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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-01-30 09:59:52 UTC
Update Date2019-07-23 05:56:11 UTC
HMDB IDHMDB0011627
Secondary Accession Numbers
  • HMDB11627
Metabolite Identification
Common NameFarnesylcysteine
DescriptionIn patients with chronic fatigue syndrome (CFS) we found increased IgM levels to S-farnesyl-L-cysteine. S-farnesyl-L-cysteine plays a key role in regulating cell growth, differentiation and apoptosis through RAS protein activity. The latter depends on their anchorage to the inner surface of the plasma membrane, which is promoted by their common carboxy-terminal S-farnesyl-cysteine. The presence of antibodies to S-farnesyl-L-cysteine suggest that RAS functions may have undergone damage by oxidative/nitrosative stress, causing disturbed functional activity in the regulation of cell growth. (PMID 17159817 ).
Structure
Data?1563861371
Synonyms
ValueSource
S-(2E,6E)-Farnesyl-L-cysteineChEBI
(e,e)-L-S-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-cysteineHMDB
S-all-trans-Farnesyl-L-cysteineHMDB
S-trans-trans-FarnesylcysteineHMDB
S-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl]-L-cysteineHMDB
S-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienyl]-L-cysteine,(9ci)HMDB
S-Farnesyl cysteineMeSH
Chemical FormulaC18H31NO2S
Average Molecular Weight325.509
Monoisotopic Molecular Weight325.207549931
IUPAC Name(2R)-2-amino-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid
Traditional NameS-farnesylcysteine
CAS Registry Number68000-92-0
SMILES
N[C@@H](CSC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O
InChI Identifier
InChI=1S/C18H31NO2S/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-22-13-17(19)18(20)21/h7,9,11,17H,5-6,8,10,12-13,19H2,1-4H3,(H,20,21)/b15-9+,16-11+/t17-/m0/s1
InChI KeySYSLNQMKLROGCL-BCYUYYMPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Farsesane sesquiterpenoid
  • L-cysteine-s-conjugate
  • Cysteine or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Amino acid or derivatives
  • Amino acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0051 g/LALOGPS
logP1.48ALOGPS
logP2.17ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity99.65 m³·mol⁻¹ChemAxon
Polarizability39.43 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mx-9751000000-c75df345d8656012bdf0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05aa-8954000000-cb16d7122a6e7b9bef6cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-5396000000-851334288f8263d03d23JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9860000000-dba878d9fc5362b67195JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adl-9510000000-bd3c119811a4e2799abeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-1659000000-855d9d7f127560943e3dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-4791000000-842def471e9561591a94JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fer-9210000000-618508fb705b5020cbb6JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028328
KNApSAcK IDNot Available
Chemspider ID4942854
KEGG Compound IDC19691
BioCyc IDCPD-12581
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438372
PDB IDNot Available
ChEBI ID62141
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Maes M, Mihaylova I, Leunis JC: Chronic fatigue syndrome is accompanied by an IgM-related immune response directed against neopitopes formed by oxidative or nitrosative damage to lipids and proteins. Neuro Endocrinol Lett. 2006 Oct;27(5):615-21. [PubMed:17159817 ]
  2. Lamango NS, Charlton CG: Farnesyl-L-cysteine analogs block SAM-induced Parkinson's disease-like symptoms in rats. Pharmacol Biochem Behav. 2000 Aug;66(4):841-9. [PubMed:10973524 ]
  3. Havel CM, Fisher P, Watson JA: Isopentenoid synthesis in embryonic Drosophila cells: prenylated protein profile and prenyl group usage. Arch Biochem Biophys. 1992 Jun;295(2):410-20. [PubMed:1586169 ]
  4. Aharonson Z, Gana-Weisz M, Varsano T, Haklai R, Marciano D, Kloog Y: Stringent structural requirements for anti-Ras activity of S-prenyl analogues. Biochim Biophys Acta. 1998 Feb 27;1406(1):40-50. [PubMed:9545527 ]
  5. Elad G, Paz A, Haklai R, Marciano D, Cox A, Kloog Y: Targeting of K-Ras 4B by S-trans,trans-farnesyl thiosalicylic acid. Biochim Biophys Acta. 1999 Dec 9;1452(3):228-42. [PubMed:10590312 ]
  6. Volker C, Miller RA, McCleary WR, Rao A, Poenie M, Backer JM, Stock JB: Effects of farnesylcysteine analogs on protein carboxyl methylation and signal transduction. J Biol Chem. 1991 Nov 15;266(32):21515-22. [PubMed:1939182 ]
  7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  8. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  9. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  10. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Involved in the degradation of prenylated proteins. Cleaves the thioether bond of prenyl-L-cysteines, such as farnesylcysteine and geranylgeranylcysteine.
Gene Name:
PCYOX1
Uniprot ID:
Q9UHG3
Molecular weight:
56639.66
Reactions
Farnesylcysteine + Oxygen + Water → 2-trans,6-trans-Farnesal + L-Cysteine + Hydrogen peroxidedetails