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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:06 UTC

HMDB ID

HMDB0000721

Secondary Accession Numbers

HMDB00721

Metabolite Identification

Common Name

Glycylproline

Description

Glycylproline is a dipeptide composed of glycine and proline, and is an end product of collagen metabolism that is further cleaved by prolidase (EC 3.4.13.9). The resulting proline molecules are recycled into collagen or other proteins. Prolidase deficiency is a rare autosomal recessive disease characterized by chronic ulcerative dermatitis, mental retardation, frequent infections, and massive urinary excretion of iminodipeptides. Patients with this disease have reportedly decreased prolidase enzyme activity against glycylproline (Gly-Pro). The enzyme's activity against other substrates is not as affected. Some patients with prolidase deficiency have a marked urinary excretion of glycylproline. Patients with pressure sores contain significantly more urinary glycylproline than the control (PMID: 16009141 , 7629169 , 1536787 , 10582130 ).

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    4665.9154668.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4664.5804669.015   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4663.2344668.269   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0    4667.2504669.015   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4668.7644666.701   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4670.0994665.933   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4668.7644668.242   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    4665.8824666.683   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    4664.6364665.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4665.1124664.313   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4666.6524664.313   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4667.1284665.777   0.000  0.00  0.00           C+0
CONECT    1    2    4    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1                                                            
CONECT    5    6    7   12                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    9   12    1                                                  
CONECT    9   10    8                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8    5                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(Aminoacetyl)proline	ChEBI
1-Glycylproline	ChEBI
Gly-L-pro	ChEBI
GP	ChEBI
N-Glycyl-L-proline	ChEBI
N-Glycylproline	ChEBI
Glycyl-L-proline	HMDB
(S)-1-(2-Aminoacetyl)pyrrolidine-2-carboxylic acid	HMDB
1-Glycyl-L-proline	HMDB
g-p Dipeptide	HMDB
GP Dipeptide	HMDB
Gly-pro	HMDB
Glycine proline dipeptide	HMDB
Glycine-proline dipeptide	HMDB
Glycyl-proline	HMDB
NSC 97929	HMDB
Glycylproline	ChEBI

Chemical Formula

C₇H₁₂N₂O₃

Average Molecular Weight

172.1818

Monoisotopic Molecular Weight

172.08479226

IUPAC Name

(2S)-1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid

Traditional Name

glycylproline

CAS Registry Number

704-15-4

SMILES

NCC(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)/t5-/m0/s1

InChI Key

KZNQNBZMBZJQJO-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-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary aliphatic amine
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:70744 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	155 - 158 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	134.59	30932474
[M+H]+	MetCCS_train_pos	136.373	30932474
[M-H]-	Not Available	134.59	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000029
[M+H]+	Not Available	136.412	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000029

