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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-06 15:56:24 UTC
Update Date2021-09-14 15:40:08 UTC
HMDB IDHMDB0006764
Secondary Accession Numbers
  • HMDB06764
Metabolite Identification
Common Name17a,20a-Dihydroxycholesterol
Description17alpha,21-Dihydroxypregnenolone, also known as 3β,17,21-trihydroxy-pregn-5-en-20-one, 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. Thus, 17alpha,21-dihydroxypregnenolone is considered to be a steroid lipid molecule. 17alpha,21-Dihydroxypregnenolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752404
Synonyms
ValueSource
17a,21-DihydroxypregnenoloneGenerator
17Α,21-dihydroxypregnenoloneGenerator
17alpha,21-Dihydroxypreg-nenoloneHMDB
17, 21-DihydroxypregnenoloneHMDB
3Β,17α,21-trihydroxypregnenoneHMDB
3beta,17alpha,21-TrihydroxypregnenoneHMDB
17,21-DihydroxypregnenoloneHMDB
3Β,17,21-trihydroxy-pregn-5-en-20-oneHMDB
3beta,17,21-Trihydroxy-pregn-5-en-20-oneHMDB
(3Β)-3,17,21-trihydroxypregn-5-en-20-oneHMDB
(3beta)-3,17,21-Trihydroxypregn-5-en-20-oneHMDB
3Β,17α,21-trihydroxypregn-5-en-20-oneHMDB
3beta,17alpha,21-Trihydroxypregn-5-en-20-oneHMDB
17alpha,20alpha-DihydroxycholesterolHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(2R,5S,10R,14R,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol
Traditional Name(2R,5S,10R,14R,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol
CAS Registry NumberNot Available
SMILES
[H]C12CC[C@](O)([C@](C)(O)CCCC(C)C)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O3/c1-18(2)7-6-13-26(5,29)27(30)16-12-23-21-9-8-19-17-20(28)10-14-24(19,3)22(21)11-15-25(23,27)4/h8,18,20-23,28-30H,6-7,9-17H2,1-5H3/t20-,21+,22?,23?,24-,25-,26+,27+/m0/s1
InChI KeyPRZXKPDANWDCNC-IMVKCWHASA-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
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Oxosteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

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 Solubility0.0054 g/LALOGPS
logP10(5.05) g/LALOGPS
logP10(4.87) g/LChemAxon
logS10(-4.9) g/LALOGPS
pKa (Strongest Acidic)13.25ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.6 m³·mol⁻¹ChemAxon
Polarizability50.5 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.76331661259
DarkChem[M-H]-198.91231661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17a,20a-Dihydroxycholesterol,1TMS,#1CC(C)CCC[C@@](C)(O)[C@@]1(O[Si](C)(C)C)CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3449.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,1TMS,#2CC(C)CCC[C@@](C)(O[Si](C)(C)C)[C@@]1(O)CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3416.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,1TMS,#3CC(C)CCC[C@@](C)(O)[C@@]1(O)CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C3449.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,2TMS,#1CC(C)CCC[C@@](C)(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3479.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,2TMS,#2CC(C)CCC[C@@](C)(O)[C@@]1(O[Si](C)(C)C)CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C3436.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,2TMS,#3CC(C)CCC[C@@](C)(O[Si](C)(C)C)[C@@]1(O)CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C3430.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,3TMS,#1CC(C)CCC[C@@](C)(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C3460.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,1TBDMS,#1CC(C)CCC[C@@](C)(O)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3696.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,1TBDMS,#2CC(C)CCC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3679.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,1TBDMS,#3CC(C)CCC[C@@](C)(O)[C@@]1(O)CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C3698.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,2TBDMS,#1CC(C)CCC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3976.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,2TBDMS,#2CC(C)CCC[C@@](C)(O)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C3909.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,2TBDMS,#3CC(C)CCC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C3913.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
17a,20a-Dihydroxycholesterol,3TBDMS,#1CC(C)CCC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C4165.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 17a,20a-Dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uel-2239400000-41515f4297af4971a8482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17a,20a-Dihydroxycholesterol GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-2011249000-a657d6ae561e24b74e382017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17a,20a-Dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17a,20a-Dihydroxycholesterol 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 - 17a,20a-Dihydroxycholesterol 10V, Positive-QTOFsplash10-0uxr-0003900000-f535ba20543aafa8bd7e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 20V, Positive-QTOFsplash10-0fl9-9048500000-57767148817dd16563d32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 40V, Positive-QTOFsplash10-0avi-9125000000-7949d9d82d4f9d3b20022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0002900000-95b5f04d6c6ec228cfaf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 20V, Negative-QTOFsplash10-014s-2485900000-cd3f9e369ac3a24ebfe12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 40V, Negative-QTOFsplash10-0079-1194100000-2d013ecd999936b89e112017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 10V, Positive-QTOFsplash10-0159-1115900000-d5e9dc6e8588fe35bcb92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 20V, Positive-QTOFsplash10-0901-7931100000-a6fdc1b6f1d0238eb7682021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 40V, Positive-QTOFsplash10-0006-9720000000-8e7c40e57518c7456eda2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0000900000-f2cb6399034352e924c82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 20V, Negative-QTOFsplash10-014i-0030900000-99cff478edd24aa7f1632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17a,20a-Dihydroxycholesterol 40V, Negative-QTOFsplash10-07vr-4692300000-68c60377630672ef50502021-09-24Wishart 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 IDFDB024065
KNApSAcK IDNot Available
Chemspider ID167253
KEGG Compound IDC05487
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound192735
PDB IDNot Available
ChEBI ID27832
Food Biomarker OntologyNot Available
VMH IDM00406
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
Reactions
17a,20a-Dihydroxycholesterol + Oxygen + Hydrogen Ion + Reduced adrenal ferredoxin → 17a-Hydroxypregnenolone + 4-Methylpentanal + Water + Oxidized adrenal ferredoxindetails
General function:
Involved in monooxygenase activity
Specific function:
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:
CYP17A1
Uniprot ID:
P05093
Molecular weight:
57369.995
Reactions
20alpha-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 17a,20a-Dihydroxycholesterol + NADP + Waterdetails