Cannabis Compound Database: Showing Compound Card for Cysteinylglycine (CDB004797)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (9) Show 12 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:37:45 UTC

Updated at

2020-11-18 16:38:42 UTC

CannabisDB ID

CDB004797

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Cysteinylglycine

Description

Cysteinylglycine, also known as CG or cys-gly, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. As this dipeptidase also hydrolyzes the glutathione metabolite cysteinylglycine, the therapeutic association of imipenem and cilastatin causes plasma levels of cysteinylglycine to increase significantly, while cysteine levels are decreased and homocysteine levels are unaffected. Cysteinylglycine is a naturally occurring dipeptide composed of cysteine and glycine. Imipenem (thienamycin formamidine) is a broad-spectrum beta-lactam antibiotic, always used in combination with cilastatin in order to avoid the premature breakdown of imipenem by renal tubular dipeptidase. It is derived from the breakdown of glutathione (a tripeptide). Cysteinylglycine is a very strong basic compound (based on its pKa). Cysteinylglycine exists in all living species, ranging from bacteria to humans. The damage process seems to be related to an overproduction of oxygen reactive species inducing an oxidative perturbation with an increase in some oxidized forms (disulfides and protein mixed disulfides) and a decrease in free thiols (PMID: 15895891 ). Outside of the human body, Cysteinylglycine has been detected, but not quantified in, several different foods, such as garlics, sweet rowanberries, butternut squash, common oregano, and pepper (c. frutescens). This could make cysteinylglycine a potential biomarker for the consumption of these foods. Cysteinylglycine, with regard to humans, has been linked to the inborn metabolic disorder phenylketonuria. Therefore, antibiotic treatment using imipenem-cilastatin induces important metabolic changes that should not remain unrecognized (PMID: 15843241 ). In plasma, cysteinylglycine is in a reduced, oxidized, and protein-bound form (aminothiol) and interacts via redox and disulphide exchange reactions in a dynamic system referred to as redox thiol status (PMID: 8642471 ). The detrimental effect on embryo quality of a high homocysteine (Hcy) concentration in the ejaculate and in the follicular fluid is intriguing and may suggest that Hcy is inversely associated with fertility outcome (PMID: 16556671 ). Cysteinylglycine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CG	ChEBI
Cys-gly	ChEBI
N-L-Cysteinylglycine	ChEBI
L-Cysteinylglycine	Kegg
N-Cysteinyl glycine	HMDB
N-Cysteinyl-glycine	HMDB
N-L-Cysteinyl-glycine	HMDB
Cysteinyl-glycine	HMDB
C-g Dipeptide	HMDB
CG Dipeptide	HMDB
Cysteine glycine dipeptide	HMDB
Cysteine-glycine dipeptide	HMDB
L-Cys-gly	HMDB
N-Cysteinylglycine	HMDB
Cysteinylglycine	ChEBI

Chemical Formula

C₅H₁₀N₂O₃S

Average Molecular Weight

178.21

Monoisotopic Molecular Weight

178.0412

IUPAC Name

2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid

Traditional Name

Cys-Gly

CAS Registry Number

19246-18-5

SMILES

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

InChI Identifier

InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)/t3-/m0/s1

InChI Key

ZUKPVRWZDMRIEO-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid or derivatives
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Alkylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:4047 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.6	ALOGPS
logP	-3.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	8.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.03 m³·mol⁻¹	ChemAxon
Polarizability	16.97 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

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Cysteinylglycine, 3 TMS, GC-MS Spectrum	splash10-00di-2980000000-043097e8f1f3f47ff51f	Spectrum
GC-MS	Cysteinylglycine, non-derivatized, GC-MS Spectrum	splash10-00di-9440000000-ff8b27f3afc92193d83a	Spectrum
GC-MS	Cysteinylglycine, non-derivatized, GC-MS Spectrum	splash10-00di-2980000000-043097e8f1f3f47ff51f	Spectrum
Predicted GC-MS	Cysteinylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-9200000000-bae23059b39c80a574a5	Spectrum
Predicted GC-MS	Cysteinylglycine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006t-8920000000-1b3a6e358d6996916b0e	Spectrum
Predicted GC-MS	Cysteinylglycine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cysteinylglycine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cysteinylglycine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cysteinylglycine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cysteinylglycine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cysteinylglycine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cysteinylglycine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cysteinylglycine, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-9700000000-6fba6043a24b724b037e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-50e069074067c9f120bd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9100000000-ab3327c5b13829ea6d35	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9700000000-9021340a904a56f317cc	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-5900000000-b9a1082799c427caf10b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9200000000-2b99992e97c6ecb4567b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6u-9000000000-a8b591f7522fe16637fb	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-0173b5cf52bb61095c3a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00gl-7900000000-f8dc26c3e8b8ec327fc4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kh9-9100000000-410b0cc1b5e3f850b505	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0096-5900000000-55967cd7162376aa6fa2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9200000000-5aab410f2c44502defce	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-e0ae26ebba3eeba905da	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-9400000000-1878c834f39272d5af42	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9100000000-0899c0bce2addb667ccb	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-05f619b00f6286d67d21	2021-09-23	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glutathione Metabolism
Glutathione Synthetase Deficiency		Not Available
5-Oxoprolinuria		Not Available
Gamma-Glutamyltransferase Deficiency		Not Available
5-oxoprolinase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aminopeptidase N	ANPEP		P15144	details
Gamma-glutamyltranspeptidase 1	GGT1	22q11.23	P19440	details
Gamma-glutamyltransferase 7	GGT7	20q11.22	Q9UJ14	details
Cytosol aminopeptidase	LAP3		P28838	details
Gamma-glutamyltransferase 6	GGT6	17p13.2	Q6P531	details
GGT7 protein	GGT7	20q11.22	A0PJJ9	details
Gamma-glutamyltransferase 5	GGT5	22q11.23	P36269	details
Gamma-glutamyltranspeptidase 2	GGT2		P36268	details
Putative gamma-glutamyltranspeptidase 3	GGT3P		A6NGU5	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aminopeptidase N	ANPEP		P15144	details
Cytosol aminopeptidase	LAP3		P28838	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aminopeptidase N	ANPEP		P15144	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000078

