Showing Compound S-(2E,6E)-farnesyl-L-cysteine (FDB031148)

Record Information

Version

1.0

Creation date

2015-05-07 21:09:32 UTC

Update date

2019-11-26 03:22:10 UTC

Primary ID

FDB031148

Secondary Accession Numbers

FDB028328

Chemical Information

FooDB Name

S-(2E,6E)-farnesyl-L-cysteine

Description

Farnesylcysteine, also known as S-trans-trans-farnesylcysteine or S-(2e,6e)-farnesyl-L-cysteine, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Farnesylcysteine is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Farnesylcysteine can be found in a number of food items such as pulses, mentha (mint), horned melon, and lentils, which makes farnesylcysteine a potential biomarker for the consumption of these food products.

CAS Number

68000-92-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
(e,e)-L-S-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-cysteine	HMDB
S-(2E,6E)-Farnesyl-L-cysteine	ChEBI
S-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl]-L-cysteine	HMDB
S-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienyl]-L-cysteine,(9ci)	HMDB
S-all-trans-Farnesyl-L-cysteine	HMDB
S-Farnesyl cysteine	MeSH, HMDB
S-Farnesylcysteine	MeSH, HMDB
S-trans-trans-Farnesylcysteine	Kegg

Showing 1 to 8 of 8 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0051 g/L	ALOGPS
logP	1.48	ALOGPS
logP	2.17	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.56	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	99.65 m³·mol⁻¹	ChemAxon
Polarizability	39.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H31NO2S

IUPAC name

(2R)-2-amino-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid

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

Isomeric SMILES

N[C@@H](CSC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O

Average Molecular Weight

325.509

Monoisotopic Molecular Weight

325.207549931

Classification

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

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 Framework

Aliphatic acyclic compounds

External Descriptors

S-farnesyl-L-cysteine (CHEBI:62197 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Plant:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Farnesylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00mx-9751000000-c75df345d8656012bdf0	Spectrum
Predicted GC-MS	Farnesylcysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05aa-8954000000-cb16d7122a6e7b9bef6c	Spectrum
Predicted GC-MS	Farnesylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a7i-5396000000-851334288f8263d03d23	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-9860000000-dba878d9fc5362b67195	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0adl-9510000000-bd3c119811a4e2799abe	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dr-1659000000-855d9d7f127560943e3d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-4791000000-842def471e9561591a94	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fer-9210000000-618508fb705b5020cbb6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aba-1951000000-c167818276c3885878f5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-2910000000-002b04adc9b951f37f54	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c29-9410000000-00bddc91238723c07f72	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-1193000000-d24d7910416af3a09863	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-9060000000-023ebf01c668a96e1673	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9110000000-d96ba181641b84daf905	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Abalone	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Abiyuch	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Acerola	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Acorn	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Adzuki bean	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Agar	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Agave	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alaska blueberry	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alaska wild rhubarb	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Alfalfa	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis