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Showing metabocard for 1-Pyrroline-5-carboxylic acid (HMDB0001301)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:35 UTC
HMDB IDHMDB0001301
Secondary Accession Numbers
  • HMDB0002240
  • HMDB01301
  • HMDB02240
Metabolite Identification
Common Name1-Pyrroline-5-carboxylic acid
Description1-Pyrroline-5-carboxylic acid (CAS: 2906-39-0) is an enamine or an imino acid that forms upon the spontaneous dehydration of L-glutamate gamma-semialdehyde in aqueous solutions. The stereoisomer (S)-1-pyrroline-5-carboxylate is an intermediate in glutamate metabolism, arginine degradation, and proline biosynthesis and degradation. It can also be converted into or be formed from three amino acids: L-glutamate, L-ornithine, and L-proline. In particular, it is synthesized via the oxidation of proline by pyrroline-5-carboxylate reductase 1 (PYCR1) (EC 1.5.1.2) or by proline dehydrogenase (PRODH) (EC 1.5.99.8). It is hydrolyzed into L-glutamate by delta-1-pyrroline-5-carboxylate dehydrogenase (ALDH4A1) (EC 1.5.1.12). It is also one of the few metabolites that can act as a precursor to other metabolites of both the urea cycle and the tricarboxylic acid (TCA) cycle. Under certain conditions, pyrroline-5-carboxylate can act as a neurotoxin and a metabotoxin. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of pyrroline-5-carboxylate are associated with at least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency. Hyperprolinemia type II results in high levels of pyrroline-5-carboxylate. People with hyperprolinemia type II have signs and symptoms that vary in severity, but they are more likely than type I to have seizures or intellectual disability. Pyrroline-5-carboxylate is highly reactive and excess quantities have been shown to cause cell death and apoptosis (PMID: 15548746 ).
Structure
Data?1676999735
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001301 (1-Pyrroline-5-carboxylic acid)


  Mrv1652309142020202D          

  8  8  0  0  0  0            999 V2000
    0.6685    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -0.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6685    1.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162    0.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3836   -0.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488   -0.2207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4  8  1  0  0  0  0
  8  1  1  6  0  0  0
M  END
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3D MOL for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

HMDB0001301
     RDKit          3D
1-Pyrroline-5-carboxylic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
    1.6190    1.4570    1.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6296    0.3445    0.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678   -0.1099    0.3681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718   -0.3699    0.6288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0319   -0.5351   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -0.6820   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    0.2155    0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7091    0.3588    1.1833 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1878   -0.0714   -0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516   -1.4052    1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550   -1.4759   -1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929    0.3317   -1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0870   -0.3509   -1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8072   -1.7096   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    0.7053    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  3  9  1  0
  4 10  1  1
  5 11  1  0
  5 12  1  0
  6 13  1  0
  6 14  1  0
  7 15  1  0
M  END
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3D SDF for HMDB0001301 (1-Pyrroline-5-carboxylic acid)


  Mrv1652309142020202D          

  8  8  0  0  0  0            999 V2000
    0.6685    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -0.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6685    1.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162    0.2642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3836   -0.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488   -0.2207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4  8  1  0  0  0  0
  8  1  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001301

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)[C@@H]1CCC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)/t4-/m0/s1

> <INCHI_KEY>
DWAKNKKXGALPNW-BYPYZUCNSA-N

> <FORMULA>
C5H7NO2

> <MOLECULAR_WEIGHT>
113.1146

> <EXACT_MASS>
113.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.721633827168107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3,4-dihydro-2H-pyrrole-2-carboxylic acid

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-2.279439073313947

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8219556318598356

> <JCHEM_PKA_STRONGEST_BASIC>
6.073045352102196

> <JCHEM_POLAR_SURFACE_AREA>
49.66

> <JCHEM_REFRACTIVITY>
27.397299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-1-pyrroline-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

HMDB0001301
     RDKit          3D
1-Pyrroline-5-carboxylic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
    1.6190    1.4570    1.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6296    0.3445    0.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678   -0.1099    0.3681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718   -0.3699    0.6288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0319   -0.5351   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -0.6820   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    0.2155    0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7091    0.3588    1.1833 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1878   -0.0714   -0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516   -1.4052    1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550   -1.4759   -1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1929    0.3317   -1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0870   -0.3509   -1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8072   -1.7096   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    0.7053    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  3  9  1  0
  4 10  1  1
  5 11  1  0
  5 12  1  0
  6 13  1  0
  6 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

HEADER    PROTEIN                                 14-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-SEP-20         0                                  
HETATM    1  C   UNK     0       1.248   0.338   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.583  -0.430   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       1.248   1.877   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -1.337   0.493   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.583  -0.412   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.107  -1.877   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.567  -1.877   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.091  -0.412   0.000  0.00  0.00           C+0
CONECT    1    2    3    8                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    5    8                                                       
CONECT    5    6    4                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    1                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

