NP-MRD: Showing NP-Card for Phenylalanylhistidine (NP0136596)

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Record Information

Version

2.0

Created at

2022-05-12 15:18:38 UTC

Updated at

2022-05-12 15:18:38 UTC

NP-MRD ID

NP0136596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenylalanylhistidine

Description

Phe-His, also known as F-H or L-phe-L-his, 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. Phe-His is possibly neutral. A dipeptide composed of L-phenylalanine and L-histidine joined by a peptide linkage.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -2.0231    2.2448   -0.4193 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    0.9868    0.0136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2752   -0.1298   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6703   -0.0393   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1212   -0.6714    1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4317   -0.5744    1.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3500    0.1450    0.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9329    0.7885   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6265    0.6879   -0.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448    0.9437   -0.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503    1.9261   -0.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187   -0.1528   -0.0969 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2280   -0.1013   -0.5241 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1372   -0.3778    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5720   -0.2966    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2851    0.1935   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6075   -0.0020   -0.4720 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7135   -0.5988    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4953   -0.7893    1.2391 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3164   -1.2139   -1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -1.8983   -1.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247   -1.4747   -2.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6732    2.4521   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8813    2.9995    0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5054    0.8684    1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908   -0.0378   -1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8705   -1.1322   -0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4540   -1.2592    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8021   -1.0716    2.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3881    0.2553    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6399    1.3688   -1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3281    1.1986   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4494   -0.9919    0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121    0.8345   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9178    0.2599    1.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354   -1.4453    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178    0.6684   -1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6338   -0.9034    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2691   -1.2374    2.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7787   -2.4226   -2.3137 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
  8  9  2  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 13 20  1  0
 20 22  1  0
 20 21  2  0
  9  4  1  0
 19 15  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  1
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  6
 14 35  1  0
 14 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
M  END


  Mrv1652304062014052D          

 22 23  0  0  0  0            999 V2000
 9998.183210000.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8974 9999.7786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.611510000.1916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.3261 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.039910000.1916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.7537 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.039910001.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.3261 9998.9540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8974 9998.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6115 9998.5427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1832 9998.5427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.797410000.2729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1300 9999.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3849 9999.0033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2099 9999.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4648 9999.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.897810001.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.183410001.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.468810001.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.468810000.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1832 9999.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.897810000.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 15 16  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
  6 20  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  1 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18N4O3/c16-12(6-10-4-2-1-3-5-10)14(20)19-13(15(21)22)7-11-8-17-9-18-11/h1-5,8-9,12-13H,6-7,16H2,(H,17,18)(H,19,20)(H,21,22)/t12-,13-/m0/s1

> <INCHI_KEY>
OHUXOEXBXPZKPT-STQMWFEESA-N

> <FORMULA>
C15H18N4O3

> <MOLECULAR_WEIGHT>
302.334

> <EXACT_MASS>
302.137890456

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.858082203642724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-2.2983543042325083

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.771283088507897

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4679068877380868

> <JCHEM_PKA_STRONGEST_BASIC>
8.032936894967133

> <JCHEM_POLAR_SURFACE_AREA>
121.09999999999998

> <JCHEM_REFRACTIVITY>
79.97540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-(3H-imidazol-4-yl)propanoic 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    8663.2758667.024   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.6088666.253   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8665.9418667.024   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8667.2758666.253   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.6088667.024   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.9408666.253   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8668.6088668.565   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8667.2758664.714   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8664.6088664.714   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8665.9418663.946   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8663.2758663.946   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    8660.6888667.176   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8659.4438666.271   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8659.9188664.806   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8661.4588664.806   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.9348666.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8673.9438668.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8672.6098669.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8671.2758668.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.2758667.024   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.6098666.254   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.9438667.024   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   20                                                       
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   16                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   16   14                                                       
CONECT   16   15   12    1                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21    6                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
F-H	ChEBI
FH	ChEBI
L-Phe-L-his	ChEBI
Phenylalanylhistidine	MeSH
His-phe	MeSH
Histidylphenylalanine	MeSH
F-H dipeptide	HMDB
FH dipeptide	HMDB
L-Phenylalanyl-L-histidine	HMDB
N-L-Phenylalanyl-L-histidine	HMDB
N-Phenylalanylhistidine	HMDB
Phe-His	HMDB
Phenylalanine histidine dipeptide	HMDB
Phenylalanine-histidine dipeptide	HMDB
Phenylalanyl-histidine	HMDB

Chemical Formula

C₁₅H₁₈N₄O₃

Average Mass

302.3340 Da

Monoisotopic Mass

302.13789 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-phenylpropanamido]-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C15H18N4O3/c16-12(6-10-4-2-1-3-5-10)14(20)19-13(15(21)22)7-11-8-17-9-18-11/h1-5,8-9,12-13H,6-7,16H2,(H,17,18)(H,19,20)(H,21,22)/t12-,13-/m0/s1

InChI Key

OHUXOEXBXPZKPT-STQMWFEESA-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
Histidine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
Imidazolyl carboxylic acid derivative
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Fatty amide
Fatty acyl
Heteroaromatic compound
Azole
Imidazole
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid
Primary aliphatic amine
Hydrocarbon derivative
Amine
Carbonyl group
Organic oxygen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Primary amine
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73634 )

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	-1.6	ALOGPS
logP	-2.3	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	8.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.1 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	79.98 m³·mol⁻¹	ChemAxon
Polarizability	30.86 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

HMDB0028997

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8141751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9966159

PDB ID

Not Available

ChEBI ID

73634

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phenylalanylhistidine (NP0136596)

MOL for NP0136596 (Phenylalanylhistidine)

3D MOL for NP0136596 (Phenylalanylhistidine)

3D SDF for NP0136596 (Phenylalanylhistidine)

3D-SDF for NP0136596 (Phenylalanylhistidine)

PDB for NP0136596 (Phenylalanylhistidine)

3D PDB for NP0136596 (Phenylalanylhistidine)

SMILES for NP0136596 (Phenylalanylhistidine)

INCHI for NP0136596 (Phenylalanylhistidine)

Structure for NP0136596 (Phenylalanylhistidine)

3D Structure for NP0136596 (Phenylalanylhistidine)