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Bovine Metabolome Database



Showing metabocard for Androstenedione (BMDB00053)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-31 10:18:20
Accession Number BMDB00053
Common Name Androstenedione
Description A delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma, and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while production of gonadal androstenedione is under control by gonadotropins.
Synonyms
  1. (4)-Androsten-3,17-dione
  2. 17-Ketotestosterone
  3. 3,17-Dioxoandrost-4-ene
  4. 4-Androsten-3,17-dione
  5. 4-Androstene-3,17-dione
  6. 4-androstenedione
  7. delta4-androstenedione
  8. Androst-4-ene-3,17-dione
  9. Androstenedione
  10. androstendione
  11. D4-Androstene-3,17-dione
  12. Fecundin
  13. [4-14C]-androstenedione
  14. [4-14C]androst-4-ene-3,17-dione
Chemical IUPAC Name 10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
Chemical Formula C19H26O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian_Metabolite
Species
  • ketone; alkene
Biofunction
  • Hormones, Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 286.409
Monoisotopic Molecular Weight 286.193268
Isomeric SMILES C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CCC2=O
Canonical SMILES CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC2=O
KEGG Compound ID C00280 Link Image
BioCyc ID ANDROST4ENE Link Image
BiGG ID 2210012 Link Image
Wikipedia Link Androstenedione Link Image
METLIN ID 2795 Link Image
PubChem Compound 6128 Link Image
PubChem Substance 7885977 Link Image
ChEBI ID 16422 Link Image
CAS Registry Number 63-05-8
InChI Identifier InChI=1/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
Synthesis Reference Egorova, Olga V.; Gulevskaya, Seraphima A.; Puntus, Irina F.; Filonov, Andrey E.; Donova, Marina V. Production of androstenedione using mutants of Mycobacterium sp. Journal of Chemical Technology and Biotechnology (2002), 77(2), 141-147.
Melting Point (Experimental) 170-173 oC
Experimental Water Solubility 0.0578 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 0.027 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity 2.75 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 2.93 [Predicted by ALOGPS]; 3 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
  • Cytoplasm
  • endoplasmic reticulum
Biofluid Location
  • Breast_Milk
Tissue Location
Tissue References
Adipose Tissue
Adrenal Cortex
Adrenal Gland
Fibroblasts
Gonads
Kidney
Liver
Muscle
Placenta
Prostate
Skin
Testes
Concentrations (Normal)
Biofluid Breast_Milk
Value 0.00326 +/- 0.000946 uM
Age N/A
Sex N/A
Condition Normal
Comments Whole, commercial.
References
Biofluid Breast_Milk
Value 0.00186 +/- 0.000354 uM
Age N/A
Sex N/A
Condition Normal
Comments Half-skimmed, commercial.
References
Biofluid Breast_Milk
Value 0.00103 +/- 0.000302 uM
Age N/A
Sex N/A
Condition Normal
Comments Skimmed, commercial.
References
Biofluid Breast_Milk
Value 0.00306 uM
Age N/A
Sex N/A
Condition Normal
Comments Whole milk.
References
Biofluid Breast_Milk
Value 0.00147 uM
Age N/A
Sex N/A
Condition Normal
Comments Half-skimmed.
References
Biofluid Breast_Milk
Value 0.00101 uM
Age N/A
Sex N/A
Condition Normal
Comments Skimmed.
References
Concentrations (Abnormal) Not Available
Pathway Names
  • Androgen and Estrogen Metabolism
HMDB Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
KEGG Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
SimCell Pathways
Name Androgen and Estrogen Metabolism
Image Show Link Image
Graph
SBML
General References
  1. Wikipedia Link Image