Farnesylcysteine (CHEM040376)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:35:09 UTC
Update Date2016-11-09 01:22:14 UTC
Accession NumberCHEM040376
Identification
Common NameFarnesylcysteine
ClassSmall Molecule
DescriptionAn amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of S-[(2E,6E)]-farnesyl-L-cysteine; major species at pH 7.3.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
S-(2E,6E)-Farnesyl-L-cysteineChEBI
S-trans-trans-FarnesylcysteineKegg
(e,e)-L-S-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-cysteineHMDB
S-all-trans-Farnesyl-L-cysteineHMDB
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, HMDB
S-FarnesylcysteineMeSH, HMDB
Chemical FormulaC18H31NO2S
Average Molecular Mass325.509 g/mol
Monoisotopic Mass325.208 g/mol
CAS Registry Number68000-92-0
IUPAC Name(2R)-2-amino-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid
Traditional NameS-farnesylcysteine
SMILESN[C@@H](CSC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O
InChI IdentifierInChI=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
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mx-9751000000-c75df345d8656012bdf0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05aa-8954000000-cb16d7122a6e7b9bef6cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-5396000000-851334288f8263d03d23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9860000000-dba878d9fc5362b67195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adl-9510000000-bd3c119811a4e2799abeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-1659000000-855d9d7f127560943e3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-4791000000-842def471e9561591a94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fer-9210000000-618508fb705b5020cbb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aba-1951000000-c167818276c3885878f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-2910000000-002b04adc9b951f37f54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c29-9410000000-00bddc91238723c07f72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-1193000000-d24d7910416af3a09863Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-9060000000-023ebf01c668a96e1673Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9110000000-d96ba181641b84daf905Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011627
FooDB IDFDB028328
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-12581
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4942854
ChEBI ID62141
PubChem Compound ID6438372
Kegg Compound IDC19691
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17425716
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
9. 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.
10. 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.
11. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
12. The lipid handbook with CD-ROM