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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:37 UTC
NP-MRD IDNP0001267
Secondary Accession NumbersNone
Natural Product Identification
Common NameAndrostanedione
DescriptionAndrostanedione 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. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
5alpha-Androstan-3,17-dioneChEBI
5a-Androstan-3,17-dioneGenerator
5Α-androstan-3,17-dioneGenerator
(5a)-Androstane-3,17-dioneHMDB
5-alpha-Androstane-3,17-dioneHMDB
5a-Androsta-3,17-dioneHMDB
5a-Androstane-3, 17-dioneHMDB
5a-Androstane-3,17-dioneHMDB
5a-AndrostanedioneHMDB
5alpha-Androstane-3,17-dioneHMDB
Androstane-3,17-dioneHMDB
Androstane-3,7-dioneHMDB
Androstane-3,17-dione, (2-3(H)-labeled, (2beta,5beta))-isomerHMDB
Androstane-3,17-dione, (4-(3)H-labeled, (4alpha,5beta))-isomerHMDB
Androstane-3,17-dione, (2-3(H)-labeled, (2alpha,5beta))-isomerHMDB
Androstane-3,17-dione, (4-(3)H-labeled, (4beta,5beta))-isomerHMDB
Androstane-3,17-dione, (5beta)-isomerHMDB
3,17-Dioxy-5 alpha-androstaneHMDB
5 alpha-AndrostanedioneHMDB
5 beta-Androstane-3,17-dioneHMDB
5 alpha-Androstane-3,17-dioneHMDB
Androstane-3,17-dione, (5alpha)-isomerHMDB
Chemical FormulaC19H28O2
Average Mass288.4244 Da
Monoisotopic Mass288.20893 Da
IUPAC Name(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione
Traditional Name(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione
CAS Registry Number846-46-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1
InChI KeyRAJWOBJTTGJROA-WZNAKSSCSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
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
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133.5 - 134.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0074 g/LALOGPS
logP3.4ALOGPS
logP3.97ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.78ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.78 m³·mol⁻¹ChemAxon
Polarizability33.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000899
DrugBank IDDB01561
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022307
KNApSAcK IDNot Available
Chemspider ID193520
KEGG Compound IDC00674
BioCyc IDCPD-342
BiGG ID42505
Wikipedia LinkAndrostanedione
METLIN ID5855
PubChem Compound222865
PDB IDNot Available
ChEBI ID15994
Good Scents IDNot Available
References
General References
  1. Karlsson T, Vahlquist A, Kedishvili N, Torma H: 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochem Biophys Res Commun. 2003 Mar 28;303(1):273-8. [PubMed:12646198 ]
  2. Gonzalez-Santos MR, Gaja-Rodriguez OV, Alonso-Uriarte R, Sojo-Aranda I, Cortes-Gallegos V: Sleep deprivation and adaptive hormonal responses of healthy men. Arch Androl. 1989;22(3):203-7. [PubMed:2757458 ]
  3. Sharifi N: The 5alpha-androstanedione pathway to dihydrotestosterone in castration-resistant prostate cancer. J Investig Med. 2012 Feb;60(2):504-7. doi: 10.2310/JIM.0b013e31823874a4. [PubMed:22064602 ]
  4. Milewich L, Kaimal V, Shaw CB, Johnson AR: Androstenedione metabolism in human lung fibroblasts. J Steroid Biochem. 1986 Apr;24(4):893-7. doi: 10.1016/0022-4731(86)90451-6. [PubMed:3702464 ]
  5. Howell S, Song W, Pastuszak A, Khera M: Differential Gene Expression in Post-Finasteride Syndrome Patients. J Sex Med. 2021 Sep;18(9):1479-1490. doi: 10.1016/j.jsxm.2021.05.009. Epub 2021 Jul 8. [PubMed:34247957 ]