Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 09:27:14 UTC |
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Update Date | 2020-02-26 21:24:55 UTC |
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HMDB ID | HMDB0004035 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 22b-Hydroxycholesterol |
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Description | 22b-Hydroxycholesterol, also known as cholest-5-en-3b,22R-diol or 22(R)OH cholesterol, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Thus, 22b-hydroxycholesterol is considered to be a sterol lipid molecule. 22b-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. |
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Structure | |
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Synonyms | Value | Source |
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(3beta,22R)-Cholest-5-ene-3,22-diol | ChEBI | 22beta-Hydroxycholesterol | ChEBI | 22R-Hydroxycholesterol | ChEBI | Cholest-5-en-3beta,22R-diol | ChEBI | (22R)-22-Hydroxycholesterol | Kegg | (3b,22R)-Cholest-5-ene-3,22-diol | Generator | (3Β,22R)-cholest-5-ene-3,22-diol | Generator | 22Β-hydroxycholesterol | Generator | Cholest-5-en-3b,22R-diol | Generator | Cholest-5-en-3β,22R-diol | Generator | 22-Hydroxycholesterol, (3beta,20R,22R)-isomer | HMDB | 22-Hydroxycholesterol, (3beta,20R,22S)-isomer | HMDB | Cholest-5-ene-3beta,22-diol | HMDB | 22(R)-Hydroxycholesterol | HMDB | 22-Hydroxycholesterol, (3beta,22S)-isomer | HMDB | 22(R)OH Cholesterol | HMDB | 22-Hydroxycholesterol | HMDB | 22-Hydroxycholesterol, (3beta,22R)-isomer | HMDB | 22S-Hydroxycholesterol | HMDB |
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Chemical Formula | C27H46O2 |
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Average Molecular Weight | 402.6529 |
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Monoisotopic Molecular Weight | 402.349780716 |
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IUPAC Name | (1S,2R,5S,10S,11S,14R,15S)-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol |
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Traditional Name | 22R-hydroxycholesterol |
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CAS Registry Number | 22348-64-7 |
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SMILES | [H][C@@]12CC[C@H]([C@H](C)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C |
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InChI Identifier | InChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25+,26-,27+/m0/s1 |
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InChI Key | RZPAXNJLEKLXNO-GFKLAVDKSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid 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 | Dihydroxy bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - Cholesterol
- Cholesterol-skeleton
- Cholestane-skeleton
- Dihydroxy bile acid, alcohol, or derivatives
- 22-hydroxysteroid
- Hydroxysteroid
- 3-hydroxy-delta-5-steroid
- 3-beta-hydroxysteroid
- 3-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic 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 | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dr-1009000000-ed60780a407ecfba86a3 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-001i-2111490000-e04dc3bb7ab36f5571f8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f79-0009200000-2ae8fb6172d46e818cef | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-2119100000-9925177c38f63ddc14a1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-6049000000-44d8c7fcd6055391f8dd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0004900000-10b9f0186b2a2ac37d53 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ue9-1019700000-6b5a6ee8410d635f82c6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f79-4059000000-8d88574ef4b0b7d39b85 | Spectrum |
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General References | - Haidar B, Denis M, Marcil M, Krimbou L, Genest J Jr: Apolipoprotein A-I activates cellular cAMP signaling through the ABCA1 transporter. J Biol Chem. 2004 Mar 12;279(11):9963-9. Epub 2003 Dec 29. [PubMed:14701824 ]
- Yao ZX, Brown RC, Teper G, Greeson J, Papadopoulos V: 22R-Hydroxycholesterol protects neuronal cells from beta-amyloid-induced cytotoxicity by binding to beta-amyloid peptide. J Neurochem. 2002 Dec;83(5):1110-9. [PubMed:12437582 ]
- Matsuzaki J, Tsuji T, Imazeki I, Ikeda H, Nishimura T: Immunosteroid as a regulator for Th1/Th2 balance: its possible role in autoimmune diseases. Autoimmunity. 2005 Aug;38(5):369-75. [PubMed:16227152 ]
- Tuckey RC: Cholesterol side-chain cleavage by mitochondria from the human placenta. Studies using hydroxycholesterols as substrates. J Steroid Biochem Mol Biol. 1992 Sep;42(8):883-90. [PubMed:1525048 ]
- Hanley K, Ng DC, He SS, Lau P, Min K, Elias PM, Bikle DD, Mangelsdorf DJ, Williams ML, Feingold KR: Oxysterols induce differentiation in human keratinocytes and increase Ap-1-dependent involucrin transcription. J Invest Dermatol. 2000 Mar;114(3):545-53. [PubMed:10692116 ]
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