NP-MRD: Showing NP-Card for Tyrosyl-Proline (NP0136695)

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Record Information

Version

2.0

Created at

2022-05-12 15:21:08 UTC

Updated at

2022-05-12 15:21:08 UTC

NP-MRD ID

NP0136695

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tyrosyl-Proline

Description

Tyrosyl-Proline, also known as y-p dipeptide or tyr-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. Tyrosyl-Proline is a very strong basic compound (based on its pKa). Tyrosyl-Proline is a dipeptide composed of tyrosine and proline. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. 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.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.1140   -0.3965    0.7614 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.4767   -0.2907 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3628   -0.1074   -1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5777   -0.4584   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874   -1.7055    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9404   -1.9927    0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8902   -1.0098    0.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0449   -1.3117    1.7141 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7058    0.2541    0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535    0.5043   -0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8432    0.8784   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5924    1.6282   -2.1364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1862    0.5104   -0.9022 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2899    0.9343   -1.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4395    0.9214   -0.7454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1998   -0.4495   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6965   -0.3156    0.1724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6854    0.4303    1.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930   -0.1939    2.4889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666    1.7220    1.6243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572   -0.0917    1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1059   -1.3890    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513    1.3851    0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0173   -1.0070   -1.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650    0.6313   -1.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -2.4980   -0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -2.9942    1.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7442   -0.5930    1.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4771    1.0011    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4074    1.4780   -0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096    0.1693   -2.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1257    1.9467   -2.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906    1.6998   -0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4101    1.0256   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3492   -1.2283   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7845   -0.6183    0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2300   -1.3013    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    2.0649    2.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 18 19  2  0
 10  4  1  0
 17 13  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  1
 20 38  1  0
M  END


  Mrv1652304062014232D          

 20 21  0  0  0  0            999 V2000
    3.4656   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -2.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -3.0215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032   -2.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3748   -1.9596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8163   -3.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6448   -4.1256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6010   -3.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2140   -3.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987   -3.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6118   -3.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4402   -4.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0533   -5.2718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6556   -4.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0425   -4.4227    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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136695

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CC=C(O)C=C1)C(=O)N1CCCC1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O4/c15-11(8-9-3-5-10(17)6-4-9)13(18)16-7-1-2-12(16)14(19)20/h3-6,11-12,17H,1-2,7-8,15H2,(H,19,20)

> <INCHI_KEY>
VNYDHJARLHNEGA-UHFFFAOYSA-N

> <FORMULA>
C14H18N2O4

> <MOLECULAR_WEIGHT>
278.3037

> <EXACT_MASS>
278.126657074

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.905684996124457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-1.7549738068087664

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.518401087076585

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5536172213782637

> <JCHEM_PKA_STRONGEST_BASIC>
8.013763350791155

> <JCHEM_POLAR_SURFACE_AREA>
103.86

> <JCHEM_REFRACTIVITY>
72.08370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tyr-pro

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0       6.469  -2.425   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.136  -3.195   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.802  -2.425   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.136  -4.735   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.890  -5.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.366  -7.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.906  -7.105   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.381  -5.640   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.846  -5.164   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.166  -3.658   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.990  -6.195   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       8.670  -7.701   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      10.455  -5.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.599  -6.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.064  -6.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.209  -7.304   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.888  -8.810   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.033  -9.841   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.424  -9.286   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.279  -8.256   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                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
L-Tyrosyl-L-proline	HMDB
Tyr-pro	HMDB
Tyrosine proline dipeptide	HMDB
Tyrosine-proline dipeptide	HMDB
Tyrosylproline	HMDB
Y-p dipeptide	HMDB
YP dipeptide	HMDB
1-[2-Amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxylate	Generator
Tyrosyl-proline	MeSH

Chemical Formula

C₁₄H₁₈N₂O₄

Average Mass

278.3037 Da

Monoisotopic Mass

278.12666 Da

IUPAC Name

1-[2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

tyr-pro

CAS Registry Number

Not Available

SMILES

NC(CC1=CC=C(O)C=C1)C(=O)N1CCCC1C(O)=O

InChI Identifier

InChI=1S/C14H18N2O4/c15-11(8-9-3-5-10(17)6-4-9)13(18)16-7-1-2-12(16)14(19)20/h3-6,11-12,17H,1-2,7-8,15H2,(H,19,20)

InChI Key

VNYDHJARLHNEGA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Proline or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
Pyrrolidine carboxylic acid
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

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	-1.7	ALOGPS
logP	-1.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	8.01	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	4	ChemAxon
Refractivity	72.08 m³·mol⁻¹	ChemAxon
Polarizability	27.91 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029113

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

13055260

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Tyrosyl-Proline (NP0136695)

MOL for NP0136695 (Tyrosyl-Proline)

3D MOL for NP0136695 (Tyrosyl-Proline)

3D SDF for NP0136695 (Tyrosyl-Proline)

3D-SDF for NP0136695 (Tyrosyl-Proline)

PDB for NP0136695 (Tyrosyl-Proline)

3D PDB for NP0136695 (Tyrosyl-Proline)

SMILES for NP0136695 (Tyrosyl-Proline)

INCHI for NP0136695 (Tyrosyl-Proline)

Structure for NP0136695 (Tyrosyl-Proline)

3D Structure for NP0136695 (Tyrosyl-Proline)