Record Information |
---|
Version | 5.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2007-05-22 19:16:51 UTC |
---|
Update Date | 2022-03-07 02:49:30 UTC |
---|
HMDB ID | HMDB0006247 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | 25-Hydroxycholesterol |
---|
Description | 25-Hydroxycholesterol is steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). It also induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases. 25-Hydroxycholesterol also enhances Interleukin-1 beta (IL-1beta-induced) IL-8 production.(PMID: 17086498 ). 25-hydroxycholesterol is endogenously produced from cholesterol at early time intervals after cholesterol ingestion. It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge. |
---|
Structure | [H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23?,24?,26+,27-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(beta)-Cholest-5-ene-3-25-diol | HMDB | 25-Hydroxy-cholesterol | HMDB | 25-Hydroxycholest-5-en-3-ol | HMDB | 5-Cholestene-3beta-25-diol | HMDB | Cholest-5-en-3beta-25-diol | HMDB | Cholest-5-ene-3-b,25-diol | HMDB | Cholest-5-ene-3-beta,25-diol | HMDB | Cholest-5-ene-3beta-25-diol | HMDB |
|
---|
Chemical Formula | C27H46O2 |
---|
Average Molecular Weight | 402.6529 |
---|
Monoisotopic Molecular Weight | 402.349780716 |
---|
IUPAC Name | (2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol |
---|
Traditional Name | (2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol |
---|
CAS Registry Number | 2140-46-7 |
---|
SMILES | [H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C |
---|
InChI Identifier | InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23?,24?,26+,27-/m1/s1 |
---|
InChI Key | INBGSXNNRGWLJU-POAVOMIWSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Cholestane steroids |
---|
Direct Parent | Cholesterols and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Cholesterol
- Cholesterol-skeleton
- 25-hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- Hydroxysteroid
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- 3-beta-hydroxysteroid
- Delta-5-steroid
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
|
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | |
---|
Disposition | |
---|
Process | |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | 172 - 173 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Experimental Collision Cross Sections |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
25-Hydroxycholesterol,1TMS,isomer #1 | C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C | 3381.3 | Semi standard non polar | 33892256 | 25-Hydroxycholesterol,1TMS,isomer #2 | C[C@H](CCCC(C)(C)O)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C | 3342.1 | Semi standard non polar | 33892256 | 25-Hydroxycholesterol,2TMS,isomer #1 | C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C | 3403.9 | Semi standard non polar | 33892256 | 25-Hydroxycholesterol,1TBDMS,isomer #1 | C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C | 3616.9 | Semi standard non polar | 33892256 | 25-Hydroxycholesterol,1TBDMS,isomer #2 | C[C@H](CCCC(C)(C)O)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C | 3559.9 | Semi standard non polar | 33892256 | 25-Hydroxycholesterol,2TBDMS,isomer #1 | C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C | 3841.6 | Semi standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - 25-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive | splash10-059l-1009000000-cec357bcbaf7149e29f5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 25-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positive | splash10-001i-2211390000-0527cfa38749e09bd2b6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 25-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Positive-QTOF | splash10-00kr-0009100000-9e729aebf6add28b22e8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Positive-QTOF | splash10-0170-1109000000-3349124bb19a8fd2ee08 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Positive-QTOF | splash10-02di-2239000000-7a23aff71704f1c442ac | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Negative-QTOF | splash10-0udi-0003900000-bc39f53a2f47d9e530b4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Negative-QTOF | splash10-0ue9-0009600000-14eb751b01166860ee82 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Negative-QTOF | splash10-00kr-1019000000-981e4ae54c86fe2b7d18 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Negative-QTOF | splash10-0udi-0000900000-079f76b4d985e4b92c9d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Negative-QTOF | splash10-0udi-0001900000-25ec6288bc3521fc5e32 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Negative-QTOF | splash10-0udj-0039300000-b49af36b609e46ef3701 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Positive-QTOF | splash10-00kr-0309000000-94663290c06fb4528adf | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Positive-QTOF | splash10-014i-8669100000-8343de835a906d68edec | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Positive-QTOF | splash10-0a4i-5952000000-e7e8f0bed73a8187daa3 | 2021-09-25 | Wishart Lab | View Spectrum |
|
---|