| Identification |
|---|
| YMDB ID | YMDB00313 |
|---|
| Name | Cholesterol |
|---|
| Species | Saccharomyces cerevisiae |
|---|
| Strain | Baker's yeast |
|---|
| Description | Cholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cholesterol is a potentially toxic compound. |
|---|
| Structure | |
|---|
| Synonyms | - (-)-Cholesterol
- (+)-ent-Cholesterol
- (20bFH)-cholest-5-en-3b-ol
- (3b)-cholest-5-en-3-ol
- (3beta)-Cholest-5-en-3-ol
- 20-epi-cholesterol
- 20-iso-cholesterol
- 20bFH-cholest-5-en-3b-ol
- 3beta-Hydroxycholest-5-ene
- 5-Cholesten-3B-ol
- 5-Cholesten-3beta-ol
- 5:6-Cholesten-3-ol
- 5:6-Cholesten-3beta-ol
- Cholest-5-en-3-ol
- cholest-5-en-3b-ol
- Cholest-5-en-3beta-ol
- Cholesterin
- Cholesterine
- Cholesterol
- Cholesterol base H
- Cholesteryl alcohol
- Cholestrin
- Cholestrol
- Cordulan
- Dastar
- Dusoline
- Dusoran
- Dythol
- epicholesterin
- Epicholesterol
- Hydrocerin
- Kathro
- Lanol
- Nimco cholesterol base H
- Super hartolan
- Tegolan
- Fancol CH
- Liquid crystal CN/9
- nimco Cholesterol base no. 712
|
|---|
| CAS number | 57-88-5 |
|---|
| Weight | Average: 386.6535
Monoisotopic: 386.354866094 |
|---|
| InChI Key | HVYWMOMLDIMFJA-FNOPAARDSA-N |
|---|
| InChI | InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21?,22+,23-,24+,25+,26+,27-/m1/s1 |
|---|
| IUPAC Name | (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol |
|---|
| Traditional IUPAC Name | cholest-5-en-3-ol |
|---|
| Chemical Formula | C27H46O |
|---|
| SMILES | [H]OC1([H])C([H])([H])C2=C([H])C([H])([H])[C@@]3([H])[C@]4([H])C([H])([H])C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3([H])[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H] |
|---|
| 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-skeleton
- Cholesterol
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-5-steroid
- Delta-5-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
|
|---|
| Molecular Framework | Aliphatic homopolycyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Charge | 0 |
|---|
| Melting point | 148 °C |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Water Solubility | 9.5e-05 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | | LogP | Not Available | PhysProp |
|
|---|
| Predicted Properties | |
|---|
| Biological Properties |
|---|
| Cellular Locations | Not Available |
|---|
| Organoleptic Properties | Not Available |
|---|
| SMPDB Pathways | | Cholesterol biosynthesis and metabolism CE(10:0) | PW002545 |    | | Cholesterol biosynthesis and metabolism CE(12:0) | PW002548 |    | | Cholesterol biosynthesis and metabolism CE(14:0) | PW002544 |    | | Cholesterol biosynthesis and metabolism CE(16:0) | PW002550 |    | | Cholesterol biosynthesis and metabolism CE(18:0) | PW002551 |    |
|
|---|
| KEGG Pathways | |
|---|
| SMPDB Reactions | |
|---|
| KEGG Reactions | Not Available |
|---|
| Concentrations |
|---|
| Intracellular Concentrations | Not Available |
|---|
| Extracellular Concentrations | Not Available |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | View |
|---|
| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05fr-1109000000-3cc42021add80e72c319 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0006-3104900000-698223f49da0b0c1cf81 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014r-0009000000-dccd68f70545aeac4fab | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05p9-3149000000-7f25daf2b709c7e0d177 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0c00-6269000000-5333d0216e01a3e43367 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0009000000-dc853b29b9e884bbb03b | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0009000000-09d9608700564a6fef78 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ldi-1009000000-96f6e67651380e1c959e | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
|
|---|
| References |
|---|
| References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
|
|---|
| Synthesis Reference: | Zhu, Yongming; Qin, Liena; Liu, Rui. Simple method for synthesis cholesterol from Diosgenin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9 pp. |
|---|
| External Links: | |
|---|
