MiMeDB: Showing metabocard for Prolylglycine (MMDBc0000259)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:47:51 UTC

Update Date

2024-04-30 19:31:42 UTC

Metabolite ID

MMDBc0000259

Metabolite Identification

Common Name

Prolylglycine

Description

Prolylglycine is a dipeptide composed of proline and glycine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. It is found in urine (PMID: 3782411 ).

Structure

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

HEADER    PROTEIN                                 16-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-19         0                                  
HETATM    1  C   UNK     0    4665.9114667.051   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4667.2464666.282   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4668.5804667.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4669.9194666.282   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    4671.2534667.051   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    4669.9194664.741   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4665.9114668.592   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    4663.3244667.205   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    4662.0784666.299   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4662.5544664.835   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4664.0944664.835   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4664.5704666.299   0.000  0.00  0.00           C+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1                                                            
CONECT    8    9   12                                                       
CONECT    9   10    8                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8    1                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
L-Pro-gly	ChEBI
L-Prolinylglycine	ChEBI
P-G	ChEBI
PG	ChEBI
Pro-gly	ChEBI
L-Prolylglycine	HMDB
N-L-Prolylglycine	HMDB
N-Prolylglycine	HMDB
NSC 89175	HMDB
p-g Dipeptide	HMDB
PG Dipeptide	HMDB
Proline glycine dipeptide	HMDB
Proline-glycine dipeptide	HMDB
Prolyl-glycine	HMDB
Prolylglycine	ChEBI

Molecular Formula

C₇H₁₂N₂O₃

Average Mass

172.1818

Monoisotopic Mass

172.08479226

IUPAC Name

2-{[(2S)-pyrrolidin-2-yl]formamido}acetic acid

Traditional Name

Pro-Gly

CAS Registry Number

2578-57-6

SMILES

OC(=O)CNC(=O)[C@@H]1CCCN1

InChI Identifier

InChI=1S/C7H12N2O3/c10-6(11)4-9-7(12)5-2-1-3-8-5/h5,8H,1-4H2,(H,9,12)(H,10,11)/t5-/m0/s1

InChI Key

RNKSNIBMTUYWSH-YFKPBYRVSA-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
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Amine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:61695 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.91 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	9.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	40.87 m³·mol⁻¹	ChemAxon
Polarizability	16.79 Å³	ChemAxon
Number of Rings	1	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
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0006-2900000000-89799a6272194efe9d08	2014-06-16	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-6900000000-24972ffd24ebd1448086	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-f5860fa130816fb7c463	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9000000000-97f3a107affd584af871	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-1add648393301d0feba1	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-7900000000-b60a3bc21d3dd4103fff	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-bc534a481231b926bd6c	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006t-9000000000-2e9e8efc641c3dfd18bb	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-8f982a38658d827f57dc	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-98be7b4ea7f829765085	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-6445b0236efd5117342d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00r2-9100000000-55c1fb3d336df678f0bd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-834448a1543365041616	2021-09-24	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
Urine

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	Firmicutes	3	Human stool; Human ; Human feces; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.31	0.16	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	10219662
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

HMDB0011178

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00011257

Chemspider ID

4932143

KEGG Compound ID

Not Available

BioCyc ID

CPD0-2182

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6426709

PDB ID

Not Available

ChEBI ID

61695

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Jandke J, Spiteller G: Dipeptide analysis in human urine. J Chromatogr. 1986 Oct 31;382:39-45. doi: 10.1016/s0378-4347(00)83502-1. [PubMed:3782411 ]

Showing metabocard for Prolylglycine (MMDBc0000259)

MOL for #<Metabolite:0x00007fdb545f7a08>

3D MOL for #<Metabolite:0x00007fdb545f7a08>

3D SDF for #<Metabolite:0x00007fdb545f7a08>

3D-SDF for #<Metabolite:0x00007fdb545f7a08>

PDB for #<Metabolite:0x00007fdb545f7a08>

3D PDB for #<Metabolite:0x00007fdb545f7a08>

SMILES for #<Metabolite:0x00007fdb545f7a08>

INCHI for #<Metabolite:0x00007fdb545f7a08>

Structure for #<Metabolite:0x00007fdb545f7a08>

3D Structure for #<Metabolite:0x00007fdb545f7a08>