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Showing NP-Card for l-thioproline (NP0153334)

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Record Information
Version2.0
Created at2022-09-02 09:58:36 UTC
Updated at2022-09-02 09:58:36 UTC
NP-MRD IDNP0153334
Secondary Accession NumbersNone
Natural Product Identification
Common Namel-thioproline
DescriptionTimonacic, also known as DL-thiaproline or hepacom, 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. A sulfur-containing amino acid that is proline in which the methylene group at position 4 is replaced by a sulfur atom. l-thioproline is found in Arabidopsis thaliana, Caenorhabditis elegans and Lentinula edodes. Timonacic is a very strong basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0153334 (l-thioproline)


  Mrv0541 01301517062D          

  8  8  0  0  0  0            999 V2000
    1.2352    0.6294    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
    0.5678    1.1143    0.0000 C   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
   -0.0997    0.6294    0.0000 N   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
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
M  END
Download

3D MOL for NP0153334 (l-thioproline)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    1.9338   -0.9846   -1.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6246   -0.0645   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321    0.5385    0.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122    0.3615   -0.1822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1238    0.2610    1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594    0.3239    1.1404 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -0.4537   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456   -0.3779   -0.9844 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511    0.0528    0.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1856    1.4571   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656    1.1176    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0924   -0.7183    1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -1.5379   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376   -0.0018   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513    0.0263   -1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  3  9  1  0
  4 10  1  6
  5 11  1  0
  5 12  1  0
  7 13  1  0
  7 14  1  0
  8 15  1  0
M  END
Download

3D SDF for NP0153334 (l-thioproline)


  Mrv0541 01301517062D          

  8  8  0  0  0  0            999 V2000
    1.2352    0.6294    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
    0.5678    1.1143    0.0000 C   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
   -0.0997    0.6294    0.0000 N   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
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CSCN1

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)

> <INCHI_KEY>
DZLNHFMRPBPULJ-UHFFFAOYSA-N

> <FORMULA>
C4H7NO2S

> <MOLECULAR_WEIGHT>
133.17

> <EXACT_MASS>
133.019749643

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.465868541265749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-thiazolidine-4-carboxylic acid

> <ALOGPS_LOGP>
-2.47

> <JCHEM_LOGP>
-2.682584780794309

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.591570198009271

> <JCHEM_PKA_STRONGEST_BASIC>
7.699494899219355

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
30.8241

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-thioproline

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0153334 (l-thioproline)

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PDB for NP0153334 (l-thioproline)
HEADER    PROTEIN                                 30-JAN-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JAN-15         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       1.830  -0.290   0.000  0.00  0.00           S+0
CONECT    1    3    8                                                       
CONECT    2    5    8                                                       
CONECT    3    1    4    5                                                  
CONECT    4    3    6    7                                                  
CONECT    5    2    3                                                       
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    1    2                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0153334 (l-thioproline)
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SMILES for NP0153334 (l-thioproline)
OC(=O)C1CSCN1
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INCHI for NP0153334 (l-thioproline)
InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)
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View in JSmol
Synonyms
ValueSource
4-CarboxythiazolidineChEBI
4-Thiazolidinecarboxylic acidChEBI
Acide DL thiazolidine carboxylique-4ChEBI
Acide thiazolidine-4-carboxyliqueChEBI
DL-ThiaprolineChEBI
DL-Thiazolidinecarboxylic acidChEBI
ThiaprolineChEBI
Thiazolidine-4-carboxylic acidChEBI
Thiazolidinecarboxylic acidChEBI
TimonacicoChEBI
TimonacicumChEBI
HepacomKegg
4-ThiazolidinecarboxylateGenerator
DL-ThiazolidinecarboxylateGenerator
Thiazolidine-4-carboxylateGenerator
ThiazolidinecarboxylateGenerator
TimonacicChEBI
HeparegenMeSH
gamma-ThiaprolineMeSH
NorgamemMeSH
Thiazolidine-4-carboxylic acid, (R)-isomerMeSH
Thiazolidine-4-carboxylic acid, sodium saltMeSH
Chemical FormulaC4H7NO2S
Average Mass133.1700 Da
Monoisotopic Mass133.01975 Da
IUPAC Name1,3-thiazolidine-4-carboxylic acid
Traditional NameL-thioproline
CAS Registry NumberNot Available
SMILES
OC(=O)C1CSCN1
InChI Identifier
InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)
InChI KeyDZLNHFMRPBPULJ-UHFFFAOYSA-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
Arabidopsis thalianaLOTUS Database
Caenorhabditis elegansLOTUS Database
Lentinus edodesLOTUS 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
    • 

  • Thiazolidine
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Secondary amine
    • 

  • Thioether
    • 

  • Hemithioaminal
    • 

  • Dialkylthioether
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • 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-2.5ALOGPS
logP-2.7ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)2.59ChemAxon
pKa (Strongest Basic)7.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.82 m³·mol⁻¹ChemAxon
Polarizability12.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB12856  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9934  
PDB IDNot Available
ChEBI ID64564  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]