| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2007-05-22 14:50:56 -0600 |
| Update Date |
2013-02-08 17:14:42 -0700 |
| HMDB ID |
HMDB06271 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Zymosterol intermediate 2 |
| Description |
Zymosterol is the precursor of cholesterol and is found in the plasma membrane. zymosterol circulates within the cells. The structural features of zymosterol provided optimal substrate acceptability. In human fibroblasts, zymosterol is converted to cholesterol solely in the rough ER. Little or no zymosterol or cholesterol accumulates in the rough ER in vivo. Newly synthesized zymosterol moves to the plasma membrane without a detectable lag and with a half-time of 9 min, about twice as fast as cholesterol. The pool of radiolabeled zymosterol in the plasma membrane turns over rapidly, faster than does intracellular cholesterol. Thus, plasma membrane zymosterol is not stagnant. [3H]Zymosterol pulsed into intact cells is initially found in the plasma membrane. (PMID: 1939176  ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (3b,5a)- Cholesta-8,24-dien-3-ol
- 5alpha-Cholesta-8,24-dien-3beta-ol
- Cholest-8,24-dien-3b-ol
- Cholesta-8,24-dien-3-ol
- Delta8,24-Cholestadien-3beta-ol
- Zymosterol
|
| Chemical Formula |
C27H44O |
| Average Molecular Weight |
384.6377 |
| Monoisotopic Molecular Weight |
384.33921603 |
| IUPAC Name |
(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol |
| Traditional IUPAC Name |
zymosterol |
| CAS Registry Number |
128-33-6 |
| SMILES |
[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3 |
| InChI Identifier |
InChI=1S/C27H44O/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/h7,19-21,23-24,28H,6,8-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1 |
| InChI Key |
CGSJXLIKVBJVRY-XTGBIJOFSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Steroids and Steroid Derivatives |
| Sub Class |
Cholesterols and Derivatives |
| Other Descriptors |
- 3beta-sterol(ChEBI)
- Aliphatic Homopolycyclic Compounds
- Cholesterol and derivatives(KEGG)
- Cholesterol and derivatives(Lipidmaps)
|
| Substituents |
- 3 Hydroxy Steroid
- Cyclic Alcohol
- Cyclohexane
- Cyclohexene
- Isoprene
- Secondary Alcohol
- Sesterterpene
|
| Direct Parent |
Cholesterols and Derivatives |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Hormones, Membrane component
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
- Extracellular
- Membrane
- Endoplasmic reticulum
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
110 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
- Extracellular
- Membrane
- Endoplasmic reticulum
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
|
| Pathways |
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023869 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
83724 |
| KEGG Compound ID |
C05437 |
| BioCyc ID |
Not Available |
| BiGG ID |
1454806 |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB06271 |
| Metagene Link |
HMDB06271 |
| METLIN ID |
Not Available |
| PubChem Compound |
92746 |
| PDB ID |
Not Available |
| ChEBI ID |
18252 |
| References |
|---|
| Synthesis Reference |
Dolle, Roland E.; Schmidt, Stanley J.; Kruse, Lawrence I. Synthesis of zymosterol: salient intermediate of fungal and mammalian sterol biosynthesis. Journal of the Chemical Society, Chemical Communications (1988), (1), 19-21. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
