| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:25:43 UTC |
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| Update Date | 2020-04-22 15:18:30 UTC |
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| BMDB ID | BMDB0006763 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 20a,22b-Dihydroxycholesterol |
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| Description | 20a,22b-Dihydroxycholesterol belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. 20a,22b-Dihydroxycholesterol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 20a,22b-Dihydroxycholesterol participates in a number of enzymatic reactions, within cattle. In particular, 20a,22b-Dihydroxycholesterol can be converted into pregnenolone and 4-methylpentanal through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 20a,22b-Dihydroxycholesterol can be biosynthesized from 22b-hydroxycholesterol through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In cattle, 20a,22b-dihydroxycholesterol is involved in the metabolic pathway called the steroidogenesis pathway. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 20alpha,22beta-Dihydroxycholesterol | HMDB |
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| Chemical Formula | C27H46O3 |
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| Average Molecular Weight | 418.6523 |
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| Monoisotopic Molecular Weight | 418.344695338 |
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| IUPAC Name | (2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol |
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| Traditional Name | (2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol |
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| CAS Registry Number | 15234-55-6 |
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| SMILES | [H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C |
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| InChI Identifier | InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19?,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1 |
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| InChI Key | ISBSSBGEYIBVTO-IVMOZYHGSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. |
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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 | Bile acids, alcohols and derivatives |
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| Direct Parent | Trihydroxy bile acids, alcohols and derivatives |
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| Alternative Parents | |
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| Substituents | - Cholesterol
- Cholesterol-skeleton
- Cholestane-skeleton
- Trihydroxy bile acid, alcohol, or derivatives
- 22-hydroxysteroid
- 20-hydroxysteroid
- Hydroxysteroid
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Delta-5-steroid
- Cyclic alcohol
- Tertiary alcohol
- Secondary alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- 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 | Expected 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 | |
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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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