| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:25:55 UTC |
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| Update Date | 2020-05-07 14:45:06 UTC |
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| BMDB ID | BMDB0006773 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 11b-Hydroxyandrost-4-ene-3,17-dione |
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| Description | 11b-Hydroxyandrost-4-ene-3,17-dione is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 11b-Hydroxyandrost-4-ene-3,17-dione participates in a number of enzymatic reactions, within cattle. In particular, 11b-Hydroxyandrost-4-ene-3,17-dione can be biosynthesized from androstenedione; which is mediated by the enzyme cytochrome P450 11B1. In addition, 11b-Hydroxyandrost-4-ene-3,17-dione can be converted into adrenosterone; which is catalyzed by the enzyme corticosteroid 11-beta-dehydrogenase isozyme 1. In cattle, 11b-hydroxyandrost-4-ene-3,17-dione is involved in the metabolic pathway called the androstenedione metabolism pathway. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 11 beta-Hydroxyandrostenedione | MeSH | | 11-Hydroxy-4-androstene-3,17-dione | MeSH | | 11-Hydroxyandrostenedione, (11beta)-isomer | MeSH | | 11-Hydroxyandrostenedione, (11alpha)-isomer | MeSH | | 11-Hydroxyandrostenedione, (9beta,10alpha,11alpha)-isomer | MeSH | | 11-Hydroxyandrostenedione, (9beta,10alpha,11beta)-isomer | MeSH |
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| Chemical Formula | C19H26O3 |
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| Average Molecular Weight | 302.414 |
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| Monoisotopic Molecular Weight | 302.188194697 |
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| IUPAC Name | (1S,2R,10S,11S,15S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione |
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| Traditional Name | (1S,2R,10S,11S,15S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]12CCC(=O)[C@@]1(C)CC([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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| InChI Identifier | InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15?,17+,18-,19-/m0/s1 |
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| InChI Key | WSCUHXPGYUMQEX-CRIVMUBDSA-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
- 11-hydroxysteroid
- Oxosteroid
- 17-oxosteroid
- Hydroxysteroid
- 3-oxosteroid
- 3-oxo-delta-4-steroid
- Delta-4-steroid
- Cyclohexenone
- Cyclic alcohol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Status | Detected but not 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
- Membrane
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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 | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| General References | - Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]
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