| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2015-10-09 22:30:52 UTC |
|---|
| Update date | 2017-01-19 02:36:25 UTC |
|---|
| FoodComEx ID | PC000480 |
|---|
| FoodDB Record | FDB022074 |
|---|
| Chemical Information |
|---|
| Name | Androstanediol |
|---|
| Description | Androstanediol is a metabolite of dihydrotestosterone, itself a metabolite of testosterone. Androstanediol is implicated in the regulation of gonadotropin secretion. As a metabolite of dihydroxytestosterone formed in the peripheral tissues, androstanediol and androstnediol-glucuronide can be used to estimate peripheral androgen activity. Androstanediol is a potential GABA (A) receptor-modulating neurosteroid with anticonvulsant properties and hence could act as a key neuromodulator in the central nervous system. It is considered that androstanediol has hedonic effects; therefore it is anticipated that androgens that are readily metabolized to androstanediol may have higher abuse potential than androgens that are not as easily metabolized to androstanediol. These results add to the growing literature indicating that athletes and non-athletes may be at considerable risk when they abuse androgens. (PMID: 11500254, 16040068, 11744084) [HMDB] |
|---|
| CAS Number | 25126-76-5 |
|---|
| Structure | |
|---|
| Synonyms | | Synonym | Source |
|---|
| 3-a-androstanediol | hmdb | | 3-alpha-androstanediol | hmdb | | 3alpha-androstanediol | hmdb | | 5 a-androstane-3 a, 17 b-diol | hmdb | | 5 alpha-androstane-3 alpha, 17 beta-diol | hmdb | | 5-a-androstane-3-a, 17-b-diol | hmdb | | 5-alpha-androstan-3-alpha,17-beta-diol | hmdb | | 5-alpha-androstane-3-a, 17-beta-diol | hmdb | | 5-alpha-androstane-3-alpha-17-beta-diol | hmdb | | Androstane-3,17-diol | hmdb |
|
|---|
| Chemical Formula | C19H32O2 |
|---|
| IUPAC name | (1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol |
|---|
| InChI Identifier | InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1 |
|---|
| InChI Key | CBMYJHIOYJEBSB-UNPXRYTGSA-N |
|---|
| Isomeric SMILES | [H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C |
|---|
| Average Molecular Weight | 292.4562 |
|---|
| Monoisotopic Molecular Weight | 292.240230268 |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Steroids and steroid derivatives |
|---|
| Sub Class | Androstane steroids |
|---|
| Direct Parent | Androgens and derivatives |
|---|
| Alternative Parents | |
|---|
| Substituents | - Androgen-skeleton
- 17-hydroxysteroid
- 3-alpha-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
|
|---|
| Molecular Framework | Aliphatic homopolycyclic compounds |
|---|
| External Descriptors | - C19 steroids (androgens) and derivatives (C07632 )
- Androstane and derivatives (C07632 )
|
|---|
| Physico-Chemical Properties - Experimental |
|---|
| Property | Value | Reference |
|---|
| Experimental logP | Not Available | |
|---|
| Experimental Water Solubility | Not Available | |
|---|
| Melting Point | Not Available | |
|---|
|
| Foods of Origin |
|---|
| Food | Content Range | Average | Reference |
|---|
| Food | | | Reference |
|---|
|
| Production Data |
|---|
| Production Method | commercial |
|---|
| Production Method Reference | Not Available |
|---|
| Production Method Reference File | Not Available |
|---|
| Quantity Available | Production upon request |
|---|
| Delivery Time | Not Available |
|---|
| Storage Form | solid |
|---|
| Storage Conditions | -80°C |
|---|
| Stability | Not Available |
|---|
| Purity | Not Available |
|---|
| Spectra |
|---|
| Spectral Data Upon Request | Not Available |
|---|
| Provider Information |
|---|
|
| Commercial Vendors |
|---|
| Not Available |