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021891

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

5134

PubChem Compound

439498

PDB ID

Not Available

ChEBI ID

4047

References

General References

Giustarini D, Lorenzini S, Rossi R, Chindamo D, Di Simplicio P, Marcolongo R: Altered thiol pattern in plasma of subjects affected by rheumatoid arthritis. Clin Exp Rheumatol. 2005 Mar-Apr;23(2):205-12. [PubMed:15895891 ]
Badiou S, Bellet H, Lehmann S, Cristol JP, Jaber S: Elevated plasma cysteinylglycine levels caused by cilastatin-associated antibiotic treatment. Clin Chem Lab Med. 2005;43(3):332-4. doi: 10.1515/CCLM.2005.057. [PubMed:15843241 ]
Ueland PM, Mansoor MA, Guttormsen AB, Muller F, Aukrust P, Refsum H, Svardal AM: Reduced, oxidized and protein-bound forms of homocysteine and other aminothiols in plasma comprise the redox thiol status--a possible element of the extracellular antioxidant defense system. J Nutr. 1996 Apr;126(4 Suppl):1281S-4S. doi: 10.1093/jn/126.suppl_4.1281S. [PubMed:8642471 ]
Ebisch IM, Peters WH, Thomas CM, Wetzels AM, Peer PG, Steegers-Theunissen RP: Homocysteine, glutathione and related thiols affect fertility parameters in the (sub)fertile couple. Hum Reprod. 2006 Jul;21(7):1725-33. doi: 10.1093/humrep/del081. Epub 2006 Mar 23. [PubMed:16556671 ]

Only showing the first 10 proteins. There are 12 proteins in total.

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Enzymes

Enzyme Details

1. Aminopeptidase N

General function:: Involved in proteolysis
Specific function:: Broad specificity aminopeptidase. Plays a role in the final digestion of peptides generated from hydrolysis of proteins by gastric and pancreatic proteases. May play a critical role in the pathogenesis of cholesterol gallstone disease. May be involved in the metabolism of regulatory peptides of diverse cell types, responsible for the processing of peptide hormones, such as angiotensin III and IV, neuropeptides, and chemokines. Found to cleave antigen peptides bound to major histocompatibility complex class II molecules of presenting cells and to degrade neurotransmitters at synaptic junctions. Is also implicated as a regulator of IL-8 bioavailability in the endometrium, and therefore may contribute to the regulation of angiogenesis. Is used as a marker for acute myeloid leukemia and plays a role in tumor invasion. In case of human coronavirus 229E (HCoV-229E) infection, serves as receptor for HCoV-229E spike glycoprotein. Mediates as well human cytomegalovirus (HCMV) infection.
Gene Name:: ANPEP
Uniprot ID:: P15144
Molecular weight:: Not Available

Enzyme Details

2. Gamma-glutamyltranspeptidase 1

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:: GGT1
Uniprot ID:: P19440
Molecular weight:: 61409.67

Enzyme Details

3. Gamma-glutamyltransferase 7

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves glutathione conjugates (By similarity).
Gene Name:: GGT7
Uniprot ID:: Q9UJ14
Molecular weight:: 70466.015

Enzyme Details

4. Cytosol aminopeptidase

General function:: Involved in aminopeptidase activity
Specific function:: Presumably involved in the processing and regular turnover of intracellular proteins. Catalyzes the removal of unsubstituted N-terminal amino acids from various peptides.
Gene Name:: LAP3
Uniprot ID:: P28838
Molecular weight:: Not Available

Enzyme Details

5. Gamma-glutamyltransferase 6

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves glutathione conjugates (By similarity).
Gene Name:: GGT6
Uniprot ID:: Q6P531
Molecular weight:: 50508.83

Enzyme Details

6. GGT7 protein

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Not Available
Gene Name:: GGT7
Uniprot ID:: A0PJJ9
Molecular weight:: 62565.3

Enzyme Details

7. Gamma-glutamyltransferase 5

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:: GGT5
Uniprot ID:: P36269
Molecular weight:: 62331.75

Enzyme Details

8. Gamma-glutamyltranspeptidase 2

General function:: Not Available
Specific function:: Initiates extracellular glutathione (GSH) breakdown; catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors (By similarity).
Gene Name:: GGT2
Uniprot ID:: P36268
Molecular weight:: Not Available

Enzyme Details

9. Putative gamma-glutamyltranspeptidase 3

General function:: Not Available
Specific function:: Initiates extracellular glutathione (GSH) breakdown; catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors (By similarity).
Gene Name:: GGT3P
Uniprot ID:: A6NGU5
Molecular weight:: Not Available

Only showing the first 10 proteins. There are 12 proteins in total.

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Showing Compound Card for Cysteinylglycine (CDB004797)

Structure for CDB004797 (Cysteinylglycine)

Enzymes