Geranylgeranylcysteine (CHEM040408)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 20:36:15 UTC
Update Date2016-11-09 01:22:15 UTC
Accession NumberCHEM040408
Identification
Common NameGeranylgeranylcysteine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
S-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl)-(e,e,e)-L-cysteineHMDB
S-[(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl]- (9ci)-L-cysteineHMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulfanylpropanoateGenerator, HMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulphanylpropanoateGenerator, HMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulphanylpropanoic acidGenerator, HMDB
Chemical FormulaC23H37NO3S
Average Molecular Mass407.610 g/mol
Monoisotopic Mass407.249 g/mol
CAS Registry Number169523-06-2
IUPAC Name(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid
Traditional Name(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid
SMILESSC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O
InChI IdentifierInChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1
InChI KeyUBCKUGRWFMEXIF-WONWMLGISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • N-acyl-amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Alkylthiol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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 Solubility0.0017 g/LALOGPS
logP5.58ALOGPS
logP5.65ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)1.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity123.68 m³·mol⁻¹ChemAxon
Polarizability48.79 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-8889000000-3f81e03325547663218eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-022l-9352500000-a735063f6d3013ad3130Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2769600000-ec3a2eaceb3ae67eb426Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ads-4961000000-44253e7d991961cef89dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-8950000000-13cfd8c2ae6c7a125a61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-2017900000-84ecb7d4aa334cb77ecfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-4329200000-97099be07e7e001431c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008l-9350000000-4a227b58aca7450e328bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0192200000-5cc299ff4ab00e2154d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ei-2890000000-3dbfcbdc69c287f49fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m0-7900000000-ebaf835d361f6930eb39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-6bfbdf0cbf1824b2f5c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-071l-9855100000-cb7896acb5225696b6a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-9262000000-74db85fe9f128c11af64Spectrum
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 IDHMDB0011678
FooDB IDFDB028366
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776596
ChEBI IDNot Available
PubChem Compound ID53481025
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zhang L, Tschantz WR, Casey PJ: Isolation and characterization of a prenylcysteine lyase from bovine brain. J Biol Chem. 1997 Sep 12;272(37):23354-9.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. 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.
4. 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.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM