NP-MRD: Showing NP-Card for Foetisulfide A (NP0026084)

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Record Information

Version

2.0

Created at

2021-06-19 18:02:08 UTC

Updated at

2021-06-29 23:51:24 UTC

NP-MRD ID

NP0026084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Foetisulfide A

Provided By

JEOL Database JEOL Logo

Description

Foetisulfide A is found in Ferula assa-foetida and Ferula foetida. Foetisulfide A was first documented in 2002 (Duan, H., et al.). Based on a literature review very few articles have been published on (2R)-2-{[(2E)-3-[(S)-methanesulfinyl]prop-2-en-1-yl]disulfanyl}butane.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120023D          

 28 27  0  0  0  0            999 V2000
    1.5180   -1.2367   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284   -0.9994    0.0016 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9127   -1.7133    1.3590 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3210   -1.6106    1.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -1.1651    2.5917 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147    0.7987    3.0169 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0376    1.7564    1.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3977    1.5944    2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3457    1.1205    1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163    0.9562    2.0843 S   0  0  2  0  0  4  0  0  0  0  0  0
   -2.7762   -0.6154    2.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8387    0.6633    0.8644 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -0.7630   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6633   -0.8180   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3411   -2.3069   -0.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    0.0766    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6395   -1.3697   -0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7060   -2.7778    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389   -0.5721    2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932   -2.1277    2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455   -2.0819    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3131    2.8117    1.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2224    1.4700    0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6489    1.8875    3.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1140    0.8467    0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3731   -1.3663    2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0963   -0.4693    3.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454   -0.9523    3.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
  6  5  1  0  0  0  0
  9  8  2  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
 10  9  1  0  0  0  0
 10 12  2  0  0  0  0
  7  6  1  0  0  0  0
  3  4  1  0  0  0  0
 11 26  1  0  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
  9 25  1  0  0  0  0
  8 24  1  0  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
  3 18  1  0  0  0  0
  2 16  1  0  0  0  0
  2 17  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
M  END


  Mrv1652306192120023D          

 28 27  0  0  0  0            999 V2000
    1.5180   -1.2367   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284   -0.9994    0.0016 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9127   -1.7133    1.3590 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3210   -1.6106    1.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -1.1651    2.5917 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147    0.7987    3.0169 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0376    1.7564    1.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3977    1.5944    2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3457    1.1205    1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163    0.9562    2.0843 S   0  0  2  0  0  4  0  0  0  0  0  0
   -2.7762   -0.6154    2.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8387    0.6633    0.8644 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -0.7630   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6633   -0.8180   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3411   -2.3069   -0.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    0.0766    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6395   -1.3697   -0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7060   -2.7778    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389   -0.5721    2.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932   -2.1277    2.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455   -2.0819    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3131    2.8117    1.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2224    1.4700    0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6489    1.8875    3.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1140    0.8467    0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3731   -1.3663    2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0963   -0.4693    3.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454   -0.9523    3.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
  6  5  1  0  0  0  0
  9  8  2  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
 10  9  1  0  0  0  0
 10 12  2  0  0  0  0
  7  6  1  0  0  0  0
  3  4  1  0  0  0  0
 11 26  1  0  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
  9 25  1  0  0  0  0
  8 24  1  0  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
  3 18  1  0  0  0  0
  2 16  1  0  0  0  0
  2 17  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C([H])([H])SS[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])[S@@](=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H16OS3/c1-4-8(2)11-10-6-5-7-12(3)9/h5,7-8H,4,6H2,1-3H3/b7-5+/t8-,12+/m1/s1

> <INCHI_KEY>
MRLXFQWCSNFUCF-RZXMPWAMSA-N

> <FORMULA>
C8H16OS3

> <MOLECULAR_WEIGHT>
224.4

> <EXACT_MASS>
224.036328657

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.82554830112365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-{[(2E)-3-[(S)-methanesulfinyl]prop-2-en-1-yl]disulfanyl}butane