COMPND    HMDB0001301
HETATM    1  O1  UNL     1       1.619   1.457   1.388  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.630   0.344   0.803  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.868  -0.110   0.368  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.372  -0.370   0.629  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.032  -0.535  -0.819  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.534  -0.682  -0.672  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.782   0.216   0.497  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.709   0.359   1.183  1.00  0.00           N  
HETATM    9  H1  UNL     1       3.188  -0.071  -0.582  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.452  -1.405   1.048  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.355  -1.476  -1.260  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.193   0.332  -1.441  1.00  0.00           H  
HETATM   13  H5  UNL     1      -2.087  -0.351  -1.564  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.807  -1.710  -0.351  1.00  0.00           H  
HETATM   15  H7  UNL     1      -2.724   0.705   0.773  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    8   10
CONECT    5    6   11   12
CONECT    6    7   13   14
CONECT    7    8    8   15
END
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SMILES for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

OC(=O)[C@@H]1CCC=N1
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INCHI for HMDB0001301 (1-Pyrroline-5-carboxylic acid)

InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)/t4-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-Pyrroline-5-carboxylateChEBI, KEGG
L-1-Pyrroline-5-carboxylateChEBI, KEGG
1-Pyrroline-5-carboxylic acidGenerator
(S)-1-Pyrroline-5-carboxylic acidGenerator
L-1-Pyrroline-5-carboxylic acidGenerator
delta-1-Pyrroline-5-carboxylateMeSH
delta-1-Pyrroline-5-carboxylate, (+-)-isomerMeSH
delta-1-Pyrroline-5-carboxylic acidMeSH
delta-1-Pyrroline-5-carboxylate, 14C-labeled, (+-)-isomerMeSH
delta(1)Pyrroline-5-carboxylateMeSH
Pyrroline-5-carboxylateMeSH
(2S)-3,4-Dihydro-2H-pyrrole-2-carboxylic acidHMDB
(S)-1-Pyrroline-5-carboxylateHMDB
3,4-Dihydro-2H-pyrrole-2-carboxylic acidHMDB
delta1-Pyrroline-5-carboxylic acidHMDB
Δ1-Pyrroline-5-carboxylic acidHMDB
Chemical FormulaC5H7NO2
Average Molecular Weight113.1146
Monoisotopic Molecular Weight113.047678473
IUPAC Name(2S)-3,4-dihydro-2H-pyrrole-2-carboxylic acid
Traditional NameL-1-pyrroline-5-carboxylate
CAS Registry Number64199-88-8
SMILES
OC(=O)[C@@H]1CCC=N1
InChI Identifier
InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)/t4-/m0/s1
InChI KeyDWAKNKKXGALPNW-BYPYZUCNSA-N
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
  • 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
  • Carbonyl group
  • Imine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
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
Water Solubility13.1 g/LALOGPS
logP-0.01ALOGPS
logP-2.3ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)6.07ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.4 m³·mol⁻¹ChemAxon
Polarizability10.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+119.17130932474
DeepCCS[M-H]-115.48430932474
DeepCCS[M-2H]-152.81930932474
DeepCCS[M+Na]+127.81930932474
AllCCS[M+H]+124.932859911
AllCCS[M+H-H2O]+120.132859911
AllCCS[M+NH4]+129.532859911
AllCCS[M+Na]+130.832859911
AllCCS[M-H]-120.232859911
AllCCS[M+Na-2H]-122.732859911
AllCCS[M+HCOO]-125.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.79 minutes32390414
Predicted by Siyang on May 30, 20228.6329 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.43 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid292.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid707.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid314.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid78.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid207.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid72.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid253.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid270.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)378.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid595.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid120.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid737.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid194.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid212.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate649.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA305.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water265.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Pyrroline-5-carboxylic acidOC(=O)[C@@H]1CCC=N11722.0Standard polar33892256
1-Pyrroline-5-carboxylic acidOC(=O)[C@@H]1CCC=N11045.2Standard non polar33892256
1-Pyrroline-5-carboxylic acidOC(=O)[C@@H]1CCC=N11076.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Pyrroline-5-carboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]1CCC=N11116.5Semi standard non polar33892256
1-Pyrroline-5-carboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCC=N11365.1Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Feces
Tissue Locations
  • Intestine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030153
KNApSAcK IDC00007606
Chemspider ID389153
KEGG Compound IDC03912
BioCyc IDL-DELTA1-PYRROLINE_5-CARBOXYLATE
BiGG IDNot Available
Wikipedia Link1-Pyrroline-5-carboxylic acid
METLIN IDNot Available
PubChem Compound440162
PDB IDNot Available
ChEBI ID371
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceVogel, Henry J.; Davis, Bernard D. Glutamic g-semialdehyde and D1-pyrroline-5-carboxylic acid, intermediates in the biosynthesis of proline. Journal of the American Chemical Society (1952), 74 109-12.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simila S: Hydroxyproline metabolism in type II hyperprolinaemia. Ann Clin Biochem. 1979 Jul;16(4):177-81. [PubMed:533224 ]
  2. Humbertclaude V, Rivier F, Roubertie A, Echenne B, Bellet H, Vallat C, Morin D: Is hyperprolinemia type I actually a benign trait? Report of a case with severe neurologic involvement and vigabatrin intolerance. J Child Neurol. 2001 Aug;16(8):622-3. [PubMed:11510941 ]
  3. Mixson AJ, Phang JM: The uptake of pyrroline 5-carboxylate. Group translocation mediating the transfer of reducing-oxidizing potential. J Biol Chem. 1988 Aug 5;263(22):10720-4. [PubMed:3392037 ]
  4. Wakabayashi Y: Tissue-selective expression of enzymes of arginine synthesis. Curr Opin Clin Nutr Metab Care. 1998 Jul;1(4):335-9. [PubMed:10565370 ]
  5. Onenli-Mungan N, Yuksel B, Elkay M, Topaloglu AK, Baykal T, Ozer G: Type II hyperprolinemia: a case report. Turk J Pediatr. 2004 Apr-Jun;46(2):167-9. [PubMed:15214748 ]
  6. Fleming GA, Hagedorn CH, Granger AS, Phang JM: Pyrroline-5-carboxylate in human plasma. Metabolism. 1984 Aug;33(8):739-42. [PubMed:6748947 ]
  7. Deuschle K, Funck D, Forlani G, Stransky H, Biehl A, Leister D, van der Graaff E, Kunze R, Frommer WB: The role of [Delta]1-pyrroline-5-carboxylate dehydrogenase in proline degradation. Plant Cell. 2004 Dec;16(12):3413-25. doi: 10.1105/tpc.104.023622. Epub 2004 Nov 17. [PubMed:15548746 ]

