MiMeDB: Showing metabocard for Glycylvaline (MMDBc0000468)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:27 UTC

Update Date

2024-04-30 19:32:30 UTC

Metabolite ID

MMDBc0000468

Metabolite Identification

Common Name

Glycylvaline

Description

Glycylvaline is a dipeptide composed of glycine and valine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Structure

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

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    8643.4018644.838   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8643.4018643.300   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8644.7348642.528   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8646.0708643.300   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8647.4028642.528   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0    8644.7348640.988   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8642.0678645.608   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8640.7338644.838   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8642.0678647.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8644.7348645.608   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8646.0708644.838   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8644.7348647.148   0.000  0.00  0.00           O+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
Gly-L-val	ChEBI
Glycyl-valine	ChEBI
GV	ChEBI
Glycylvaline, (L)-isomer	HMDB
Glycylvaline, (D)-isomer	HMDB
Gly-val	HMDB
g-V Dipeptide	HMDB
GV Dipeptide	HMDB
Glycine valine dipeptide	HMDB
Glycine-valine dipeptide	HMDB
Glycyl-L-valine	HMDB
N-Glycyl-L-valine	HMDB
N-Glycylvaline	HMDB
Glycylvaline	ChEBI

Molecular Formula

C₇H₁₄N₂O₃

Average Mass

174.2

Monoisotopic Mass

174.100442319

IUPAC Name

(2S)-2-(2-aminoacetamido)-3-methylbutanoic acid

Traditional Name

gly-val

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](NC(=O)CN)C(O)=O

InChI Identifier

InChI=1S/C7H14N2O3/c1-4(2)6(7(11)12)9-5(10)3-8/h4,6H,3,8H2,1-2H3,(H,9,10)(H,11,12)/t6-/m0/s1

InChI Key

STKYPAFSDFAEPH-LURJTMIESA-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 or derivatives
N-acyl-alpha-amino acid
Valine or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73922 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	34.2 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.1	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Acidic)	3.81	ChemAxon
pKa (Strongest Basic)	8.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	42.3 m³·mol⁻¹	ChemAxon
Polarizability	17.59 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	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-22aab51edd782feb3b80	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-9000000000-9d3bc041813a172a126c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-9000000000-b8ca877ca975c7d18478	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0100-6900000000-04daf0e06504ac6056aa	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0100-5900000000-80aa0418207f00d55130	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-a33d201b189787c83ea7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-004i-0900000000-adb8ea2796cdb2e0adb5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0ab9-9000000000-7079c0a3dd91959e413e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-016r-0900000000-e28cbd287a513576fcc0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-5900000000-783be20fde47c765f0d8	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-60097e54fbfdc1ecad0e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-4900000000-85f19cdd121d294d41a0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-50e48ea605aef64385e3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-2c6b23894c901c1ddef1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9200000000-b4828c40b3415069f101	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-61dea7058a50b0bcf64c	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Metabolic Reactions

Not Available

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	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	2	Human ; Human urine; Human feces; Human stool; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	1	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	6	Human stool; Human ; Human feces; Human urine; Human sputum; Human saliva; Human subgingival plaque; Human vaginal fluid; Human supragingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0028854

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111886

KNApSAcK ID

Not Available

Chemspider ID

2006926

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2724807

PDB ID

Not Available

ChEBI ID

73922

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kline EL, Brown CS, Umbarger HE: Effect of a leu-linked mutation on the valine sensitivity of acetohydroxy acid synthase activity in Escherichia coli. J Bacteriol. 1975 Feb;121(2):491-6. doi: 10.1128/jb.121.2.491-496.1975. [PubMed:1089631 ]
Steininger R, Karner J, Roth E, Langer K: Infusion of dipeptides as nutritional substrates for glutamine, tyrosine, and branched-chain amino acids in patients with acute pancreatitis. Metabolism. 1989 Aug;38(8 Suppl 1):78-81. doi: 10.1016/0026-0495(89)90147-9. [PubMed:2503685 ]
Valenkevich LN: [Clinical importance of the determination of intestinal dipeptidase and enterokinase activity in patients with chronic enteritis]. Ter Arkh. 1987;59(11):88-90. [PubMed:3481658 ]
De Felice M, Guardiola J, Lamberti A, Iaccarino M: Escherichia coli K-12 mutants altered in the transport systems for oligo- and dipeptides. J Bacteriol. 1973 Nov;116(2):751-6. doi: 10.1128/jb.116.2.751-756.1973. [PubMed:4126826 ]
Guardiola J, De Felice M, Klopotowski T, Iaccarino M: Mutations affecting the different transport systems for isoleucine, leucine, and valine in Escherichia coli K-12. J Bacteriol. 1974 Feb;117(2):393-405. doi: 10.1128/jb.117.2.393-405.1974. [PubMed:4590465 ]
Huckle KR, Hutson DH, Millburn P: Species differences in the metabolism of 3-phenoxybenzoic acid. Drug Metab Dispos. 1981 Jul-Aug;9(4):352-9. [PubMed:6114835 ]
SHELTON DC, NUTTER WE: UPTAKE OF VALINE AND GLYCYLVALINE BY LEUCONOSTOC MESENTEROIDES. J Bacteriol. 1964 Oct;88:1175-84. doi: 10.1128/jb.88.4.1175-1184.1964. [PubMed:14219035 ]
Nath M, Pokharia S, Eng G, Song X, Kumar A: New triorganotin(IV) derivatives of dipeptides as anti-inflammatory-antimicrobial agents. Eur J Med Chem. 2005 Mar;40(3):289-98. doi: 10.1016/j.ejmech.2004.11.001. Epub 2005 Jan 4. [PubMed:15725498 ]
Zhang CX, Tong HB, Yan CG: First soluble multipolymer MPEG-supported liquid-phase convergent synthesis of tripeptide Fmoc-GlyVal-GlyOH. J Comb Chem. 2007 Nov-Dec;9(6):924-5. doi: 10.1021/cc700156r. Epub 2007 Oct 31. [PubMed:17970597 ]

Showing metabocard for Glycylvaline (MMDBc0000468)

MOL for #<Metabolite:0x00007fdaf2904190>

3D MOL for #<Metabolite:0x00007fdaf2904190>

3D SDF for #<Metabolite:0x00007fdaf2904190>

3D-SDF for #<Metabolite:0x00007fdaf2904190>

PDB for #<Metabolite:0x00007fdaf2904190>

3D PDB for #<Metabolite:0x00007fdaf2904190>

SMILES for #<Metabolite:0x00007fdaf2904190>

INCHI for #<Metabolite:0x00007fdaf2904190>

Structure for #<Metabolite:0x00007fdaf2904190>

3D Structure for #<Metabolite:0x00007fdaf2904190>