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Showing metabocard for pyroglutamylhistidine (HMDB0341380)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 20:48:27 UTC
Update Date2022-09-22 18:34:52 UTC
HMDB IDHMDB0341380
Secondary Accession NumbersNone
Metabolite Identification
Common Namepyroglutamylhistidine
Descriptionpyroglutamylhistidine, also known as pglu-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. Based on a literature review very few articles have been published on pyroglutamylhistidine.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for HMDB0341380 (pyroglutamylhistidine)


  Mrv1652309092223262D          

 19 20  0  0  0  0            999 V2000
    0.5923   -3.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -2.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1222   -2.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -2.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -2.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -3.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3538   -3.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -4.6286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337   -4.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -3.8440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -1.2966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -0.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7357   -1.2966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -0.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3538    0.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    1.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337    1.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    1.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887    0.4258    0.0000 N   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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 11  4  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
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3D MOL for HMDB0341380 (pyroglutamylhistidine)

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3D SDF for HMDB0341380 (pyroglutamylhistidine)

  Mrv1652309092223262D          

 19 20  0  0  0  0            999 V2000
    0.5923   -3.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -2.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1222   -2.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -2.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -2.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -3.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3538   -3.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -4.6286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337   -4.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887   -3.8440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -1.2966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -0.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7357   -1.2966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -0.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3538    0.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    1.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4337    1.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    1.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6887    0.4258    0.0000 N   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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 11  4  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341380

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C(CC1=CN=CN1)N=C(O)C1CCC(O)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N4O4/c16-9-2-1-7(14-9)10(17)15-8(11(18)19)3-6-4-12-5-13-6/h4-5,7-8H,1-3H2,(H,12,13)(H,14,16)(H,15,17)(H,18,19)

> <INCHI_KEY>
XFWCSGJOVUQCME-UHFFFAOYSA-N

> <FORMULA>
C11H14N4O4

> <MOLECULAR_WEIGHT>
266.257

> <EXACT_MASS>
266.101504947

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.053286728902595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[hydroxy(5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl)methylidene]amino}-3-(1H-imidazol-5-yl)propanoic acid

> <JCHEM_LOGP>
-1.6490921009695692

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.938410082337765

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2237601416717987

> <JCHEM_PKA_STRONGEST_BASIC>
6.781560663535208

> <JCHEM_POLAR_SURFACE_AREA>
131.16

> <JCHEM_REFRACTIVITY>
63.99030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-{[hydroxy(5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl)methylidene]amino}-3-(3H-imidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for HMDB0341380 (pyroglutamylhistidine)
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PDB for HMDB0341380 (pyroglutamylhistidine)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       1.106  -6.270   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.106  -4.730   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.228  -3.960   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.439  -3.960   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.773  -4.730   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.773  -6.270   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.527  -7.175   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.003  -8.640   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.543  -8.640   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.019  -7.175   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.439  -2.420   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.773  -1.650   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.107  -2.420   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.773  -0.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.527   0.795   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.003   2.260   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.543   2.260   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.448   3.505   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       5.019   0.795   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    4   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

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3D PDB for HMDB0341380 (pyroglutamylhistidine)
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SMILES for HMDB0341380 (pyroglutamylhistidine)
OC(=O)C(CC1=CN=CN1)N=C(O)C1CCC(O)=N1
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INCHI for HMDB0341380 (pyroglutamylhistidine)
InChI=1S/C11H14N4O4/c16-9-2-1-7(14-9)10(17)15-8(11(18)19)3-6-4-12-5-13-6/h4-5,7-8H,1-3H2,(H,12,13)(H,14,16)(H,15,17)(H,18,19)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
PGlu-hisMeSH
Chemical FormulaC11H14N4O4
Average Molecular Weight266.257
Monoisotopic Molecular Weight266.101504947
IUPAC Name2-{[hydroxy(5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl)methylidene]amino}-3-(1H-imidazol-5-yl)propanoic acid
Traditional Name2-{[hydroxy(5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl)methylidene]amino}-3-(3H-imidazol-4-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(CC1=CN=CN1)N=C(O)C1CCC(O)=N1
InChI Identifier
InChI=1S/C11H14N4O4/c16-9-2-1-7(14-9)10(17)15-8(11(18)19)3-6-4-12-5-13-6/h4-5,7-8H,1-3H2,(H,12,13)(H,14,16)(H,15,17)(H,18,19)
InChI KeyXFWCSGJOVUQCME-UHFFFAOYSA-N
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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentDipeptides  
Alternative Parents
Substituents
  • Alpha-dipeptide
    • 

  • Histidine or derivatives
    • 

  • N-acyl-alpha-amino acid
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • Proline or derivatives
    • 

  • Alpha-amino acid amide
    • 

  • Alpha-amino acid or derivatives
    • 

  • Imidazolyl carboxylic acid derivative
    • 

  • Pyrrolidine carboxylic acid or derivatives
    • 

  • Pyrrolidine-2-carboxamide
    • 

  • 2-pyrrolidone
    • 

  • Pyrrolidone
    • 

  • Pyrrolidine
    • 

  • Heteroaromatic compound
    • 

  • Azole
    • 

  • Imidazole
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-1.6ChemAxon
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area131.16 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.99 m³·mol⁻¹ChemAxon
Polarizability25.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Predicted Kovats Retention Indices
Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3064814  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3839181  
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920  ]