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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
  • Animalia
  • 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
    logP10(3.4) g/LALOGPS
    logP10(3.97) g/LChemAxon
    logS10(-4.6) g/LALOGPS
    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 ]