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Showing NP-Card for (r)-timonacic (NP0243639)

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Record Information
Version2.0
Created at2022-09-07 04:14:11 UTC
Updated at2022-09-07 04:14:11 UTC
NP-MRD IDNP0243639
Secondary Accession NumbersNone
Natural Product Identification
Common Name(r)-timonacic
DescriptionThioproline, also known as gamma-thioproline or heparegen, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Thioproline is a very strong basic compound (based on its pKa). (r)-timonacic is found in Trypanosoma brucei. (r)-timonacic was first documented in 1957 (PMID: 13449082). An optically active version of thioproline having L-configuration (PMID: 13621285) (PMID: 2500398).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0243639 ((r)-timonacic)


  Mrv1652309191921462D          

  8  8  0  0  0  0            999 V2000
10000.682310000.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3973 9999.7677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.682310001.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.297510000.2623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6301 9999.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8850 9998.9927    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7100 9998.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9649 9999.7773    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
  7  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  1  1  6  0  0  0
M  END
Download

3D MOL for NP0243639 ((r)-timonacic)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    1.1229   -2.0614    0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2938   -1.0967    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -0.8682   -0.4405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853   -0.2345   -0.4475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3954    1.2179    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3383    1.7993   -0.1997 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1106    0.1350   -0.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214   -0.6919    0.1553 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3068   -0.4396    0.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -0.2380   -1.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779    1.7416   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.2601    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9376    0.1504    0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235   -0.0993   -1.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9469   -0.5747    1.1907 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 NP0243639 ((r)-timonacic)


  Mrv1652309191921462D          

  8  8  0  0  0  0            999 V2000
10000.682310000.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3973 9999.7677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.682310001.0035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.297510000.2623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6301 9999.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8850 9998.9927    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7100 9998.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9649 9999.7773    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
  7  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  1  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0243639

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H]1CSCN1

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1

> <INCHI_KEY>
DZLNHFMRPBPULJ-VKHMYHEASA-N

> <FORMULA>
C4H7NO2S

> <MOLECULAR_WEIGHT>
133.169

> <EXACT_MASS>
133.019749163

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.475369946394133

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-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>
2.591570198009273

> <JCHEM_PKA_STRONGEST_BASIC>
7.699494899219353

> <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>
(4R)-1,3-thiazolidine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0243639 ((r)-timonacic)

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PDB for NP0243639 ((r)-timonacic)
HEADER    PROTEIN                                 19-SEP-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-SEP-19         0                                  
HETATM    1  C   UNK     0    8667.9408667.001   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8669.2758666.233   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8667.9408668.540   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0    8665.3558667.156   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8664.1108666.251   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0    8664.5858664.786   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0    8666.1258664.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.6018666.251   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    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    8    6                                                       
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 NP0243639 ((r)-timonacic)
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SMILES for NP0243639 ((r)-timonacic)
OC(=O)[C@@H]1CSCN1
Download
INCHI for NP0243639 ((r)-timonacic)
InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
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View in JSmol
Synonyms
ValueSource
(4R)-4-Thiazolidinecarboxylic acidChEBI
(R)-(-)-4-Thiazolidinecarboxylic acidChEBI
(R)-4-Thiazolidinecarboxylic acidChEBI
4-ThiaprolineChEBI
gamma-ThioprolineChEBI
L-ThiaprolineChEBI
L-Thiazolidine-4-carboxylic acidChEBI
Thiazolidinecarboxylic acidChEBI
(4R)-4-ThiazolidinecarboxylateGenerator
(R)-(-)-4-ThiazolidinecarboxylateGenerator
(R)-4-ThiazolidinecarboxylateGenerator
g-ThioprolineGenerator
Γ-thioprolineGenerator
L-Thiazolidine-4-carboxylateGenerator
ThiazolidinecarboxylateGenerator
L-4-Thiazolidinecarboxylic acidHMDB
gamma-ThiaprolineHMDB
ThiaprolineHMDB
Thiazolidine-4-carboxylic acidHMDB
HeparegenHMDB
NorgamemHMDB
Thiazolidine-4-carboxylic acid, sodium saltHMDB
Thiazolidine-4-carboxylic acid, (R)-isomerHMDB
ThioprolineMeSH
Chemical FormulaC4H7NO2S
Average Mass133.1690 Da
Monoisotopic Mass133.01975 Da
IUPAC Name(4R)-1,3-thiazolidine-4-carboxylic acid
Traditional Name(4R)-1,3-thiazolidine-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)[C@@H]1CSCN1
InChI Identifier
InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
InChI KeyDZLNHFMRPBPULJ-VKHMYHEASA-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 l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentL-alpha-amino acids  
Alternative Parents
Substituents
  • L-alpha-amino acid
    • 

  • Thiazolidine
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Secondary amine
    • 

  • Thioether
    • 

  • Hemithioaminal
    • 

  • Dialkylthioether
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxygen 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
Polarizability12.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062164  
DrugBank IDDB02846  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD0-1571  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound93176  
PDB IDNot Available
ChEBI ID45171  
Good Scents IDNot Available
References
General References
  1. MACKENZIE CG, HARRIS J: N-formylcysteine synthesis in mitochondria from formaldehyde and L-cysteine via thiazolidinecarboxylic acid. J Biol Chem. 1957 Jul;227(1):393-406. [PubMed:13449082  ] 
  2. DEBEY HJ, MACKENZIE JB, MACKENZIE CG: The replacement by thiazolidinecarboxylic acid of exogenous cystine and cysteine. J Nutr. 1958 Dec 10;66(4):607-19. doi: 10.1093/jn/66.4.607. [PubMed:13621285  ] 
  3. Bohler S, Wagner K, Bassler KH: [Metabolism of L-thiazolidine-4-carboxylic acid]. Infusionstherapie. 1989 Apr;16(2):82-6. [PubMed:2500398  ] 
  4. LOTUS database [Link]