NP-MRD: Showing NP-Card for Histidylproline (NP0136502)

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Record Information

Version

1.0

Created at

2022-05-12 15:16:11 UTC

Updated at

2022-05-12 15:16:11 UTC

NP-MRD ID

NP0136502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidylproline

Description

His-Pro, also known as histidylproline or HP, 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. His-Pro is a very strong basic compound (based on its pKa). A dipeptide formed from L-histidine and L-proline residues.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    1.7591   -1.9662   -1.1744 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337   -1.0126   -0.4113 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5066    0.3987   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8922    0.4403   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307    0.7628    1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777    0.6794    1.1192 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0473    0.3154   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792    0.1630   -0.9067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594   -0.9653   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331   -1.5745   -2.0345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181   -0.3256   -0.2544 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4746    0.3558    0.9948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650   -0.3252    1.6931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759   -0.3185    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718   -0.2147   -0.7122 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1409    1.0829   -1.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3074    1.2711   -1.8221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2039    2.0673   -1.5531 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -2.4171   -1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0737   -2.7605   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0587   -1.2419    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    0.5824   -1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8354    1.0884   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6602    1.0331    1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2569    0.8790    1.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0863    0.1626   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    1.4434    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    0.2240    1.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -1.3551    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9929    0.2565    2.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2573   -1.2720    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3489    0.5435    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1302   -1.0364   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3455    3.0363   -1.2981 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  1  0
  7  8  2  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
  8  4  1  0
 15 11  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  6
 18 34  1  0
M  END


  Mrv1652304062013492D          

 18 19  0  0  0  0            999 V2000
 9998.880610000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5954 9999.7892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.309310000.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.309310001.0261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5954 9998.9638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.494910000.2836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8275 9999.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0824 9999.0140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9074 9999.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1623 9999.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.692210000.2742    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0248 9999.7892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.2797 9999.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1047 9999.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3596 9999.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.692210001.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.977810001.5117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.406710001.5117    0.0000 O   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  5  1  1  0  0  0
  3  4  2  0  0  0  0
  1 10  1  0  0  0  0
  9 10  2  0  0  0  0
  8  9  1  0  0  0  0
  7  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6  7  2  0  0  0  0
 14 15  1  0  0  0  0
  3 12  1  0  0  0  0
 13 14  1  0  0  0  0
 12 13  1  0  0  0  0
 11 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CNC=N1)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N4O3/c12-8(4-7-5-13-6-14-7)10(16)15-3-1-2-9(15)11(17)18/h5-6,8-9H,1-4,12H2,(H,13,14)(H,17,18)/t8-,9-/m0/s1

> <INCHI_KEY>
LNCFUHAPNTYMJB-IUCAKERBSA-N

> <FORMULA>
C11H16N4O3

> <MOLECULAR_WEIGHT>
252.274

> <EXACT_MASS>
252.122240391

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.421525070669322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.61

> <JCHEM_LOGP>
-3.479930618344341

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.092109900434867

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.410097666917717

> <JCHEM_PKA_STRONGEST_BASIC>
7.8317192191108385

> <JCHEM_POLAR_SURFACE_AREA>
112.31000000000002

> <JCHEM_REFRACTIVITY>
62.47980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxylic 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    8664.5778667.042   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.9118666.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.2448667.042   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8667.2448668.582   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    8665.9118664.732   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0    8661.9908667.196   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8660.7458666.291   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8661.2208664.826   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    8662.7608664.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.2368666.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8669.8258667.179   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8668.5808666.273   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8669.0558664.809   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.5958664.809   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.0718666.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.8258668.719   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8668.4928669.489   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8671.1598669.489   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    5                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6   10    7                                                       
CONECT    7    8    6                                                       
CONECT    8    9    7                                                       
CONECT    9   10    8                                                       
CONECT   10    1    9    6                                                  
CONECT   11   15   12   16                                                  
CONECT   12    3   13   11                                                  
CONECT   13   14   12                                                       
CONECT   14   15   13                                                       
CONECT   15   14   11                                                       
CONECT   16   11   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Histidinyl-proline	ChEBI
Histidylproline	ChEBI
HP	ChEBI
L-His-L-pro	ChEBI
H-P dipeptide	HMDB
HP dipeptide	HMDB
His-Pro	HMDB
Histidine proline dipeptide	HMDB
Histidine-proline dipeptide	HMDB
Histidinylproline	HMDB
Histidyl-proline	HMDB
L-Histidinyl-L-proline	HMDB
L-Histidyl-L-proline	HMDB
N-Histidinylproline	HMDB
N-Histidylproline	HMDB
N-L-Histidinyl-L-proline	HMDB
N-L-Histidyl-L-proline	HMDB

Chemical Formula

C₁₁H₁₆N₄O₃

Average Mass

252.2740 Da

Monoisotopic Mass

252.12224 Da

IUPAC Name

(2S)-1-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CC1=CNC=N1)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C11H16N4O3/c12-8(4-7-5-13-6-14-7)10(16)15-3-1-2-9(15)11(17)18/h5-6,8-9H,1-4,12H2,(H,13,14)(H,17,18)/t8-,9-/m0/s1

InChI Key

LNCFUHAPNTYMJB-IUCAKERBSA-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
Histidine or derivatives
N-acyl-alpha-amino acid
Proline or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Aralkylamine
Azole
Imidazole
Heteroaromatic compound
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:74055 )

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	-2.6	ALOGPS
logP	-3.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.48 m³·mol⁻¹	ChemAxon
Polarizability	24.42 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

HMDB0028893

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

134260

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152322

PDB ID

Not Available

ChEBI ID

74055

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Histidylproline (NP0136502)

MOL for NP0136502 (Histidylproline)

3D MOL for NP0136502 (Histidylproline)

3D SDF for NP0136502 (Histidylproline)

3D-SDF for NP0136502 (Histidylproline)

PDB for NP0136502 (Histidylproline)

3D PDB for NP0136502 (Histidylproline)

SMILES for NP0136502 (Histidylproline)

INCHI for NP0136502 (Histidylproline)

Structure for NP0136502 (Histidylproline)

3D Structure for NP0136502 (Histidylproline)