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Showing NP-Card for [(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium (NP0233219)

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Record Information
Version2.0
Created at2022-09-06 14:44:30 UTC
Updated at2022-09-06 14:44:30 UTC
NP-MRD IDNP0233219
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium
DescriptionGonyauline belongs to the class of organic compounds known as cyclopropanecarboxylic acids. These are organic compounds containing a carboxyl group attached to a cyclopropane ring. [(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium is found in Lingulodinium polyedra. [(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium was first documented in 1991 (PMID: 1999237). Based on a literature review very few articles have been published on Gonyauline.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0233219 ([(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium)


  Mrv1652309062216442D          

  9  9  0  0  1  0            999 V2000
    0.9526    2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    1.7138    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
   -0.4763    2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8888   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    0.1743    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  CHG  2   2   1   9  -1
M  END
Download

3D MOL for NP0233219 ([(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -1.8079   -1.3799   -0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652    0.0762   -0.5877 S   0  0  0  0  0  3  0  0  0  0  0  0
   -1.8097    1.4319   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967   -0.2045    0.7397 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4110    0.8156    1.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8004   -0.5334    0.4281 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3434   -0.4150   -0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6154   -1.4428   -1.6117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809    0.8077   -1.5525 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0953   -1.6747    0.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023   -2.1887   -1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7338   -1.1928   -1.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447    1.2885    0.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988    2.3518   -0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576    1.5764   -0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0663   -0.7171    1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165    1.7077    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7160    0.9677    2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014   -1.2746    1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  6  4  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  1
  5 17  1  0
  5 18  1  0
  6 19  1  1
M  CHG  2   2   1   9  -1
M  END
Download

3D SDF for NP0233219 ([(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium)


  Mrv1652309062216442D          

  9  9  0  0  1  0            999 V2000
    0.9526    2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    1.7138    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
   -0.4763    2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8888   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    0.1743    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  CHG  2   2   1   9  -1
M  END
> <DATABASE_ID>
NP0233219

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O2S/c1-9(2)5-3-4(5)6(7)8/h4-5H,3H2,1-2H3/t4-,5+/m0/s1

> <INCHI_KEY>
BSFOBFUZLFYTEX-CRCLSJGQSA-N

> <FORMULA>
C6H10O2S

> <MOLECULAR_WEIGHT>
146.2

> <EXACT_MASS>
146.040150736

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.820071069184781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R)-2-carboxycyclopropyl]dimethylsulfanium

> <JCHEM_LOGP>
-0.4405701272092789

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.095942438388417

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
46.6357

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R)-2-carboxycyclopropyl]dimethylsulfanium

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0233219 ([(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium)

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PDB for NP0233219 ([(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.778   3.969   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       0.445   3.199   0.000  0.00  0.00           S+1
HETATM    3  C   UNK     0      -0.889   3.969   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.659  -0.445   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.659  -1.985   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.993   0.325   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4    6                                                       
CONECT    6    5    4    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0233219 ([(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium)
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SMILES for NP0233219 ([(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium)
C[S+](C)[C@@H]1C[C@@H]1C([O-])=O
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INCHI for NP0233219 ([(1r,2r)-2-carboxylatocyclopropyl]dimethylsulfanium)
InChI=1S/C6H10O2S/c1-9(2)5-3-4(5)6(7)8/h4-5H,3H2,1-2H3/t4-,5+/m0/s1
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View in JSmol
Synonyms
ValueSource
S-Methyl-cis-2-(methylthio)cyclopropanecarboxylic acidMeSH
Chemical FormulaC6H10O2S
Average Mass146.2000 Da
Monoisotopic Mass146.04015 Da
IUPAC Name[(1R,2R)-2-carboxycyclopropyl]dimethylsulfanium
Traditional Name[(1R,2R)-2-carboxycyclopropyl]dimethylsulfanium
CAS Registry NumberNot Available
SMILES
C[S+](C)[C@@H]1C[C@@H]1C([O-])=O
InChI Identifier
InChI=1S/C6H10O2S/c1-9(2)5-3-4(5)6(7)8/h4-5H,3H2,1-2H3/t4-,5+/m0/s1
InChI KeyBSFOBFUZLFYTEX-CRCLSJGQSA-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
Gonyaulax polyedraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclopropanecarboxylic acids. These are organic compounds containing a carboxyl group attached to a cyclopropane ring.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassCyclopropanecarboxylic acids and derivatives  
Direct ParentCyclopropanecarboxylic acids  
Alternative Parents
Substituents
  • Cyclopropanecarboxylic acid
    • 

  • Carboxylic acid salt
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic salt
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic cation
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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-0.44ChemAxon
pKa (Strongest Acidic)4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.64 m³·mol⁻¹ChemAxon
Polarizability14.82 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 ID2340372  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3083055  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Roenneberg T, Nakamura H, Cranmer LD 3rd, Ryan K, Kishi Y, Hastings JW: Gonyauline: a novel endogenous substance shortening the period of the circadian clock of a unicellular alga. Experientia. 1991 Jan 15;47(1):103-6. doi: 10.1007/BF02041268. [PubMed:1999237  ] 
  2. LOTUS database [Link]