Predicted Molecular Properties

Property	Value	Source
Water Solubility	279 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.7	ChemAxon
logS	0.21	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	8.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.99 m³·mol⁻¹	ChemAxon
Polarizability	16.75 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	133.025	30932474
DeepCCS	[M-H]-	129.197	30932474
DeepCCS	[M-2H]-	166.721	30932474
DeepCCS	[M+Na]+	142.26	30932474
AllCCS	[M+H]+	136.4	32859911
AllCCS	[M+H-H2O]+	132.2	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	133.1	32859911
AllCCS	[M+Na-2H]-	134.1	32859911
AllCCS	[M+HCOO]-	135.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.47 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8165 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	338.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	513.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	263.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	248.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	242.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	766.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	558.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	43.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	723.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	669.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	458.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	303.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycylproline	NCC(=O)N1CCC[C@H]1C(O)=O	2350.3	Standard polar	33892256
Glycylproline	NCC(=O)N1CCC[C@H]1C(O)=O	1819.6	Standard non polar	33892256
Glycylproline	NCC(=O)N1CCC[C@H]1C(O)=O	1844.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycylproline,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CN	1711.6	Semi standard non polar	33892256
Glycylproline,1TMS,isomer #2	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)O	1790.5	Semi standard non polar	33892256
Glycylproline,2TMS,isomer #1	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1808.0	Semi standard non polar	33892256
Glycylproline,2TMS,isomer #1	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1831.4	Standard non polar	33892256
Glycylproline,2TMS,isomer #1	C[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2342.3	Standard polar	33892256
Glycylproline,2TMS,isomer #2	C[Si](C)(C)N(CC(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	1922.0	Semi standard non polar	33892256
Glycylproline,2TMS,isomer #2	C[Si](C)(C)N(CC(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	1935.1	Standard non polar	33892256
Glycylproline,2TMS,isomer #2	C[Si](C)(C)N(CC(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2542.5	Standard polar	33892256
Glycylproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	1974.7	Semi standard non polar	33892256
Glycylproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	1970.0	Standard non polar	33892256
Glycylproline,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C)[Si](C)(C)C	2166.4	Standard polar	33892256
Glycylproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CN	1943.3	Semi standard non polar	33892256
Glycylproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)O	2014.2	Semi standard non polar	33892256
Glycylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2252.2	Semi standard non polar	33892256
Glycylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2274.2	Standard non polar	33892256
Glycylproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2474.4	Standard polar	33892256
Glycylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2336.3	Semi standard non polar	33892256
Glycylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2352.5	Standard non polar	33892256
Glycylproline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	2597.1	Standard polar	33892256
Glycylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2571.0	Semi standard non polar	33892256
Glycylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2586.7	Standard non polar	33892256
Glycylproline,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2469.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Glycylproline GC-MS (3 TMS)	splash10-00di-2901000000-1b9ae10ce7fa6c3ddfba	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylproline GC-EI-TOF (Non-derivatized)	splash10-00di-1901000000-f37ccc8ccf214e97d6b6	2019-03-08	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylproline GC-EI-TOF (Non-derivatized)	splash10-00di-1901000000-f37ccc8ccf214e97d6b6	2019-03-08	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylproline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylproline GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylproline GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylproline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylproline GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-1900000000-9da065ddc26b31b36592	2019-03-08	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-01b9-5900000000-583b4cb589c2ec738f36	2019-03-08	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00di-9000000000-7bdaea720328b0c3851e	2019-03-08	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 30V, Positive-QTOF	splash10-00di-9000000000-524b721e73f3f887c681	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 40V, Positive-QTOF	splash10-00di-9000000000-2940e6237c21dbb5beee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 10V, Positive-QTOF	splash10-00xr-7900000000-2c485a901dc7d65e0c7a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 0V, Positive-QTOF	splash10-00di-6900000000-0809cb7a542853d1a964	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 30V, Positive-QTOF	splash10-00fv-9000000000-0f3f6db9502dba42c40a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 0V, Positive-QTOF	splash10-00di-0900000000-691af9a68cb0bc804261	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 20V, Positive-QTOF	splash10-00di-9300000000-f89829e245592af7832e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 10V, Positive-QTOF	splash10-01b9-2900000000-07189ee8865b832b5d35	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 10V, Positive-QTOF	splash10-01b9-2900000000-5da22ef9598476d82c7f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylproline 30V, Positive-QTOF	splash10-00di-9100000000-e5f29a91a023b15855ec	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 10V, Positive-QTOF	splash10-05fr-1900000000-6987035260ca993cd43e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 20V, Positive-QTOF	splash10-0ac0-9600000000-c74cee61fd2ec534af77	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 40V, Positive-QTOF	splash10-014l-9000000000-48d0c933c8b6f78e839f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 10V, Negative-QTOF	splash10-00fr-0900000000-55b1206a1419a41e86ff	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 20V, Negative-QTOF	splash10-00b9-3900000000-6739642d8410a9a177ed	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 40V, Negative-QTOF	splash10-00di-9200000000-16170c56a5433313b0aa	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 10V, Negative-QTOF	splash10-03k9-0900000000-c96e09599210c8ad1286	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 20V, Negative-QTOF	splash10-03di-5900000000-ee573e16cf640a002b33	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 40V, Negative-QTOF	splash10-0006-9200000000-04634bf9835152674496	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 10V, Positive-QTOF	splash10-01b9-4900000000-47d2ea68a762ed22c884	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 20V, Positive-QTOF	splash10-00xs-9400000000-87dbef1e712c254ed5aa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylproline 40V, Positive-QTOF	splash10-00di-9000000000-ce80042f9a9ea592870e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2019-03-08	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	0.4 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21388201	details
Urine	Detected and Quantified	61.403 +/- 24.479 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0 - 16.17 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 16.17 umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 16.17 umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 16.17 umol/mmol creatinine	Children (1 - 2 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 16.17 umol/mmol creatinine	Children (2 - 4 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 16.17 umol/mmol creatinine	Children (4 - 13 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 16.17 umol/mmol creatinine	Adolescent (13 - 21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 16.17 umol/mmol creatinine	Adult (>21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	1.4-2.8 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	1.1-2.0 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.23 +/- 0.04 uM	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.086 +/- 0.016 uM	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	590.8 +/- 81.14 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Prolidase deficiency	2026685 16120410	details
Urine	Detected and Quantified	0.0087 +/- 0.0016 umol/mmol creatinine	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
Urine	Detected and Quantified	46.339 +/- 42.779 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Alzheimer's disease
Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Prolidase deficiency
Barshop BA: Metabolomic approaches to mitochondrial disease: correlation of urine organic acids. Mitochondrion. 2004 Sep;4(5-6):521-7. Epub 2004 Sep 30. [PubMed:16120410 ] Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

