NP-MRD: Showing NP-Card for sulfoxide (NP0215324)

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Record Information

Version

2.0

Created at

2022-09-05 14:54:44 UTC

Updated at

2022-09-05 14:54:44 UTC

NP-MRD ID

NP0215324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sulfoxide

Description

5-[2-(Octane-1-sulfinyl)propyl]-2H-1,3-benzodioxole belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. sulfoxide is found in Petasites japonicus. 5-[2-(Octane-1-sulfinyl)propyl]-2H-1,3-benzodioxole is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 51  0  0  0  0  0  0  0  0999 V2000
   -6.4849    0.5697   -1.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652    0.2712   -2.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082    0.1274   -1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4790   -0.9957   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437   -1.1261    0.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057   -1.4304    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -1.6052    1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8726   -0.3622    2.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4228    1.0268    1.1677 S   0  0  0  0  0  4  0  0  0  0  0  0
   -1.5365    1.6041    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0957    0.8950    0.2703 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2953    2.1913   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2677    0.6153    1.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5400    0.5008    0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3399    1.6027    0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5459    1.5106   -0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9957    0.2968   -0.9140 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083   -0.8110   -0.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9942   -0.7089   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8809   -1.8797   -1.2751 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2114   -1.4891   -1.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1550   -0.0590   -1.6156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9529   -0.3956   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1472    1.0834   -2.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2749    1.2035   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2614   -0.6448   -2.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    1.1144   -2.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658    1.0809   -0.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1494   -0.0059   -1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5709   -1.9257   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4620   -0.7706    0.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4444   -0.1477    1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017   -1.9546    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7642   -0.5792   -0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214   -2.3725   -0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2627   -2.4326    2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992   -1.8627    0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364   -0.1086    2.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1528   -0.5050    2.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0082    0.0335   -0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9199    2.0594   -1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7160    2.9547    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3250    2.6131   -0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2749    1.4002    1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0526   -0.3475    1.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538    2.5775    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1576    2.3855   -0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3988   -1.5825    0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8626   -1.7968   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5504   -1.8180   -2.5525 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9  8  1  6
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 19  2  0
 19 18  1  0
 18 17  2  0
 17 22  1  0
 22 21  1  0
 21 20  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 20 18  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 16 47  1  0
 15 46  1  0
M  END


  Mrv1572004221603062D          

 22 23  0  0  0  0            999 V2000
   -7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  8  1  0  0  0  0
 15  2  1  0  0  0  0
 15 12  1  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 10  1  0  0  0  0
 18 13  1  0  0  0  0
 18 17  2  0  0  0  0
 20 14  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
 21 18  1  0  0  0  0
 22 11  1  0  0  0  0
 22 15  1  0  0  0  0
 22 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0215324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCS(=O)C(C)CC1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O3S/c1-3-4-5-6-7-8-11-22(19)15(2)12-16-9-10-17-18(13-16)21-14-20-17/h9-10,13,15H,3-8,11-12,14H2,1-2H3

> <INCHI_KEY>
ATTZFSUZZUNHBP-UHFFFAOYSA-N

> <FORMULA>
C18H28O3S

> <MOLECULAR_WEIGHT>
324.48

> <EXACT_MASS>
324.175915936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.47802294647749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[2-(octane-1-sulfinyl)propyl]-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
4.203818495000001

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.74120252621313

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
92.47290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfoxide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.132  -0.476   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.132   2.016   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0      -4.001   2.310   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2   15                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   11                                                       
CONECT    9   10   16                                                       
CONECT   10    9   17                                                       
CONECT   11    8   22                                                       
CONECT   12   15   16                                                       
CONECT   13   16   18                                                       
CONECT   14   20   21                                                       
CONECT   15    2   12   22                                                  
CONECT   16    9   12   13                                                  
CONECT   17   10   18   20                                                  
CONECT   18   13   17   21                                                  
CONECT   19   22                                                            
CONECT   20   14   17                                                       
CONECT   21   14   18                                                       
CONECT   22   11   15   19                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
5-[2-(Octane-1-sulphinyl)propyl]-2H-1,3-benzodioxole	Generator
1,2-(Methylenedioxy)-4-(2-(octylsulfinyl)propyl)benzene	MeSH
Sulfoxide, (r,r)-isomer	MeSH
Sulfoxide, (r,s)-isomer	MeSH

Chemical Formula

C₁₈H₂₈O₃S

Average Mass

324.4800 Da

Monoisotopic Mass

324.17592 Da

IUPAC Name

5-[2-(octane-1-sulfinyl)propyl]-2H-1,3-benzodioxole

Traditional Name

sulfoxide

CAS Registry Number

Not Available

SMILES

CCCCCCCCS(=O)C(C)CC1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C18H28O3S/c1-3-4-5-6-7-8-11-22(19)15(2)12-16-9-10-17-18(13-16)21-14-20-17/h9-10,13,15H,3-8,11-12,14H2,1-2H3

InChI Key

ATTZFSUZZUNHBP-UHFFFAOYSA-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
Petasites japonicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Benzenoid
Sulfoxide
Oxacycle
Sulfinyl compound
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:82267 )
Synergists (C19147 )

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	4.39	ALOGPS
logP	4.2	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	92.47 m³·mol⁻¹	ChemAxon
Polarizability	37.48 Å³	ChemAxon
Number of Rings	2	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

C00049313

Chemspider ID

Not Available

KEGG Compound ID

C19147

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8442

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for sulfoxide (NP0215324)

MOL for NP0215324 (sulfoxide)

3D MOL for NP0215324 (sulfoxide)

3D SDF for NP0215324 (sulfoxide)

3D-SDF for NP0215324 (sulfoxide)

PDB for NP0215324 (sulfoxide)

3D PDB for NP0215324 (sulfoxide)

SMILES for NP0215324 (sulfoxide)

INCHI for NP0215324 (sulfoxide)

Structure for NP0215324 (sulfoxide)

3D Structure for NP0215324 (sulfoxide)