NP-MRD: Showing NP-Card for 5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium (NP0234947)

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Record Information

Version

2.0

Created at

2022-09-06 17:18:17 UTC

Updated at

2022-09-06 17:18:17 UTC

NP-MRD ID

NP0234947

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium

Description

Reticulatin B belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group. 5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium is found in Fascaplysinopsis reticulata. Based on a literature review very few articles have been published on Reticulatin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    2.9202   -2.9602   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2771   -1.6253   -0.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643   -1.2263    0.9933 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3838    0.3711    0.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8126    0.6772    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596   -0.2733   -0.4464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4419   -1.5868   -0.1657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -2.3579   -1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642   -0.0172   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4992    0.6830    0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1684   -0.6073   -0.7717 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9891    1.9983    0.1773 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.1007    2.8055   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0759    2.5301    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9158    1.5486    1.1475 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791    1.7804    1.8417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823   -3.5444    0.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9322   -3.5309   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9508   -2.8557    0.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -1.5899   -1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -0.8492   -0.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7775   -0.1467   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0280   -3.3859   -1.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072   -2.3351   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946   -1.9162   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434    3.2341    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6636    2.2665   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    3.6919   -0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2325    3.6055    0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474    2.0657    2.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8216    0.9020    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.6484    1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 11  1  0
  9 10  2  0
  5 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  6 22  1  6
  8 23  1  0
  8 24  1  0
  8 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  CHG  2  11  -1  12   1
M  END


  Mrv1652309062219182D          

 16 16  0  0  1  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 S   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
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    2.2433    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  3  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
    0.1553   -0.1553    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
   -0.8843    0.8843    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  CHG  2  11  -1  12   1
M  END
> <DATABASE_ID>
NP0234947

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCSC1=C([C@@H](OC)C([O-])=O)[N+](C)=CN1C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O3S/c1-5-16-9-7(8(15-4)10(13)14)11(2)6-12(9)3/h6,8H,5H2,1-4H3/t8-/m1/s1

> <INCHI_KEY>
OONRYSCSFGQITJ-MRVPVSSYSA-N

> <FORMULA>
C10H16N2O3S

> <MOLECULAR_WEIGHT>
244.31

> <EXACT_MASS>
244.088163557

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.133738120090573

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(R)-carboxy(methoxy)methyl]-5-(ethylsulfanyl)-1,3-dimethyl-1H-imidazol-3-ium

> <JCHEM_LOGP>
-3.013620867805079

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.146249942478296

> <JCHEM_PKA_STRONGEST_BASIC>
-4.257797274890113

> <JCHEM_POLAR_SURFACE_AREA>
58.17

> <JCHEM_REFRACTIVITY>
73.77430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(R)-carboxy(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       1.060   3.620   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.915   0.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.379   1.096   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.091   3.157   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.555   3.633   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.946   4.188   0.000  0.00  0.00           O-1
HETATM   12  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+1
HETATM   13  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    4   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆N₂O₃S

Average Mass

244.3100 Da

Monoisotopic Mass

244.08816 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCSC1=C([C@@H](OC)C([O-])=O)[N+](C)=CN1C

InChI Identifier

InChI=1S/C10H16N2O3S/c1-5-16-9-7(8(15-4)10(13)14)11(2)6-12(9)3/h6,8H,5H2,1-4H3/t8-/m1/s1

InChI Key

OONRYSCSFGQITJ-MRVPVSSYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fascaplysinopsis reticulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Aryl thioethers

Alternative Parents

Substituents

Aryl thioether
Alkylarylthioether
N-substituted imidazole
Azole
Imidazole
Heteroaromatic compound
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Sulfenyl compound
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organic salt
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102105745

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium (NP0234947)

MOL for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

3D MOL for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

3D SDF for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

3D-SDF for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

PDB for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

3D PDB for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

SMILES for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

INCHI for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

Structure for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)

3D Structure for NP0234947 (5-[(r)-carboxylato(methoxy)methyl]-4-(ethylsulfanyl)-1,3-dimethylimidazol-1-ium)