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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 21:09:19 UTC

Update Date

2022-09-22 18:35:15 UTC

HMDB ID

HMDB0341432

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Threoninyl-Proline

Description

Threoninyl-Proline, also known as T-p dipeptide or THR-pro, 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. Threoninyl-Proline is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. Threoninyl-Proline is a dipeptide composed of threonine and proline. 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.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02051311312D          

 15 15  0  0  0  0            999 V2000
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -0.4747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    0.0352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341432

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)C(N)C(=O)N1CCCC1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O4/c1-5(12)7(10)8(13)11-4-2-3-6(11)9(14)15/h5-7,12H,2-4,10H2,1H3,(H,14,15)

> <INCHI_KEY>
QOLYAJSZHIJCTO-UHFFFAOYSA-N

> <FORMULA>
C9H16N2O4

> <MOLECULAR_WEIGHT>
216.2343

> <EXACT_MASS>
216.11100701

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
21.49094617297994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2-amino-3-hydroxybutanoyl)pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.64

> <JCHEM_LOGP>
-3.7379822353191408

> <ALOGPS_LOGS>
-0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.705648566920292

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6113968623837645

> <JCHEM_PKA_STRONGEST_BASIC>
7.915007223758969

> <JCHEM_POLAR_SURFACE_AREA>
103.86

> <JCHEM_REFRACTIVITY>
51.446299999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2-amino-3-hydroxybutanoyl)pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-FEB-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-FEB-13         0                                  
HETATM    1  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.795   0.620   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.475  -0.886   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -4.260   1.096   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.404   0.066   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.580   2.603   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
L-Threoninyl-L-proline	HMDB
T-p Dipeptide	HMDB
THR-Pro	HMDB
Threonine proline dipeptide	HMDB
Threonine-proline dipeptide	HMDB
Threoninylproline	HMDB
TP Dipeptide	HMDB
1-(2-Amino-3-hydroxybutanoyl)pyrrolidine-2-carboxylate	Generator

Chemical Formula

C₉H₁₆N₂O₄

Average Molecular Weight

216.2343

Monoisotopic Molecular Weight

216.11100701

IUPAC Name

1-(2-amino-3-hydroxybutanoyl)pyrrolidine-2-carboxylic acid

Traditional Name

1-(2-amino-3-hydroxybutanoyl)pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(O)C(N)C(=O)N1CCCC1C(O)=O

InChI Identifier

InChI=1S/C9H16N2O4/c1-5(12)7(10)8(13)11-4-2-3-6(11)9(14)15/h5-7,12H,2-4,10H2,1H3,(H,14,15)

InChI Key

QOLYAJSZHIJCTO-UHFFFAOYSA-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
Proline or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Tertiary carboxylic acid amide
Pyrrolidine
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Amino acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Carboxylic acid
Alcohol
Organonitrogen compound
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.6	ALOGPS
logP	-3.7	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	7.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.45 m³·mol⁻¹	ChemAxon
Polarizability	21.49 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 Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Threoninyl-Proline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-493a0d5f933d4ebc2da8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Threoninyl-Proline GC-MS (2 TMS) - 70eV, Positive	splash10-00kf-9551000000-0c4e015667103e500186	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threoninyl-Proline 10V, Positive-QTOF	splash10-0002-0910000000-d9a09405e661742bbc72	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threoninyl-Proline 20V, Positive-QTOF	splash10-006t-4900000000-5229019dc4fbc062ae3d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threoninyl-Proline 40V, Positive-QTOF	splash10-0aor-9200000000-7081250ba94dd56110d7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threoninyl-Proline 10V, Negative-QTOF	splash10-01b9-1950000000-f3936b129dc309bc0886	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threoninyl-Proline 20V, Negative-QTOF	splash10-00di-3900000000-25cfa2f93950c17fcd16	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Threoninyl-Proline 40V, Negative-QTOF	splash10-00di-9400000000-c9b1e9e5eeb32a8f456b	2017-09-01	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14647614

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Meister I, Zhang P, Sinha A, Skold CM, Wheelock AM, Izumi T, Chaleckis R, Wheelock CE: High-Precision Automated Workflow for Urinary Untargeted Metabolomic Epidemiology. Anal Chem. 2021 Mar 30;93(12):5248-5258. doi: 10.1021/acs.analchem.1c00203. Epub 2021 Mar 19. [PubMed:33739820 ]

Showing metabocard for Threoninyl-Proline (HMDB0341432)

MOL for HMDB0341432 (Threoninyl-Proline)

3D MOL for HMDB0341432 (Threoninyl-Proline)

3D SDF for HMDB0341432 (Threoninyl-Proline)

3D-SDF for HMDB0341432 (Threoninyl-Proline)

PDB for HMDB0341432 (Threoninyl-Proline)

3D PDB for HMDB0341432 (Threoninyl-Proline)

SMILES for HMDB0341432 (Threoninyl-Proline)

INCHI for HMDB0341432 (Threoninyl-Proline)

Structure for HMDB0341432 (Threoninyl-Proline)

3D Structure for HMDB0341432 (Threoninyl-Proline)

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra