Showing metabocard for Allopregnanolone (BMDB0001449)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:08 UTC
Update Date2020-04-22 15:08:15 UTC
BMDB IDBMDB0001449
Secondary Accession Numbers
  • BMDB01449
Metabolite Identification
Common NameAllopregnanolone
DescriptionAllopregnanolone, also known as 3alpha-OH DHP or 3alpha,5alpha-THP, 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. Thus, allopregnanolone is considered to be a steroid lipid molecule. Allopregnanolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3alpha,5alpha)-3-Hydroxypregnan-20-oneChEBI
3alpha,5alpha-TetrahydroprogesteroneChEBI
3alpha,5alpha-THPChEBI
3alpha-Hydroxy-5alpha-dihydroprogesteroneChEBI
3alpha-Hydroxy-5alpha-pregnan-20-oneChEBI
3alpha-OH DHPChEBI
5alpha-Pregnan-3alpha-ol-20-oneChEBI
Allopregnan-3alpha-ol-20-oneChEBI
AllotetrahydroprogesteroneChEBI
BrexanolonaChEBI
BrexanolonumChEBI
SAGE-547ChEBI
SGE-102ChEBI
ZulressoChEBI
(3a,5a)-3-Hydroxypregnan-20-oneGenerator
(3Α,5α)-3-hydroxypregnan-20-oneGenerator
3a,5a-TetrahydroprogesteroneGenerator
3Α,5α-tetrahydroprogesteroneGenerator
3a,5a-THPGenerator
3Α,5α-THPGenerator
3a-Hydroxy-5a-dihydroprogesteroneGenerator
3Α-hydroxy-5α-dihydroprogesteroneGenerator
3a-Hydroxy-5a-pregnan-20-oneGenerator
3Α-hydroxy-5α-pregnan-20-oneGenerator
3a-OH DHPGenerator
3Α-OH DHPGenerator
5a-Pregnan-3a-ol-20-oneGenerator
5Α-pregnan-3α-ol-20-oneGenerator
Allopregnan-3a-ol-20-oneGenerator
Allopregnan-3α-ol-20-oneGenerator
(+)-3a-Hydroxy-5a-pregnan-20-oneHMDB
(3a)-AllopregnanoloneHMDB
3-a-TetrahydroprogesteroneHMDB
3-alpha-TetrahydroprogesteroneHMDB
3a,5a-PregnanoloneHMDB
3a-Hydroxy-5a-pregnane-20-oneHMDB
5a-Pregnane-3a-ol-20-oneHMDB
3-Hydroxypregnan-20-oneHMDB
alpha-Hydroxy-5 alpha-pregnan-20-one, 3HMDB
Pregnan-3alpha-ol-20-oneHMDB
Pregnanolone, (3alpha)-isomerHMDB
3 Hydroxypregnan 20 oneHMDB
3 alpha Hydroxy 5 alpha pregnan 20 oneHMDB
3 alpha-Hydroxy-5 alpha-pregnan-20-oneHMDB
Pregnan 3alpha ol 20 oneHMDB
alpha-Pregnan-20-one, 3 alpha-hydroxy-5HMDB
(+)-3alpha-Hydroxy-5alpha-pregnan-20-oneHMDB
(+)-3Α-hydroxy-5α-pregnan-20-oneHMDB
(3alpha)-AllopregnanoloneHMDB
(3Α)-allopregnanoloneHMDB
3alpha,5alpha-PregnanoloneHMDB
3alpha-Hydroxy-5alpha-pregnane-20-oneHMDB
3Α,5α-pregnanoloneHMDB
3Α-hydroxy-5α-pregnane-20-oneHMDB
5alpha-Pregnane-3alpha-ol-20-oneHMDB
5Α-pregnane-3α-ol-20-oneHMDB
AllopregnanoloneMeSH, ChEBI
Chemical FormulaC21H34O2
Average Molecular Weight318.4935
Monoisotopic Molecular Weight318.255880332
IUPAC Name1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one
Traditional Name1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone
CAS Registry Number516-54-1
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O
InChI Identifier
InChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyAURFZBICLPNKBZ-SYBPFIFISA-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-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 3-hydroxy-5alpha-pregnan-20-one (CHEBI:50169 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030156 )
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point177 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.28ALOGPS
logP3.99ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability38.52 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0udi-6910000000-837b37f206729753b640View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-6910000000-837b37f206729753b640View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1174-0292000000-fb2c0f3a1cfddb10cb08View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2139000000-ab8a6de8f5a129af086eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0129000000-90e5fcb36022dd1ba688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0396000000-4c39fe7ccd8e0c86e179View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2490000000-7ac55935cc0d4da95860View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-fa09e69c9c0b6736d2e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0069000000-d1d57e3e1a99da4ed11fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-1193000000-44d1597a59ac11f16a41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-5b53b3ba37ccafca449fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lgi-1797000000-c11629ffa10cac4be118View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-8910000000-2813a600e98ff5997275View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-bbaa566ea695ae62f84eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0029000000-ac1c6a15538469151b6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ks-0093000000-db70f670eb2440b743f9View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001449
DrugBank IDDB11859
Phenol Explorer Compound IDNot Available
FooDB IDFDB022630
KNApSAcK IDNot Available
Chemspider ID83760
KEGG Compound IDC13712
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllopregnanolone
METLIN IDNot Available
PubChem Compound92786
PDB IDNot Available
ChEBI ID50169
References
Synthesis ReferenceWiebe, J. P.; Deline, C.; Buckingham, K. D.; Dave, Vinod; Stothers, J. B. Synthesis of the allylic gonadal steroids, 3a-hydroxy-4-pregnen-20-one and 3a-hydroxy-4-androsten-17-one, and of 3a-hydroxy-5a-pregnan-20-one. Steroids (1985), 45(1), 39-51.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available