Showing Compound Card for Farnesylcysteine (CDB004993)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-17 18:58:15 UTC
Updated at2020-12-07 19:11:25 UTC
CannabisDB IDCDB004993
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFarnesylcysteine
DescriptionFarnesylcysteine belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Farnesylcysteine is a very strong basic compound (based on its pKa). Farnesylcysteine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight325.51
Monoisotopic Molecular Weight325.2075
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
CC(C)=CCC\C(C)=C\CC\C(C)=C\CSC[C@H](N)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
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFarnesylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00mx-9751000000-c75df345d8656012bdf0Spectrum
Predicted GC-MSFarnesylcysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05aa-8954000000-cb16d7122a6e7b9bef6cSpectrum
Predicted GC-MSFarnesylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-5396000000-851334288f8263d03d232017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9860000000-dba878d9fc5362b671952017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adl-9510000000-bd3c119811a4e2799abe2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-1659000000-855d9d7f127560943e3d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-4791000000-842def471e9561591a942017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fer-9210000000-618508fb705b5020cbb62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aba-1951000000-c167818276c3885878f52021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-2910000000-002b04adc9b951f37f542021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c29-9410000000-00bddc91238723c07f722021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-1193000000-d24d7910416af3a098632021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-9060000000-023ebf01c668a96e16732021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9110000000-d96ba181641b84daf9052021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Prenylcysteine oxidase 1PCYOX12p13.3Q9UHG3 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0011627
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
General ReferencesNot Available

Enzymes

Enzyme Details
1. Prenylcysteine oxidase 1
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