Record Information
Version1.0
Creation date2011-09-21 00:26:36 UTC
Update date2015-07-21 06:57:35 UTC
Primary IDFDB023228
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAndrost-5-ene-3beta,17beta-diol
DescriptionAndrostenediol is a term used to refer to two different steroids with molecular weights of 290.44: '4-androstenediol' (4-androstene-3beta,17beta-diol) and '5-androstenediol' (5-androstene-3beta,17beta-diol). 4-Androstenediol is closer to testosterone structurally, and has androgenic effects. 5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Coffey, 1988). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune(HE2100). An intermediate in testosterone biosynthesis, found in the testis or the adrenal. Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-fydroxysteroid dehydrogenaseS), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-fydroxysteroid dehydrogenase). [HMDB]
CAS Number521-17-5
Structure
Thumb
Synonyms
SynonymSource
(3beta,17beta)-Androst-5-ene-3,17-diolChEBI
3beta,17beta-Dihydroxy-5-androsteneChEBI
3beta,17beta-Dihydroxyandrost-5-eneChEBI
Androst-5-en-3beta,17beta-diolChEBI
Androst-5-enediolChEBI
AndrostenediolChEBI
HermaphrodiolChEBI
TetrabolKegg
Androst-5-ene-3beta,17beta-diolKegg
(3b,17b)-Androst-5-ene-3,17-diolGenerator
(3Β,17β)-androst-5-ene-3,17-diolGenerator
3b,17b-Dihydroxy-5-androsteneGenerator
3Β,17β-dihydroxy-5-androsteneGenerator
3b,17b-Dihydroxyandrost-5-eneGenerator
3Β,17β-dihydroxyandrost-5-eneGenerator
Androst-5-en-3b,17b-diolGenerator
Androst-5-en-3β,17β-diolGenerator
Androst-5-ene-3b,17b-diolGenerator
Androst-5-ene-3β,17β-diolGenerator
Androst-5-ene-3,17-diolHMDB
b,17b-DiolHMDB
delta-5-AndrostenediolHMDB
Delta5-AndrostenediolHMDB
5 Androstene 3,17 diolHMDB
Delta 5-AndrostenediolHMDB
Parke davis brand OF androstenediolHMDB
delta 5-Androstene-3 beta,17 beta-diolHMDB
5 Androstene 3beta 17beta diolHMDB
Androst 5 ene 3 beta,17 beta diolHMDB
Androst-5-ene-3 beta,17 beta-diolHMDB
5-Androstene-3beta-17beta-diolHMDB
BisexovisterHMDB
Delta 5 AndrostenediolHMDB
5-Androstene-3,17-diolHMDB
Androst 5 ene 3,17 diolHMDB
delta 5 Androstene 3 beta,17 beta diolHMDB
(3β,17β)-androst-5-ene-3,17-diolGenerator
3β,17β-dihydroxy-5-androsteneGenerator
3β,17β-dihydroxyandrost-5-eneGenerator
5-Androstenediolhmdb
androst-5-ene-3,17-diolhmdb
b,17b-diolhmdb
delta(sup 5)-Androstenediolhmdb
delta5-Androstenediolhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP3.42ALOGPS
logP2.8ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.48 m³·mol⁻¹ChemAxon
Polarizability34.68 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H30O2
IUPAC name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol
InChI IdentifierInChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyQADHLRWLCPCEKT-LOVVWNRFSA-N
Isomeric SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
Classification
Description belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004l-3920000000-6d05021a14366bfd40baView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3920000000-6d05021a14366bfd40baView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0190000000-3ceb1bf6f3d53ee5d7e5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-2126900000-1bc7293586fc53c1c457View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-551d3445a2c6cdfa61eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0390000000-5cfc4d0f79fea1c885b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02bf-3890000000-e55a0a62bc36fe9049ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-d1deb080063b126f79ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0090000000-4d0bb4d4f197bc1e6846View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-1190000000-3f4cb9035ceae26a4876View in MoNA
ChemSpider ID10188
ChEMBL IDCHEMBL440283
KEGG Compound IDC04295
Pubchem Compound ID10634
Pubchem Substance IDNot Available
ChEBI ID2710
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03818
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDB81
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAndrostenediol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
3-oxo-5-alpha-steroid 4-dehydrogenase 1SRD5A1P18405
Testosterone 17-beta-dehydrogenase 3HSD17B3P37058
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference