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Showing NP-Card for Pyrroline hydroxycarboxylic acid (NP0086765)

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Record Information
Version2.0
Created at2022-05-11 16:30:22 UTC
Updated at2022-05-11 16:30:22 UTC
NP-MRD IDNP0086765
Secondary Accession NumbersNone
Natural Product Identification
Common NamePyrroline hydroxycarboxylic acid
DescriptionPyrroline hydroxycarboxylic acid, also known as L-1-pyrroline 3-hydroxy-5-carboxylate or 3-hydroxy-L-1-pyrroline-5-carboxylate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. The oxidation of pyrroline-carboxylate generates glutamate and pyrroline-hydroxycarboxylate, a reaction catalyzed by hydroxyproline oxidase (PMID: 500817 ). Pyrroline hydroxycarboxylic acid is a moderately basic compound (based on its pKa). Pyrroline hydroxycarboxylic acid exists in all living species, ranging from bacteria to humans. Within humans, pyrroline hydroxycarboxylic acid participates in a number of enzymatic reactions. In particular, pyrroline hydroxycarboxylic acid can be biosynthesized from 4-hydroxyproline; which is catalyzed by the enzyme proline dehydrogenase 1, mitochondrial. In addition, pyrroline hydroxycarboxylic acid can be biosynthesized from 4-hydroxyproline through the action of the enzyme pyrroline-5-carboxylate reductase 2. In humans, pyrroline hydroxycarboxylic acid is involved in the metabolic disorder called hyperornithinemia with gyrate atrophy (hoga). Pyrroline hydroxycarboxylic acid is found in Arabidopsis thaliana. Pyrroline hydroxycarboxylic acid is a metabolite identified in the urine of patients with type II hyperprolinemia.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086765 (Pyrroline hydroxycarboxylic acid)


  Mrv0541 02231219052D          

  9  9  0  0  0  0            999 V2000
   -0.2994    0.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2994   -0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4093    0.5268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157    0.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1219   -0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1219    0.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157    1.3454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283    0.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -1.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for NP0086765 (Pyrroline hydroxycarboxylic acid)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.7018    1.2110   -0.9026 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    0.3865   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7509   -0.0999    0.9356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -0.1199   -0.4628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3361    0.9052   -0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477   -0.0384   -0.3136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6628    0.5906    0.1547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -1.0404    0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987   -1.0643    0.5230 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4477   -0.8437    0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032   -0.6318   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067    1.5729   -1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988    1.4248    0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784   -0.4929   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2642   -0.1086    0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5637   -1.6513    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  9  1  0
  9  8  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  8  6  1  0
  7 15  1  0
  6 14  1  6
  5 12  1  0
  5 13  1  0
  4 11  1  6
  8 16  1  0
  3 10  1  0
M  END
Download

3D SDF for NP0086765 (Pyrroline hydroxycarboxylic acid)


  Mrv0541 02231219052D          

  9  9  0  0  0  0            999 V2000
   -0.2994    0.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2994   -0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4093    0.5268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157    0.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1219   -0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1219    0.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157    1.3454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283    0.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -1.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC(N=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)

> <INCHI_KEY>
WFOFKRKDDKGRIK-UHFFFAOYSA-N

> <FORMULA>
C5H7NO3

> <MOLECULAR_WEIGHT>
129.114

> <EXACT_MASS>
129.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
11.595062277388251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-1.4545071951925133

> <ALOGPS_LOGS>
-0.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.25483703022578

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7212230695209163

> <JCHEM_PKA_STRONGEST_BASIC>
2.5899435587205386

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
28.8459

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrroline-hydroxy-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086765 (Pyrroline hydroxycarboxylic acid)

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PDB for NP0086765 (Pyrroline hydroxycarboxylic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.559   0.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.559  -1.330   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.764   0.983   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.896   0.969   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.094  -1.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.094   0.205   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.896   2.511   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.226   0.191   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.184  -2.420   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9    6                                                  
CONECT    6    3    5                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0086765 (Pyrroline hydroxycarboxylic acid)
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SMILES for NP0086765 (Pyrroline hydroxycarboxylic acid)
OC1CC(N=C1)C(O)=O
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INCHI for NP0086765 (Pyrroline hydroxycarboxylic acid)
InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)
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View in JSmol
Synonyms
ValueSource
Pyrroline hydroxycarboxylateGenerator
3-Hydroxy-L-1-pyrroline-5-carboxylateHMDB
L-1-Pyrroline 3-hydroxy-5-carboxylateHMDB
L-1-Pyrroline-3-hydroxy-5-carboxylateHMDB
L-Delta1-Pyrroline 3-hydroxy-5-carboxylateHMDB
Pyrroline-hydroxy-carboxylateHMDB
3,4-Dihydro-3-hydroxy-2H-pyrrole-5-carboxylic acidHMDB
3-Hydroxy delta 1-pyrroline-5-carboxylic acidHMDB
3-Hydroxy delta 1-pyrroline-5-carboxylic acid, anionHMDB
Chemical FormulaC5H7NO3
Average Mass129.1140 Da
Monoisotopic Mass129.04259 Da
IUPAC Name4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid
Traditional Namepyrroline-hydroxy-carboxylate
CAS Registry NumberNot Available
SMILES
OC1CC(N=C1)C(O)=O
InChI Identifier
InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)
InChI KeyWFOFKRKDDKGRIK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids and derivatives  
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
    • 

  • Pyrroline carboxylic acid
    • 

  • Pyrroline carboxylic acid or derivatives
    • 

  • Pyrroline
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Imine
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.1ALOGPS
logP-1.5ChemAxon
logS-0.58ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)2.59ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.85 m³·mol⁻¹ChemAxon
Polarizability11.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001369  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022582  
KNApSAcK IDNot Available
Chemspider ID1030  
KEGG Compound IDC04281  
BioCyc IDNot Available
BiGG ID43511  
Wikipedia LinkNot Available
METLIN ID6196  
PubChem Compound1059  
PDB IDNot Available
ChEBI ID27391  
Good Scents IDNot Available
References
General References