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Human Metabolome Database Version 3.5

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Showing metabocard for Farnesylcysteine (HMDB11627)

Record Information
Version 3.5
Creation Date 2009-01-30 02:59:52 -0700
Update Date 2013-05-29 13:46:30 -0600
HMDB ID HMDB11627
Secondary Accession Numbers None
Metabolite Identification
Common Name Farnesylcysteine
Description In 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (E,E)-L-S-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-Cysteine
  2. Farnesylcysteine
  3. S-All-trans-Farnesyl-L-cysteine
  4. S-trans-trans-Farnesylcysteine
  5. S-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl]-L-Cysteine
  6. S-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienyl]-L-Cysteine,(9CI)
Chemical Formula C18H31NO2S
Average Molecular Weight 325.509
Monoisotopic Molecular Weight 325.207549931
IUPAC Name (2R)-2-amino-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid
Traditional IUPAC Name (2R)-2-amino-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid
CAS Registry Number 68000-92-0
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 Key SYSLNQMKLROGCL-BCYUYYMPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Sesquiterpenes
Substituents
  • Acyclic Alkene
  • Carboxylic Acid
  • Isoprene
  • Primary Aliphatic Amine (Alkylamine)
  • Thioether
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0051 g/L ALOGPS
LogP 1.48 ALOGPS
LogP 2.17 ChemAxon
LogS -4.81 ALOGPS
pKa (strongest acidic) 2.56 ChemAxon
pKa (strongest basic) 9.14 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 63.32 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 99.65 ChemAxon
Polarizability 39.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028328
KNApSAcK ID Not Available
Chemspider ID 4942854 Link_out
KEGG Compound ID C19691 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11627 Link_out
Metagene Link HMDB11627 Link_out
METLIN ID Not Available
PubChem Compound 6438372 Link_out
PDB ID Not Available
ChEBI ID 62141 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Prenylcysteine oxidase 1
Reactions:
Farnesylcysteine + Oxygen + Water unknown 2-trans,6-trans-Farnesal + L-Cysteine + Hydrogen peroxide details
Gene Name: PCYOX1
Uniprot ID: Q9UHG3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA