MiMeDB: Showing metabocard for D-Cysteine (MMDBc0000243)

Microbial

Human

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:41:05 UTC

Update Date

2024-10-11 03:58:24 UTC

Metabolite ID

MMDBc0000243

Metabolite Identification

Common Name

D-Cysteine

Description

D-Cysteine is a naturally occurring enantiomer of L-Cysteine. It is a non-proteogenic sulfur-containing amino acid. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder − cystine was first isolated from kidney stones. (wikipedia) D-cysteine can be generated from L-cysteine via cysteine racemase. D-Cysteine is known to be toxic to bacteria and several bacteria (and plants) have developed and enzyme called D-cysteine desulfhydrase (EC 4.1.99.4). This enzyme decomposes D-cysteine into pyruvate, H2S, and NH3. (PMID: 15720402 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-3-mercaptopropanoic acid	ChEBI
(2S)-2-Amino-3-sulfanylpropanoic acid	ChEBI
(S)-2-Amino-3-mercaptopropanoic acid	ChEBI
D-Amino-3-mercaptopropionic acid	ChEBI
D-Cystein	ChEBI
D-Zystein	ChEBI
DCY	ChEBI
(2S)-2-Amino-3-mercaptopropanoate	Generator
(2S)-2-Amino-3-sulfanylpropanoate	Generator
(2S)-2-Amino-3-sulphanylpropanoate	Generator
(2S)-2-Amino-3-sulphanylpropanoic acid	Generator
(S)-2-Amino-3-mercaptopropanoate	Generator
D-Amino-3-mercaptopropionate	Generator
Cysteine	MeSH, HMDB
Half cystine	MeSH, HMDB
Cysteine hydrochloride	MeSH, HMDB
Half-cystine	MeSH, HMDB
L-Cysteine	MeSH, HMDB
L Cysteine	MeSH, HMDB
Zinc cysteinate	MeSH, HMDB

Molecular Formula

C₃H₇NO₂S

Average Mass

121.15

Monoisotopic Mass

121.019749643

IUPAC Name

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

Traditional Name

L cysteine

CAS Registry Number

921-01-7

SMILES

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

InChI Identifier

InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1

InChI Key

XUJNEKJLAYXESH-UWTATZPHSA-N

Chemical Taxonomy

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
D-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

D-alpha-amino acid (CHEBI:16375 )
cysteine (CHEBI:16375 )
Other amino acids (C00793 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	11.4 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9100000000-4553906a941a5e87ec97	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-004i-9200000000-cfaf705cd0452d428454	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-056r-9300000000-ed3d829a54e4ac06325d	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0a4i-9000000000-224425097c9b1883d266	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0a4i-9000000000-39cb21d5fd8f893ba8fd	2012-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-9600000000-4352a7b437c34c04d9f0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9200000000-7b4cd034c717561c61dd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-8f351cbca6ffed356a9b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-6900000000-51ba0df80cc33423420b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-9400000000-4aa2b707c391d5838d29	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-95c7672c7836c0fc51c9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-8900000000-c05a34dee4bebd8457da	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-9200000000-9d710aa92c54b66150d6	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-e5d74af54cd557ea9df0	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f349eed712afbbc2670a	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0026124	D-Cysteine	N-Acetyl-D-cysteine	D-amino-acid N-acetyltransferase HPA3	Acetylation	RHEA	34755880
MMDBr0026130	L-Cysteine	D-Cysteine	Broad substrate specificity amino-acid racemase	Racemization	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	5	Human feces; Human stool; Human saliva; Human ; Human urine	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Fibrobacteres	1		Microbial culture
Bacteria/Eubacteria	Firmicutes	6	Human ; Human feces; Goat feces; Sheep feces	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1		Microbial culture
Bacteria/Eubacteria	Fusobacteria	1	Human mucosa; Human supragingival plaque; Human ; Human urine; Human feces; Human saliva; Human subgingival plaque	Microbial culture
Bacteria/Eubacteria	Proteobacteria	57	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction
Bacteria	Proteobacteria	3	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Saliva	Detected and Quantified	8.643	2.11			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5

External Links

HMDB ID

HMDB0003417

DrugBank ID

DB03201

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cysteine

METLIN ID

Not Available

PubChem Compound

92851

PDB ID

Not Available

ChEBI ID

16375

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Tsukamoto S, Kanegae T, Nagoya T, Shimamura M, Mieda Y, Nomura M, Hojo K, Okubo H: Effects of amino acids on acute alcohol intoxication in mice--concentrations of ethanol, acetaldehyde, acetate and acetone in blood and tissues. Arukoru Kenkyuto Yakubutsu Ison. 1990 Oct;25(5):429-40. [PubMed:2275637 ]
Riemenschneider A, Wegele R, Schmidt A, Papenbrock J: Isolation and characterization of a D-cysteine desulfhydrase protein from Arabidopsis thaliana. FEBS J. 2005 Mar;272(5):1291-304. doi: 10.1111/j.1742-4658.2005.04567.x. [PubMed:15720402 ]

Showing metabocard for D-Cysteine (MMDBc0000243)

MOL for #<Metabolite:0x00007fade8a48c68>

3D MOL for #<Metabolite:0x00007fade8a48c68>

3D SDF for #<Metabolite:0x00007fade8a48c68>

3D-SDF for #<Metabolite:0x00007fade8a48c68>

PDB for #<Metabolite:0x00007fade8a48c68>

3D PDB for #<Metabolite:0x00007fade8a48c68>

SMILES for #<Metabolite:0x00007fade8a48c68>

INCHI for #<Metabolite:0x00007fade8a48c68>

Structure for #<Metabolite:0x00007fade8a48c68>

3D Structure for #<Metabolite:0x00007fade8a48c68>