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Showing metabocard for 17a,20a-Dihydroxycholesterol (HMDB0006764)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-06 15:56:24 UTC
Update Date2020-02-26 21:26:44 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
MOLSDFPDBSMILESInChI
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0054 g/LALOGPS
logP5.05ALOGPS
logP4.87ChemAxon
logS-4.9ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uel-2239400000-41515f4297af4971a848Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-2011249000-a657d6ae561e24b74e38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0003900000-f535ba20543aafa8bd7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl9-9048500000-57767148817dd16563d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-9125000000-7949d9d82d4f9d3b2002Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002900000-95b5f04d6c6ec228cfafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014s-2485900000-cd3f9e369ac3a24ebfe1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-1194100000-2d013ecd999936b89e11Spectrum
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
FoodDB 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cholesterol side-chain cleavage enzyme, mitochondrial
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
Enzyme Details
2. Steroid 17-alpha-hydroxylase/17,20 lyase
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