NP-MRD: Showing NP-Card for Threonylphenylalanine (NP0136653)

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Record Information

Version

2.0

Created at

2022-05-12 15:20:04 UTC

Updated at

2022-05-12 15:20:04 UTC

NP-MRD ID

NP0136653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Threonylphenylalanine

Description

(2S)-2-{[(2S,3R)-2-amino-1,3-dihydroxybutylidene]amino}-3-phenylpropanoic acid 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 (2S)-2-{[(2S,3R)-2-amino-1,3-dihydroxybutylidene]amino}-3-phenylpropanoic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
    4.0659    1.3919   -1.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329   -0.0683   -1.2832 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3344   -0.5653   -1.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3230   -0.4637   -0.0189 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2995   -1.9113    0.0357 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813    0.0794    0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7873    1.3202    0.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661   -0.7719    0.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830   -0.2199    0.4367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3667   -0.6672   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -0.1138   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783   -0.7626    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0270   -0.2170    0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2886    1.0450   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    1.7181   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178    1.1560   -1.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -0.5605    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3955   -1.3127    2.5466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2764   -0.1397    2.2332 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0705    1.6730   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3619    1.6875   -2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8954    2.0156   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5335   -0.5625   -2.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8960    0.0054   -0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0090   -0.1567    0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6983   -2.3067   -0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9115   -2.2035    0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0199   -1.8073    0.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3736    0.8858    0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -1.7895   -0.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533   -0.4318   -1.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6200   -1.7587    0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8602   -0.7242    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2564    1.5225   -0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201    2.7069   -1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2153    1.6917   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    0.6156    2.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 19  1  0
 17 18  2  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  4 25  1  1
  5 26  1  0
  5 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
M  END


  Mrv1652304062014152D          

 19 19  0  0  0  0            999 V2000
10009.133410009.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.848810009.7161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10010.561510009.3052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.274310009.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.987010009.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.274310010.5390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.421610009.7161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10007.707910009.3052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10006.996210009.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.707910008.4821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.421610010.5390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10009.133410008.4821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.561510008.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.276110008.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.276110007.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.990610006.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.705110007.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.705110008.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.990610008.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  3 13  1  6  0  0  0
 13 14  1  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
 18 19  2  0  0  0  0
 14 15  2  0  0  0  0
 19 14  1  0  0  0  0
  8 10  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0136653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O4/c1-8(16)11(14)12(17)15-10(13(18)19)7-9-5-3-2-4-6-9/h2-6,8,10-11,16H,7,14H2,1H3,(H,15,17)(H,18,19)/t8-,10+,11+/m1/s1

> <INCHI_KEY>
IQHUITKNHOKGFC-MIMYLULJSA-N

> <FORMULA>
C13H18N2O4

> <MOLECULAR_WEIGHT>
266.297

> <EXACT_MASS>
266.126657068

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.4976114934365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
-1.41

> <JCHEM_LOGP>
-2.3537216256598192

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.404978119870478

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7065859877666574

> <JCHEM_PKA_STRONGEST_BASIC>
7.922169725642668

> <JCHEM_POLAR_SURFACE_AREA>
112.65

> <JCHEM_REFRACTIVITY>
68.37620000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-phenylpropanoic acid

> <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  C   UNK     0    8683.7168684.036   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8685.0518684.803   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8686.3818684.036   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8687.7128684.803   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8689.0428684.036   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8687.7128686.339   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8682.3878684.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8681.0558684.036   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8679.7268684.803   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8681.0558682.500   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8682.3878686.339   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    8683.7168682.500   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8686.3818682.500   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8687.7158681.730   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8687.7158680.190   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8689.0498679.420   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8690.3838680.190   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8690.3838681.730   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8689.0498682.500   0.000  0.00  0.00           C+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    1                                                            
CONECT   13    3   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   16   14                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(2S,3R)-2-amino-1,3-dihydroxybutylidene]amino}-3-phenylpropanoate	Generator
L-Thr-L-Phe	HMDB
L-Threoninyl-L-phenylalanine	HMDB
L-Threonyl-L-phenylalanine	HMDB
N-L-Threoninyl-L-phenylalanine	HMDB
N-L-Threonyl-L-phenylalanine	HMDB
N-Threoninylphenylalanine	HMDB
N-Threonylphenylalanine	HMDB
T-F dipeptide	HMDB
TF dipeptide	HMDB
Thr-Phe	HMDB
Threonine phenylalanine dipeptide	HMDB
Threonine-phenylalanine dipeptide	HMDB
Threoninyl-phenylalanine	HMDB
Threoninylphenylalanine	HMDB
Threonyl-phenylalanine	HMDB
Threonylphenylalanine	HMDB

Chemical Formula

C₁₃H₁₈N₂O₄

Average Mass

266.2970 Da

Monoisotopic Mass

266.12666 Da

IUPAC Name

(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-phenylpropanoic acid

Traditional Name

(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](N)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C13H18N2O4/c1-8(16)11(14)12(17)15-10(13(18)19)7-9-5-3-2-4-6-9/h2-6,8,10-11,16H,7,14H2,1H3,(H,15,17)(H,18,19)/t8-,10+,11+/m1/s1

InChI Key

IQHUITKNHOKGFC-MIMYLULJSA-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
Phenylalanine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Monocyclic benzene moiety
Fatty amide
N-acyl-amine
Fatty acyl
Benzenoid
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Amine
Organic salt
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Organic zwitterion
Organonitrogen compound
Organooxygen compound
Alcohol
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:74862 )

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	-1.4	ALOGPS
logP	-2.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	7.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.65 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	68.38 m³·mol⁻¹	ChemAxon
Polarizability	26.5 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

External Links

HMDB ID

HMDB0029068

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5374146

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7010579

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Threonylphenylalanine (NP0136653)

MOL for NP0136653 (Threonylphenylalanine)

3D MOL for NP0136653 (Threonylphenylalanine)

3D SDF for NP0136653 (Threonylphenylalanine)

3D-SDF for NP0136653 (Threonylphenylalanine)

PDB for NP0136653 (Threonylphenylalanine)

3D PDB for NP0136653 (Threonylphenylalanine)

SMILES for NP0136653 (Threonylphenylalanine)

INCHI for NP0136653 (Threonylphenylalanine)

Structure for NP0136653 (Threonylphenylalanine)

3D Structure for NP0136653 (Threonylphenylalanine)