CAS 68000-92-0 Farnesylcysteine (HCID 6438372)

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Basic information

CAS: 68000-92-0
Standard SMILES: CC(C)=CCC/C(C)=C/CC/C(C)=C/CSC[C@H](N)C(=O)O
InChIKey: SYSLNQMKLROGCL-BCYUYYMPSA-N
Molecular formula: C18H31NO2S
Average molar mass: 325.5 g/mol
Monoisotopic mass: 325.20755023

Overview

S-[(2E,6E)-farnesyl]-L-cysteine is an S-farnesyl-L-cysteine where the C=C double bonds at the 2- and 6-positions both have (E)-configuration. It is a tautomer of a S-[(2E,6E)-farnesyl]-L-cysteine zwitterion.

Names & identifiers

Preferred name: Farnesylcysteine
IUPAC: (2R)-2-amino-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylpropanoic acid
English name: Farnesyl cysteine
Molecular formula: C18H31NO2S
Molecular weight: 325.51

Names & synonyms

S-farnesylcysteineFarnesylcysteine68000-92-059S52SU9NV(2R)-2-amino-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylpropanoic acidDTXSID501316758(2R)-2-amino-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acidL-Cysteine, S-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-, (E,E)-(2R)-2-amino-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)sulfanylpropanoic acid(2R)-2-amino-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)sulfanyl)propanoic acidRefChem:921472DTXCID001746588

Show more names

Farnesyl-L-cysteineL-Cysteine, S-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]-

(2R)-2-azaniumyl-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)sulfanylpropanoateS-Farnesyl cysteinetrans-farnesyl-L-cysteineS-[(2E,6E)-farnesyl]-L-cysteineS-trans-trans-FarnesylcysteineS-all-trans-Farnesyl-L-cysteineCHEBI:62197farnesyl cysteine

Properties

Computed structural properties

XLogP: 2.5
Topological polar surface area: 88.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 11
Heavy atoms: 22
Formal charge: 0
Complexity: 421

Experimental & physicochemical properties

Physical DescriptionSolid

Physicochemical properties

Melting point: 148 · 148-150 °C
Boiling point: 473.3 · 473.3±45.0 °C(Predicted)
Density: 1.021 · 1.021±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
pka: 2.08 · 2.08±0.10(Predicted)
form: powder
FDA UNII: 59 S52SU9NV · 59S52SU9NV
UNSPSC Code: 12352211 · 12352211
NACRES: 25 · NA.25
WGK Germany: 3 · WGK 3
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

wgk: WGK 3
Storage Class: 11 - Combustible Solids

Chemistry & industry

Pharmacology

Cellular LocationsMembrane

Applications · 1 item

UsesFarnesylcysteine (FC) is a competitive inhibitor of ICMT. The fcly mutant has quantitatively low farnesylcysteine (FC) lyase activity and an enhanced response to ABA. Farnesylcysteine induces an ABA hypersensitive phenotype in Arabidopsis thaliana[1].