NP-MRD: Showing NP-Card for Histidylhydroxyproline (NP0136495)

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Record Information

Version

1.0

Created at

2022-05-12 15:16:00 UTC

Updated at

2022-05-12 15:16:00 UTC

NP-MRD ID

NP0136495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidylhydroxyproline

Description

Histidinylhydroxyproline, also known as his-hyp, 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. Histidinylhydroxyproline is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    1.1412   -0.8943   -0.1033 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0425    0.3233    0.5650 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0662    1.2682   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257    0.7092    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0314   -0.1319   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2748   -0.4294   -0.4029 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4466    0.2122    0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3013    0.9113    1.0224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2789    0.9077    0.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480    2.0705    1.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4323    0.2057    0.0822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -1.1190   -0.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9342   -1.5348   -0.3419 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2200   -2.4686   -1.3082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -0.2063   -0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454    0.8072    0.0318 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2054    1.2449    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975    1.0832    2.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4444    1.8392    1.4828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1830   -0.9002   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5343   -1.7020    0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145    0.1722    1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    2.2478    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7789    1.4304   -1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6675   -0.5338   -1.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0045   -1.0346   -0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3080    0.2119    1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764   -1.1175   -1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954   -1.8650    0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446   -1.9326    0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0724   -3.3729   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -0.0881   -1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6413   -0.1970   -0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    1.7008   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9555    2.1823    0.6778 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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
  8  4  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  1
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  6
 19 35  1  0
M  END


  Mrv1652304062013482D          

 19 20  0  0  0  0            999 V2000
10002.1009 9999.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8128 9999.2054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.100910000.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8095 9997.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7175 9999.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.0502 9999.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3051 9998.4306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1301 9998.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3850 9999.2152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.717510000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.432010000.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.574110000.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.288610000.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110001.7627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.003110000.9377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.487810001.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.680910001.9297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.268410001.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.820410000.6022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7  4  1  1  0  0  0
  9  1  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  6  0  0  0
 10 15  1  0  0  0  0
 13 12  1  0  0  0  0
 12 16  2  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CNC=N1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N4O4/c12-8(1-6-3-13-5-14-6)10(17)15-4-7(16)2-9(15)11(18)19/h3,5,7-9,16H,1-2,4,12H2,(H,13,14)(H,18,19)/t7-,8+,9+/m1/s1

> <INCHI_KEY>
WEUKYXZXBBLBOY-VGMNWLOBSA-N

> <FORMULA>
C11H16N4O4

> <MOLECULAR_WEIGHT>
268.273

> <EXACT_MASS>
268.117155011

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.644993063629375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.88

> <JCHEM_LOGP>
-4.628090380154898

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.084175698451858

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.296491209212351

> <JCHEM_PKA_STRONGEST_BASIC>
7.831668205960374

> <JCHEM_POLAR_SURFACE_AREA>
132.54000000000002

> <JCHEM_REFRACTIVITY>
63.7977

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-1-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]-4-hydroxypyrrolidine-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    8670.5888665.953   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8671.9178665.183   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.5888667.490   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.3118662.504   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0    8668.0068666.107   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8666.7608665.202   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.2368663.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.7768663.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.2528665.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0068667.647   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8669.3408668.417   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8664.0058668.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3398667.647   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8666.6728669.957   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8666.6728668.417   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.8448669.948   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8662.3388670.269   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    8661.5688668.935   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8662.5988667.791   0.000  0.00  0.00           N+0
CONECT    1    2    3    9                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    7                                                            
CONECT    5    6    9   10                                                  
CONECT    6    7    5                                                       
CONECT    7    6    8    4                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5    1                                                  
CONECT   10    5   11   15                                                  
CONECT   11   10                                                            
CONECT   12   13   16   19                                                  
CONECT   13   15   12                                                       
CONECT   14   15                                                            
CONECT   15   13   14   10                                                  
CONECT   16   12   17                                                       
CONECT   17   16   18                                                       
CONECT   18   19   17                                                       
CONECT   19   18   12                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
His-hyp	HMDB
Histidine hydroxyproline dipeptide	HMDB
Histidine-hydroxyproline dipeptide	HMDB
Histidinyl-hydroxyproline	HMDB
L-His-L-hyp	HMDB
L-Histidinyl-L-hydroxyproline	HMDB
Histidinylhydroxyproline	HMDB
(2S,4R)-1-[(2S)-2-Amino-3-(1H-imidazol-5-yl)propanoyl]-4-hydroxypyrrolidine-2-carboxylate	Generator
Histidyl-hydroxyproline	HMDB
Histidylhydroxyproline	HMDB
L-Histidyl-L-hydroxyproline	HMDB
N-Histidinylhydroxyproline	HMDB
N-Histidylhydroxyproline	HMDB
N-L-Histidinyl-L-hydroxyproline	HMDB
N-L-Histidyl-L-hydroxyproline	HMDB

Chemical Formula

C₁₁H₁₆N₄O₄

Average Mass

268.2730 Da

Monoisotopic Mass

268.11716 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

N[C@@H](CC1=CNC=N1)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI Identifier

InChI=1S/C11H16N4O4/c12-8(1-6-3-13-5-14-6)10(17)15-4-7(16)2-9(15)11(18)19/h3,5,7-9,16H,1-2,4,12H2,(H,13,14)(H,18,19)/t7-,8+,9+/m1/s1

InChI Key

WEUKYXZXBBLBOY-VGMNWLOBSA-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 or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Aralkylamine
Fatty acyl
Fatty amide
Azole
Imidazole
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organooxygen compound
Organonitrogen 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	-2.9	ALOGPS
logP	-4.6	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.54 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	63.8 m³·mol⁻¹	ChemAxon
Polarizability	25.64 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

HMDB0028886

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8075714

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9900059

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Histidylhydroxyproline (NP0136495)

MOL for NP0136495 (Histidylhydroxyproline)

3D MOL for NP0136495 (Histidylhydroxyproline)

3D SDF for NP0136495 (Histidylhydroxyproline)

3D-SDF for NP0136495 (Histidylhydroxyproline)

PDB for NP0136495 (Histidylhydroxyproline)

3D PDB for NP0136495 (Histidylhydroxyproline)

SMILES for NP0136495 (Histidylhydroxyproline)

INCHI for NP0136495 (Histidylhydroxyproline)

Structure for NP0136495 (Histidylhydroxyproline)

3D Structure for NP0136495 (Histidylhydroxyproline)