AFCDB: L-Cysteine (FDB012678)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:18 UTC

Update date

2020-09-17 15:38:37 UTC

Primary ID

FDB012678

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Cysteine

Description

L-Cysteine, also known as C or e 920, belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Cysteine is a drug which is used for the prevention of liver damage and kidney damage associated with overdoses of acetaminophen. L-Cysteine is a very strong basic compound (based on its pKa). L-Cysteine exists in all living species, ranging from bacteria to humans. Within humans, L-cysteine participates in a number of enzymatic reactions. In particular, L-cysteine can be converted into 3-sulfinoalanine; which is mediated by the enzyme cysteine dioxygenase type 1. In addition, L-cysteine can be converted into hydrogen sulfide and pyruvic acid through the action of the enzyme cystathionine gamma-lyase. In humans, L-cysteine is involved in cysteine metabolism. L-Cysteine is a sulfury tasting compound. Outside of the human body, L-Cysteine is found, on average, in the highest concentration within a few different foods, such as sunflowers, soy beans, and watermelons and in a lower concentration in common wheats, dates, and beers. L-Cysteine has also been detected, but not quantified in, several different foods, such as oyster mushrooms, salmonberries, rapes, safflowers, and cupuaçus. This could make L-cysteine a potential biomarker for the consumption of these foods. L-Cysteine is a potentially toxic compound. An optically active form of cysteine having L-configuration.

CAS Number

52-90-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	23.1 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.8	ChemAxon
logS	-0.72	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	9.05	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	28.22 m³·mol⁻¹	ChemAxon
Polarizability	11.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C3H7NO2S

IUPAC name

(2R)-2-amino-3-sulfanylpropanoic acid

InChI Identifier

InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

InChI Key

XUJNEKJLAYXESH-REOHCLBHSA-N

Isomeric SMILES

N[C@@H](CS)C(O)=O

Average Molecular Weight

121.158

Monoisotopic Molecular Weight

121.019749163

Classification

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
L-alpha-amino acid
Amino acid
Alkylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:17561 )
L-alpha-amino acid (CHEBI:17561 )
cysteine (CHEBI:17561 )
serine family amino acid (CHEBI:17561 )
Common amino acids (C00097 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 29.74%; H 5.82%; N 11.56%; O 26.41%; S 26.47%	DFC
Melting Point	Mp 178° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	277 mg/mL at 25 oC	BEILSTEIN
Experimental logP	-2.49	HANSCH,C ET AL. (1995)
Experimental pKa	pKa3 10.46 (SH)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +26.5 (5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Cysteine, 4 TMS, GC-MS Spectrum	splash10-00kb-0950000000-df7e91c95b610ff21c79	Spectrum
GC-MS	L-Cysteine, 4 TMS, GC-MS Spectrum	splash10-00kb-0940000000-aefe34765fb447090a23	Spectrum
GC-MS	L-Cysteine, 4 TMS, GC-MS Spectrum	splash10-00kb-0970000000-10a155c40ea499023052	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-00kb-0940000000-037a3a34651c3154b3b3	Spectrum
GC-MS	L-Cysteine, 4 TMS, GC-MS Spectrum	splash10-00di-9850000000-118c43e33861a6baa8d2	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-014j-0690100000-0aeb88fd507505e6b718	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-00kb-0950000000-df7e91c95b610ff21c79	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-00kb-0940000000-aefe34765fb447090a23	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-00kb-0970000000-10a155c40ea499023052	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-00kb-0940000000-037a3a34651c3154b3b3	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-0uk9-5619100000-8cb2558373966174ced3	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-00di-9850000000-118c43e33861a6baa8d2	Spectrum
GC-MS	L-Cysteine, non-derivatized, GC-MS Spectrum	splash10-0gi0-0960000000-03b2097de6f9637d29cb	Spectrum
Predicted GC-MS	L-Cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004l-9100000000-4553906a941a5e87ec97	Spectrum
Predicted GC-MS	L-Cysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-9200000000-cfaf705cd0452d428454	Spectrum
Predicted GC-MS	L-Cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cysteine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cysteine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cysteine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cysteine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cysteine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00b9-9600000000-374c5872d68662832769	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-ddbd3df6b8dbb280ffba	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-320a2c77443b80ebf733	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0089-0900000000-9dcd3d757c5cd11eb18e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-3900000000-212e081fe83ad70de0ad	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-2eb01f41c225f614db24	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-a19834eb7cb9f211fdf2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-2458f2587761e779ed93	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-9000000000-77e590f0ed26f69b31c0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-3900000000-7b1857997392b006b95f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-3900000000-bc268c27ed5706a4bbd2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-00di-0900000000-4573390bccc238e3c91b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-3900000000-212e081fe83ad70de0ad	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-3900000000-7b1857997392b006b95f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 14V, negative	splash10-001i-9000000000-5dc69d3b59bd15290aef	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-9100000000-ed3c9c47ed98679090ab	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-00di-2900000000-8bb219d17ccdf7ac0a5d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-9000000000-e623d5a27b5075c82b4d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-056r-9100000000-4e26cc13af7c878115f7	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-9600000000-4352a7b437c34c04d9f0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9200000000-7b4cd034c717561c61dd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-8f351cbca6ffed356a9b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-6900000000-51ba0df80cc33423420b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-9400000000-4aa2b707c391d5838d29	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-95c7672c7836c0fc51c9	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17561

Phenol-Explorer ID

Not Available

DrugBank ID

DB00151

HMDB ID

HMDB00574

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1018061

SuperScent ID

Not Available

Wikipedia ID

L-Cysteine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti Addisonian			DUKE
antibiotic	22582	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti cataract	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cytotoxic	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti ophthalmic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
detoxicant	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
glutathionergic			DUKE
ophthalmic antialkali			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Aspartate aminotransferase, cytoplasmic	GOT1	P17174
Aspartate aminotransferase, mitochondrial	GOT2	P00505
Glutathione synthetase	GSS	P48637
Molybdenum cofactor sulfurase	MOCOS	Q96EN8
Glutamate--cysteine ligase catalytic subunit	GCLC	P48506
Cystathionine gamma-lyase	CTH	P32929
Cysteine sulfinic acid decarboxylase	CSAD	Q9Y600
Gamma-glutamylcyclotransferase	GGCT	O75223
Phosphopantothenate--cysteine ligase	PPCS	Q9HAB8
Glutamate--cysteine ligase regulatory subunit	GCLM	P48507
Thiamine transporter 2	SLC19A3	Q9BZV2
Cysteine--tRNA ligase, cytoplasmic	CARS	P49589
Cysteine dioxygenase	CDO-1	Q16857

Pathways

Name	SMPDB Link	KEGG Link
Cysteine Metabolism	SMP00013	map00270
Glutathione Metabolism	SMP00015	map00480
Glycine and Serine Metabolism	SMP00004	map00260
Methionine Metabolism	SMP00033	map00270
Pantothenate and CoA Biosynthesis	SMP00027	map00770
Taurine and Hypotaurine Metabolism	SMP00021	map00430
Transcription/Translation	SMP00019	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sulfury	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.

L-Cysteine (FDB012678)

Structure for FDB012678 (L-Cysteine)