104300 (Alzheimer's disease)
114500 (Colorectal cancer)
170100 (Prolidase deficiency)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022202

KNApSAcK ID

Not Available

Chemspider ID

2282246

KEGG Compound ID

Not Available

BioCyc ID

CPD-10814

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3013625

PDB ID

Not Available

ChEBI ID

70744

Food Biomarker Ontology

Not Available

VMH ID

GLYPRO

MarkerDB ID

MDB00000236

Good Scents ID

Not Available

References

Synthesis Reference

Maruyama, Susumu; Ichimura, Toshiaki; Otsuka, Tatsuo; Yamashita, Eiichi. Long-lasting antihypertensive agents and glycylproline manufactured from collagen and/or gelatin. Jpn. Kokai Tokkyo Koho (2005), 10 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Barshop BA: Metabolomic approaches to mitochondrial disease: correlation of urine organic acids. Mitochondrion. 2004 Sep;4(5-6):521-7. Epub 2004 Sep 30. [PubMed:16120410 ]
Krepela E, Kasafirek E, Vicar J, Kraml J: An assay of dipeptidyl peptidase IV activity in human serum and serum of pregnant women with glycyl-L-proline-1-naphthylamide and other glycyl-L-proline-arylamides as substrates. Physiol Bohemoslov. 1983;32(4):334-45. [PubMed:6353449 ]
Liu G, Nakayama K, Sagara Y, Awata S, Yamashita K, Manabe M, Kodama H: Characterization of prolidase activity in erythrocytes from a patient with prolidase deficiency: comparison with prolidase I and II purified from normal human erythrocytes. Clin Biochem. 2005 Jul;38(7):625-31. [PubMed:16009141 ]
Mock WL, Liu Y: Hydrolysis of picolinylprolines by prolidase. A general mechanism for the dual-metal ion containing aminopeptidases. J Biol Chem. 1995 Aug 4;270(31):18437-46. [PubMed:7629169 ]
Berardesca E, Fideli D, Bellosta M, Dyne KM, Zanaboni G, Cetta G: Blood transfusions in the therapy of a case of prolidase deficiency. Br J Dermatol. 1992 Feb;126(2):193-5. [PubMed:1536787 ]
Le J, Perier C, Peyroche S, Rascle F, Blanchon MA, Gonthier R, Frey J, Chamson A: Urine glycyl-L-proline increase and skin trophicity. Amino Acids. 1999;17(3):315-22. [PubMed:10582130 ]

Enzymes

Enzyme Details

1. Xaa-Pro dipeptidase

General function:: Involved in cellular process
Specific function:: Splits dipeptides with a prolyl or hydroxyprolyl residue in the C-terminal position. Plays an important role in collagen metabolism because the high level of iminoacids in collagen
Gene Name:: PEPD
Uniprot ID:: P12955
Molecular weight:: 54547.8

References

Yuan J, Li T, Yin XB, Guo L, Jiang X, Jin W, Yang X, Wang E: Characterization of prolidase activity using capillary electrophoresis with tris(2,2'-bipyridyl)ruthenium(II) electrochemiluminescence detection and application to evaluate collagen degradation in diabetes mellitus. Anal Chem. 2006 May 1;78(9):2934-8. [PubMed:16642978 ]

Showing metabocard for Glycylproline (HMDB0000721)

MOL for HMDB0000721 (Glycylproline)

3D MOL for HMDB0000721 (Glycylproline)

3D SDF for HMDB0000721 (Glycylproline)

3D-SDF for HMDB0000721 (Glycylproline)

PDB for HMDB0000721 (Glycylproline)

3D PDB for HMDB0000721 (Glycylproline)

SMILES for HMDB0000721 (Glycylproline)

INCHI for HMDB0000721 (Glycylproline)

Structure for HMDB0000721 (Glycylproline)

3D Structure for HMDB0000721 (Glycylproline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References