> <ALOGPS_LOGP>
3.06

> <JCHEM_LOGP>
1.517611468333333

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.179542760569462

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
64.3697

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{[(2E)-3-[(S)-methanesulfinyl]prop-2-en-1-yl]disulfanyl}butane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.518  -1.237  -0.738  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.828  -0.999   0.002  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.913  -1.713   1.359  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.321  -1.611   1.946  0.00  0.00           C+0
HETATM    5  S   UNK     0       1.652  -1.165   2.592  0.00  0.00           S+0
HETATM    6  S   UNK     0       2.115   0.799   3.017  0.00  0.00           S+0
HETATM    7  C   UNK     0       1.038   1.756   1.900  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.398   1.594   2.298  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.346   1.121   1.475  0.00  0.00           C+0
HETATM   10  S   UNK     0      -3.016   0.956   2.084  0.00  0.00           S+0
HETATM   11  C   UNK     0      -2.776  -0.615   2.957  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.839   0.663   0.864  0.00  0.00           O+0
HETATM   13  H   UNK     0       1.554  -0.763  -1.724  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.663  -0.818  -0.201  0.00  0.00           H+0
HETATM   15  H   UNK     0       1.341  -2.307  -0.885  0.00  0.00           H+0
HETATM   16  H   UNK     0       3.002   0.077   0.111  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.640  -1.370  -0.639  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.706  -2.778   1.195  0.00  0.00           H+0
HETATM   19  H   UNK     0       4.639  -0.572   2.083  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.393  -2.128   2.909  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.045  -2.082   1.272  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.313   2.812   1.997  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.222   1.470   0.861  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.649   1.888   3.315  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.114   0.847   0.451  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.373  -1.366   2.273  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.096  -0.469   3.800  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.745  -0.952   3.333  0.00  0.00           H+0
CONECT    1    2   13   14   15                                             
CONECT    2    3    1   16   17                                             
CONECT    3    5    2    4   18                                             
CONECT    4    3   19   20   21                                             
CONECT    5    6    3                                                       
CONECT    6    5    7                                                       
CONECT    7    8    6   22   23                                             
CONECT    8    9    7   24                                                  
CONECT    9    8   10   25                                                  
CONECT   10   11    9   12                                                  
CONECT   11   10   26   27   28                                             
CONECT   12   10                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    2                                                            
CONECT   17    2                                                            
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    4                                                            
CONECT   21    4                                                            
CONECT   22    7                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26   11                                                            
CONECT   27   11                                                            
CONECT   28   11                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-{[(2E)-3-[(S)-methanesulphinyl]prop-2-en-1-yl]disulphanyl}butane	Generator

Chemical Formula

C₈H₁₆OS₃

Average Mass

224.4000 Da

Monoisotopic Mass

224.03633 Da

IUPAC Name

(2R)-2-{[(2E)-3-[(S)-methanesulfinyl]prop-2-en-1-yl]disulfanyl}butane

Traditional Name

(2R)-2-{[(2E)-3-[(S)-methanesulfinyl]prop-2-en-1-yl]disulfanyl}butane

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C([H])([H])SS[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])[S@@](=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C8H16OS3/c1-4-8(2)11-10-6-5-7-12(3)9/h5,7-8H,4,6H2,1-3H3/b7-5+/t8-,12+/m1/s1

InChI Key

MRLXFQWCSNFUCF-RZXMPWAMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ferula assa-foetida	Plant	KNApSAcK
Ferula foetida	JEOL database	Duan, H., et al, J. Nat. Prod. 65, 1667 (2002)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfoxides

Sub Class

Not Available

Direct Parent

Sulfoxides

Alternative Parents

Substituents

Dialkyldisulfide
Sulfoxide
Organic disulfide
Sulfenyl compound
Sulfinyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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
logP	3.06	ALOGPS
logP	1.52	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	64.37 m³·mol⁻¹	ChemAxon
Polarizability	23.83 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

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

7848565

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9574107

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Duan, H., et al. (2002). Duan, H., et al, J. Nat. Prod. 65, 1667 (2002). J. Nat. Prod..

Showing NP-Card for Foetisulfide A (NP0026084)

MOL for NP0026084 (Foetisulfide A)

3D MOL for NP0026084 (Foetisulfide A)

3D SDF for NP0026084 (Foetisulfide A)

3D-SDF for NP0026084 (Foetisulfide A)

PDB for NP0026084 (Foetisulfide A)

3D PDB for NP0026084 (Foetisulfide A)

SMILES for NP0026084 (Foetisulfide A)

INCHI for NP0026084 (Foetisulfide A)

Structure for NP0026084 (Foetisulfide A)

3D Structure for NP0026084 (Foetisulfide A)