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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:47:36 UTC

Update Date

2022-09-22 18:34:52 UTC

HMDB ID

HMDB0341378

Secondary Accession Numbers

None

Metabolite Identification

Common Name

pyroglutamylalanine

Description

pyroglutamylalanine 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 pyroglutamylalanine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092223252D          

 14 14  0  0  0  0            999 V2000
    0.5678    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    4.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  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
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  6 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341378

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(N=C(O)C1CCC(O)=N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O4/c1-4(8(13)14)9-7(12)5-2-3-6(11)10-5/h4-5H,2-3H2,1H3,(H,9,12)(H,10,11)(H,13,14)

> <INCHI_KEY>
YIJVJUARZXCJJP-UHFFFAOYSA-N

> <FORMULA>
C8H12N2O4

> <MOLECULAR_WEIGHT>
200.194

> <EXACT_MASS>
200.079706874

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.86434830752185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.022746414121611373

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.292574523865318

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3935268984466487

> <JCHEM_PKA_STRONGEST_BASIC>
1.8177272286230255

> <JCHEM_POLAR_SURFACE_AREA>
102.48000000000002

> <JCHEM_REFRACTIVITY>
46.4286

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0       1.060   6.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.393   4.390   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.727   6.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.727   8.240   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.061   5.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6                                                       
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₈H₁₂N₂O₄

Average Molecular Weight

200.194

Monoisotopic Molecular Weight

200.079706874

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(N=C(O)C1CCC(O)=N1)C(O)=O

InChI Identifier

InChI=1S/C8H12N2O4/c1-4(8(13)14)9-7(12)5-2-3-6(11)10-5/h4-5H,2-3H2,1H3,(H,9,12)(H,10,11)(H,13,14)

InChI Key

YIJVJUARZXCJJP-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.

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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Proline or derivatives
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Pyrrolidone
2-pyrrolidone
Pyrrolidine
Lactam
Carboxamide group
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.023	ChemAxon
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	1.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.48 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.43 m³·mol⁻¹	ChemAxon
Polarizability	18.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4176342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4996385

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for pyroglutamylalanine (HMDB0341378)

MOL for HMDB0341378 (pyroglutamylalanine)

3D MOL for HMDB0341378 (pyroglutamylalanine)

3D SDF for HMDB0341378 (pyroglutamylalanine)

3D-SDF for HMDB0341378 (pyroglutamylalanine)

PDB for HMDB0341378 (pyroglutamylalanine)

3D PDB for HMDB0341378 (pyroglutamylalanine)

SMILES for HMDB0341378 (pyroglutamylalanine)

INCHI for HMDB0341378 (pyroglutamylalanine)

Structure for HMDB0341378 (pyroglutamylalanine)

3D Structure for HMDB0341378 (pyroglutamylalanine)

Predicted Kovats Retention Indices