Enzymes

Enzyme Details
1. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes.
Gene Name:
ALDH4A1
Uniprot ID:
P30038
Molecular weight:
55117.24
Reactions
1-Pyrroline-5-carboxylic acid + NAD(P)(+) + Water → Glutamic acid + NAD(P)Hdetails
1-Pyrroline-5-carboxylic acid + NAD + Water → Glutamic acid + NADH + Hydrogen Iondetails
1-Pyrroline-5-carboxylic acid + NADP + Water → Glutamic acid + NADPH + Hydrogen Iondetails
Enzyme Details
2. Pyrroline-5-carboxylate reductase 1, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Housekeeping enzyme that catalyzes the last step in proline biosynthesis. Can utilize both NAD and NADP, but has higher affinity for NAD. Involved in the cellular response to oxidative stress.
Gene Name:
PYCR1
Uniprot ID:
P32322
Molecular weight:
33360.27
Reactions
Proline + NAD(P)(+) → 1-Pyrroline-5-carboxylic acid + NAD(P)Hdetails
Proline + NAD → 1-Pyrroline-5-carboxylic acid + NADH + Hydrogen Iondetails
Proline + NADP → 1-Pyrroline-5-carboxylic acid + NADPH + Hydrogen Iondetails
Enzyme Details
3. Pyrroline-5-carboxylate reductase 2
General function:
Involved in oxidoreductase activity
Specific function:
Housekeeping enzyme that catalyzes the last step in proline biosynthesis. In some cell types, such as erythrocytes, its primary function may be the generation of NADP(+). Can utilize both NAD and NADP. Has higher affinity for NADP, but higher catalytic efficiency with NADH.
Gene Name:
PYCR2
Uniprot ID:
Q96C36
Molecular weight:
25867.975
Reactions
Proline + NAD(P)(+) → 1-Pyrroline-5-carboxylic acid + NAD(P)Hdetails
Proline + NAD → 1-Pyrroline-5-carboxylic acid + NADH + Hydrogen Iondetails
Proline + NADP → 1-Pyrroline-5-carboxylic acid + NADPH + Hydrogen Iondetails
Enzyme Details
4. Proline dehydrogenase 1, mitochondrial
General function:
Involved in proline dehydrogenase activity
Specific function:
Converts proline to delta-1-pyrroline-5-carboxylate.
Gene Name:
PRODH
Uniprot ID:
O43272
Molecular weight:
56196.675
Reactions
Proline + acceptor → 1-Pyrroline-5-carboxylic acid + reduced acceptordetails
Proline + Acceptor → 1-Pyrroline-5-carboxylic acid + Reduced acceptordetails
Enzyme Details
5. Pyrroline-5-carboxylate reductase 3
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
PYCRL
Uniprot ID:
Q53H96
Molecular weight:
29892.415
Reactions
Proline + NAD(P)(+) → 1-Pyrroline-5-carboxylic acid + NAD(P)Hdetails
Proline + NAD → 1-Pyrroline-5-carboxylic acid + NADH + Hydrogen Iondetails
Proline + NADP → 1-Pyrroline-5-carboxylic acid + NADPH + Hydrogen Iondetails
Enzyme Details
6. Probable proline dehydrogenase 2
General function:
Involved in proline dehydrogenase activity
Specific function:
Converts proline to delta-1-pyrroline-5-carboxylate (Probable).
Gene Name:
PRODH2
Uniprot ID:
Q9UF12
Molecular weight:
58870.115
Reactions
Proline + acceptor → 1-Pyrroline-5-carboxylic acid + reduced acceptordetails