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Showing NP-Card for (1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate (NP0192042)

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Record Information
Version2.0
Created at2022-09-04 09:09:48 UTC
Updated at2022-09-04 09:09:48 UTC
NP-MRD IDNP0192042
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate
DescriptionMethyl (1S,4R)-1-oxo-1λ⁴,2-dithiolane-4-carboxylate belongs to the class of organic compounds known as 1,2-dithiolanes. These are organic compounds containing a 1,2-dithiolane ring. 1,2-Dithiolane moiety is a 5-membered saturated aliphatic ring with three carbon atoms, and two sulfur atoms at the 1- and 2- ring positions. (1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate is found in Asparagus officinalis. Based on a literature review very few articles have been published on methyl (1S,4R)-1-oxo-1λ⁴,2-dithiolane-4-carboxylate.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0192042 ((1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate)


  Mrv1652309042211092D          

 10 10  0  0  1  0            999 V2000
    1.2822    3.1768    0.0000 C   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
    0.5678    1.9393    0.0000 C   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
    0.5678    1.1143    0.0000 C   0  0  2  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 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 S   0  3  2  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  5  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
M  CHG  2   8   1   9  -1
M  END
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3D MOL for NP0192042 ((1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    3.1141   -0.3623   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8899    0.2188   -0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224   -0.5497   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8075   -1.7489   -0.3805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.0340    0.4245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6162   -1.0248    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -0.1617    0.6499 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4881    1.7703    0.1326 S   0  0  0  0  0  3  0  0  0  0  0  0
   -3.3393    2.3778   -1.1726 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9082    1.1598   -0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757   -1.3703   -0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4958    0.2898   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8725   -0.3730    0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323    0.3469    1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4845   -1.7011    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6319   -1.5762   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1378    1.9196   -0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0585    0.7511   -1.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  1
  6 15  1  0
  6 16  1  0
 10 17  1  0
 10 18  1  0
M  CHG  2   8   1   9  -1
M  END
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3D SDF for NP0192042 ((1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate)


  Mrv1652309042211092D          

 10 10  0  0  1  0            999 V2000
    1.2822    3.1768    0.0000 C   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
    0.5678    1.9393    0.0000 C   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
    0.5678    1.1143    0.0000 C   0  0  2  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 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 S   0  3  2  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  5  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
M  CHG  2   8   1   9  -1
M  END
> <DATABASE_ID>
NP0192042

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1CS[S@+]([O-])C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3S2/c1-8-5(6)4-2-9-10(7)3-4/h4H,2-3H2,1H3/t4-,10+/m1/s1

> <INCHI_KEY>
LSFPPLMNEFCRDI-KNODYTOMSA-N

> <FORMULA>
C5H8O3S2

> <MOLECULAR_WEIGHT>
180.24

> <EXACT_MASS>
179.991486466

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
16.73919795112671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate

> <JCHEM_LOGP>
-1.1274138745426119

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.922846693599877

> <JCHEM_PKA_STRONGEST_BASIC>
-5.894346856219415

> <JCHEM_POLAR_SURFACE_AREA>
49.36

> <JCHEM_REFRACTIVITY>
40.248200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0192042 ((1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate)

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PDB for NP0192042 ((1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       1.830  -0.290   0.000  0.00  0.00           S+0
HETATM    8  S   UNK     0       0.290  -0.290   0.000  0.00  0.00           S+1
HETATM    9  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O-1
HETATM   10  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0192042 ((1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate)
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SMILES for NP0192042 ((1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate)
COC(=O)[C@@H]1CS[S@+]([O-])C1
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INCHI for NP0192042 ((1s,4r)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate)
InChI=1S/C5H8O3S2/c1-8-5(6)4-2-9-10(7)3-4/h4H,2-3H2,1H3/t4-,10+/m1/s1
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View in JSmol
Synonyms
ValueSource
Methyl (1S,4R)-1-oxo-1,2-dithiolane-4-carboxylic acidGenerator
Chemical FormulaC5H8O3S2
Average Mass180.2400 Da
Monoisotopic Mass179.99149 Da
IUPAC Name(1S,4R)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate
Traditional Name(1S,4R)-4-(methoxycarbonyl)-1,2-dithiolan-1-ium-1-olate
CAS Registry NumberNot Available
SMILES
COC(=O)[C@@H]1CS[S@+]([O-])C1
InChI Identifier
InChI=1S/C5H8O3S2/c1-8-5(6)4-2-9-10(7)3-4/h4H,2-3H2,1H3/t4-,10+/m1/s1
InChI KeyLSFPPLMNEFCRDI-KNODYTOMSA-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
Asparagus officinalisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-dithiolanes. These are organic compounds containing a 1,2-dithiolane ring. 1,2-Dithiolane moiety is a 5-membered  saturated aliphatic ring with three carbon atoms, and two sulfur atoms at the 1- and 2- ring positions.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDithiolanes  
Sub Class1,2-dithiolanes  
Direct Parent1,2-dithiolanes  
Alternative Parents
Substituents
  • Methyl ester
    • 

  • 1,2-dithiolane
    • 

  • Thiosulfinic acid ester
    • 

  • Carboxylic acid ester
    • 

  • Sulfinyl compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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-1.1ChemAxon
pKa (Strongest Acidic)7.92ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.25 m³·mol⁻¹ChemAxon
Polarizability16.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
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 Compound163082546  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]