 15β-hydroxylated steroids is for use in the (a) development of new immunoassay techniques for application to newborn screening programs and fetal well-being; (b) development of new anti-androgenic drugs; and (c) study of androgen/estrogen interaction in late pregnancy.
Structure
Data?1582752125
Synonyms
ValueSource
3 beta,15 beta,17 alpha-Trihydroxy-5-pregnen-20-oneMeSH
(3beta,15beta)3,15,17-Trihydroxy-pregn-5-en-20-oneHMDB
3b,15b,17a-Trihydroxy-5-pregnen-20-oneHMDB
3beta,15beta,17alpha-Trihydroxy-5-pregnen-20-oneHMDB
Chemical FormulaC21H32O4
Average Molecular Weight348.4764
Monoisotopic Molecular Weight348.230059512
IUPAC Name(1S,2S,10R,11S,12R,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one
Traditional Name(1S,2S,10R,11S,12R,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one
CAS Registry Number80380-40-1
SMILES
[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C
InChI Identifier
InChI=1S/C21H32O4/c1-4-21(25)11-16(23)18-14-6-5-12-9-13(22)10-17(24)20(12,3)15(14)7-8-19(18,21)2/h10,12,14-16,18,22-23,25H,4-9,11H2,1-3H3/t12?,14-,15+,16-,18-,19+,20+,21-/m1/s1
InChI KeyYXMCPINQJVUPGV-HETPMVKVSA-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-oxosteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • Delta-5-steroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Ketone
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030140 )
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 Solubility0.15 g/LALOGPS
logP2.27ALOGPS
logP2.52ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.75ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity97.51 m³·mol⁻¹ChemAxon
Polarizability39.74 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+186.96532859911
AllCCS[M-H]-191.13132859911
DeepCCS[M-2H]-216.91630932474
DeepCCS[M+Na]+191.70830932474
AllCCS[M+H]+187.032859911
AllCCS[M+H-H2O]+184.332859911
AllCCS[M+NH4]+189.432859911
AllCCS[M+Na]+190.232859911
AllCCS[M-H]-191.132859911
AllCCS[M+Na-2H]-191.632859911
AllCCS[M+HCOO]-192.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3b,15b,17a-Trihydroxy-pregnenone[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C3506.1Standard polar33892256
3b,15b,17a-Trihydroxy-pregnenone[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C2887.7Standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C3231.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3b,15b,17a-Trihydroxy-pregnenone,1TMS,isomer #1CC[C@@]1(O)C[C@@H](O[Si](C)(C)C)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3032.8Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,1TMS,isomer #2CC[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3053.7Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,1TMS,isomer #3CC[C@@]1(O)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3081.7Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,2TMS,isomer #1CC[C@@]1(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3014.1Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,2TMS,isomer #2CC[C@@]1(O)C[C@@H](O[Si](C)(C)C)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3008.4Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,2TMS,isomer #3CC[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3052.5Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,3TMS,isomer #1CC[C@@]1(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3009.7Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,1TBDMS,isomer #1CC[C@@]1(O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3273.0Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,1TBDMS,isomer #2CC[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3293.0Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,1TBDMS,isomer #3CC[C@@]1(O)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3297.8Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,2TBDMS,isomer #1CC[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3470.3Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,2TBDMS,isomer #2CC[C@@]1(O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3438.0Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,2TBDMS,isomer #3CC[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3485.0Semi standard non polar33892256
3b,15b,17a-Trihydroxy-pregnenone,3TBDMS,isomer #1CC[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C3636.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pc0-1379000000-4fda3117bd2a305439022017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (3 TMS) - 70eV, Positivesplash10-0f72-1003390000-9df556b4de735cd61cab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 10V, Positive-QTOFsplash10-01q9-0009000000-10a1dfe2e84fcfd5c4732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 20V, Positive-QTOFsplash10-01pk-0169000000-661db42ac36a91f59d812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 40V, Positive-QTOFsplash10-08mr-1791000000-e3973b00ae9e66e660892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 10V, Negative-QTOFsplash10-0002-0009000000-100b460713f046c8f5b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 20V, Negative-QTOFsplash10-004j-0019000000-498b06b4d446462cb0692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 40V, Negative-QTOFsplash10-0kc2-2198000000-113e6dfe5d58729f45462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 10V, Positive-QTOFsplash10-0002-0009000000-3c6e240d9bc66c6c93742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 20V, Positive-QTOFsplash10-03ea-1229000000-315820479cd99f2a51742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 40V, Positive-QTOFsplash10-00fr-0690000000-ba831c278d3e46642e9f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 10V, Negative-QTOFsplash10-0002-0009000000-7a1691459f834500eb022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 20V, Negative-QTOFsplash10-002b-0009000000-f12a6db5f5c4c63fc7092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 40V, Negative-QTOFsplash10-0w2a-0029000000-fe86834a83d0507e779b2021-09-24Wishart 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID117725
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound133455
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceJoannou, George E.; Reeder, Anthony Y. 15b-Hydroxysteroids. (Part V). Steroids of the human perinatal period: the synthesis of 3b,15b,17a-trihydroxy-5-pregnen-20-one from 15b,17a-dihydroxy-4-pregnen-3,20-dione. Steroids (1996), 61(1), 18-21.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Reeder AY, Joannou GE: 15 beta-hydroxysteroids (part I). Steroids of the human perinatal period: the synthesis of 3 beta,15 beta, 17 alpha-trihydroxy-5-pregnen-20-one. Steroids. 1996 Feb;61(2):74-81. [PubMed:8750436 ]
  2. Joannou GE: Identification of 15 beta-hydroxylated C21 steroids in the neo-natal period: the role of 3 alpha,15 beta,17 alpha-trihydroxy-5 beta-pregnan-20-one in the perinatal diagnosis of congenital adrenal hyperplasia (CAH) due to a 21-hydroxylase deficiency. J Steroid Biochem. 1981 Sep;14(9):901-12. [PubMed:6975400 ]
  3. Joannou GE, Reeder AY: 15 beta-hydroxysteroids (Part V). Steroids of the human perinatal period: the synthesis of 3 beta, 15 beta, 17 alpha-trihydroxy-5-pregnen-20-one from 15 beta, 17 alpha-dihydroxy-4-pregnen-3,20-dione. Steroids. 1996 Jan;61(1):18-21. [PubMed:8789731 ]
  4. Joannou GE, Reeder AY: 15 beta-hydroxysteroids (part II). Steroids of the human perinatal period: the synthesis of 3 alpha,15 beta, 17 alpha-trihydroxy-5 beta-pregnan-20-one. Steroids. 1996 Feb;61(2):82-8. [PubMed:8750437 ]
  5. Joannou GE, Reeder AY: 15 beta-hydroxysteroids (Part III). Steroids of the human perinatal period: the synthesis of 3 beta, 15 beta, 17 alpha-trihydroxy-5-pregnen-20-one. Application of n-butyl boronic acid protection of a 17,20-glycol. Steroids. 1996 Jan;61(1):11-7. [PubMed:8789730 ]