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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:19:01 UTC |
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Update Date | 2020-06-04 23:01:42 UTC |
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BMDB ID | BMDB0000053 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Androstenedione |
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Description | Androstenedione, also known as fecundin, 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, androstenedione is considered to be a steroid lipid molecule. Androstenedione exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Androstenedione exists in all living organisms, ranging from bacteria to humans. Androstenedione participates in a number of enzymatic reactions, within cattle. In particular, Androstenedione can be converted into androstanedione through its interaction with the enzyme 3-oxo-5-alpha-steroid 4-dehydrogenase 1. In addition, Androstenedione can be converted into 19-hydroxyandrost-4-ene-3,17-dione through the action of the enzyme cytochrome P450 19A1. In cattle, androstenedione is involved in the metabolic pathway called the androstenedione metabolism pathway. Androstenedione is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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4-Androstene-3,17-dione | ChEBI | 4-ANDROSTENE-3-17-dione | ChEBI | delta(4)-Androsten-3,17-dione | ChEBI | delta(4)-Androstene-3,17-dione | ChEBI | Δ(4)-Androsten-3,17-dione | Generator | Δ(4)-Androstene-3,17-dione | Generator | (4)-Androsten-3,17-dione | HMDB | 17-Ketotestosterone | HMDB | 3,17-Dioxoandrost-4-ene | HMDB | 4-Androsten-3,17-dione | HMDB | 4-Androstenedione | HMDB | Androst-4-ene-3,17-dione | HMDB, KEGG | Androstendione | HMDB | D4-Androstene-3,17-dione | HMDB | delta4-Androstenedione | HMDB | Fecundin | HMDB | delta 4 Androstenedione | MeSH, HMDB | delta-4-Androstenedione | MeSH, HMDB | 4 Androstene 3,17 dione | MeSH, HMDB | Androstenedione | HMDB | delta4-Androstene-3,17-dione | HMDB | Δ4-Androstene-3,17-dione | HMDB |
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Chemical Formula | C19H26O2 |
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Average Molecular Weight | 286.4085 |
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Monoisotopic Molecular Weight | 286.193280076 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 63-05-8 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/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 |
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InChI Key | AEMFNILZOJDQLW-QAGGRKNESA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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Substituents | - Androgen-skeleton
- Oxosteroid
- 17-oxosteroid
- 3-oxosteroid
- 3-oxo-delta-4-steroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
- Mitochondria
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 170 - 173 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0578 mg/mL | Not Available | LogP | 2.75 | HANSCH,C ET AL. (1995) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
- Mitochondria
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Biospecimen Locations | - Adipose Tissue
- Adrenal Cortex
- Adrenal Gland
- Blood
- Epidermis
- Fibroblasts
- Kidney
- Liver
- Milk
- Ovary
- Placenta
- Prostate Tissue
- Skeletal Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adrenal Cortex | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adrenal Gland | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | <0.000545 uM | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00186 +/- 0.000354 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00103 +/- 0.000302 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00326 +/- 0.000946 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00147 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00101 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 0.00306 uM | Not Specified | Not Specified | Normal | | details | Ovary | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | <0.000545 uM | Not Specified | Not Specified | Treated with estradiol benzoate and progesterone | | details | Blood | Detected and Quantified | 0.000716 uM | Not Specified | Not Specified | Treated with estradiol benzoate | | details |
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External Links |
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HMDB ID | HMDB0000053 |
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DrugBank ID | DB01536 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB030678 |
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KNApSAcK ID | C00003644 |
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Chemspider ID | 5898 |
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KEGG Compound ID | C00280 |
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BioCyc ID | ANDROST4ENE |
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BiGG ID | 2210012 |
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Wikipedia Link | Androstenedione |
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METLIN ID | 2795 |
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PubChem Compound | 6128 |
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PDB ID | Not Available |
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ChEBI ID | 16422 |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
- Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]
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