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Showing NP-Card for (2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid (NP0192743)

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Record Information
Version2.0
Created at2022-09-04 10:01:38 UTC
Updated at2022-09-04 10:01:38 UTC
NP-MRD IDNP0192743
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid
Description(3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic acid, also known as 3-hydroxy-L-1-pyrroline-5-carboxylate, belongs to the class of organic compounds known as alpha amino acids and derivatives. (2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid is found in Trypanosoma brucei. 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 (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylic acid is a moderately basic compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0192743 ((2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid)


  Mrv1652303231705332D          

 11 11  0  0  1  0            999 V2000
   -0.1673    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   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  2  0  0  0  0  0  0  0  0  0
    0.6057   -0.8903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  5  9  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
Download

3D MOL for NP0192743 ((2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.4545   -1.5671   -0.7172 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9902   -0.4435   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8657    0.5092    0.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5692   -0.0632   -0.5202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0886    0.2277    0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5608   -0.0162    0.4340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1183    1.0557   -0.2153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021   -1.1353   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340   -1.1273   -1.0508 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5597    1.3853    0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227    0.8230   -1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069   -0.5668    1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801    1.2332    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534   -0.2954    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973    1.8029   -0.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1945   -1.8223   -0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  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
  6 14  1  1
  7 15  1  0
  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 NP0192743 ((2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid)


  Mrv1652303231705332D          

 11 11  0  0  1  0            999 V2000
   -0.1673    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   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  2  0  0  0  0  0  0  0  0  0
    0.6057   -0.8903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  5  9  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0192743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(O)C[C@]([H])(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)/t3-,4+/m1/s1

> <INCHI_KEY>
WFOFKRKDDKGRIK-DMTCNVIQSA-N

> <FORMULA>
C5H7NO3

> <MOLECULAR_WEIGHT>
129.115

> <EXACT_MASS>
129.042593089

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.586908286410658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-1.4545071951925137

> <ALOGPS_LOGS>
-0.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.254837388721942

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7212230695209163

> <JCHEM_PKA_STRONGEST_BASIC>
2.5899435587205404

> <JCHEM_POLAR_SURFACE_AREA>
69.89000000000001

> <JCHEM_REFRACTIVITY>
28.8459

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0192743 ((2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid)

Download
PDB for NP0192743 ((2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid)
HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0      -0.312   2.779   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       1.131  -1.662   0.000  0.00  0.00           H+0
HETATM    7  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.267  -1.375   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.109  -2.943   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    8                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    9                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    2                                                       
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0192743 ((2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid)
Download
SMILES for NP0192743 ((2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid)
[H][C@@]1(O)C[C@]([H])(N=C1)C(O)=O
Download
INCHI for NP0192743 ((2s,4r)-4-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid)
InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)/t3-,4+/m1/s1
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View in JSmol
Synonyms
ValueSource
(3R,5S)-1-Pyrroline-3-hydroxy-5-carboxylateChEBI
3-Hydroxy-L-1-pyrroline-5-carboxylateChEBI
L-1-Pyrroline-3-hydroxy-5-carboxylateChEBI
(3R,5S)-3-Hydroxy-1-pyrroline-5-carboxylateKegg
3-Hydroxy-L-1-pyrroline-5-carboxylic acidGenerator
L-1-Pyrroline-3-hydroxy-5-carboxylic acidGenerator
(3R,5S)-3-Hydroxy-1-pyrroline-5-carboxylic acidGenerator
Chemical FormulaC5H7NO3
Average Mass129.1150 Da
Monoisotopic Mass129.04259 Da
IUPAC Name(2S,4R)-4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid
Traditional Name(2S,4R)-4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(O)C[C@]([H])(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)/t3-,4+/m1/s1
InChI KeyWFOFKRKDDKGRIK-DMTCNVIQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Trypanosoma bruceiLOTUS Database
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
Polarizability11.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062585  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04281  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11966267  
PDB IDNot Available
ChEBI ID6151  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]