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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:56:30 UTC

Update Date

2021-11-15 21:04:32 UTC

HMDB ID

HMDB0302328

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isothiocyanates

Description

Isothiocyanates is the chemical group -N=C=S, formed by substituting the oxygen in the isocyanate group with a sulfur. Many natural isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates. These natural isothiocyanates, such as allyl isothiocyanate, are also known as mustard oils. An artificial isothiocyanate, phenyl isothiocyanate, is used for amino acid sequencing in the Edman degradation . Isothiocyanates is a member of the class of compounds known as sulfonated stilbenes. Sulfonated stilbenes are stilbenes that carry a sulfone group at one or more positions of either benzene rings. Isothiocyanates is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). Isothiocyanates can be found in horseradish, which makes isothiocyanates a potential biomarker for the consumption of this food product.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241221232D          

 30 29  0  0  0  0            999 V2000
    0.3572    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    3.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    4.3313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.0313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    0.3168    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -3.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -3.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -4.3312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1987   -1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737   -0.3168    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.7399    0.0000    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.9812    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
 14  3  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  2  0  0  0  0
 17 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
M  CHG  4  13  -1  28  -1  29   1  30   1
M  END

HMDB0302328
     RDKit          3D
Isothiocyanates
 38 37  0  0  0  0  0  0  0  0999 V2000
   -3.8625    3.0796    0.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528    2.3483    0.1500 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.6803    2.9177    1.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873    2.5635   -1.3926 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.8531    0.6396    0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1407    0.2145    0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4642   -1.1076    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8196   -1.5260    1.1065 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7755   -0.9034    0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0190   -0.6153   -0.4767 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364   -2.0159    0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -1.6134    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8297   -0.2913    0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    0.1883    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914   -0.5594    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961    0.0005   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1973    1.3202   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4843    1.7794   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    0.8633   -0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8206    1.3139   -1.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4309    2.1667   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0779    3.5467    0.2479 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2643   -0.4739   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -0.8861   -0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -2.5738   -0.0834 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.7131   -3.1457   -1.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -3.3107   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -2.7459    1.4704 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -4.9729    0.9288    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282   -3.0741    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -2.3518    0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309    1.2720   -0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4472   -1.6205    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974    2.0542   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    2.8154   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0868   -1.1976   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  7 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  2  0
 19 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  2  0
 25 28  1  0
 13  5  1  0
 24 16  1  0
  6 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 23 38  1  0
M  CHG  4   4  -1  28  -1  29   1  30   1
M  END


  Mrv0541 02241221232D          

 30 29  0  0  0  0            999 V2000
    0.3572    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    3.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    4.3313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.0313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1987    1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    0.3168    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -3.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -3.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -4.3312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1987   -1.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737   -0.3168    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.7399    0.0000    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.9812    0.0000 Na  0  3  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
 14  3  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  2  0  0  0  0
 17 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
M  CHG  4  13  -1  28  -1  29   1  30   1
M  END
> <DATABASE_ID>
HMDB0302328

> <DATABASE_NAME>
hmdb

> <SMILES>
[Na+].[Na+].[O-]S(=O)(=O)C1=C(C=CC2=C(C=C(C=C2)N=C=S)S([O-])(=O)=O)C=CC(=C1)N=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C16H10N2O6S4.2Na/c19-27(20,21)15-7-13(17-9-25)5-3-11(15)1-2-12-4-6-14(18-10-26)8-16(12)28(22,23)24;;/h1-8H,(H,19,20,21)(H,22,23,24);;/q;2*+1/p-2

> <INCHI_KEY>
GEPAYBXVXXBSKP-UHFFFAOYSA-L

> <FORMULA>
C16H8N2Na2O6S4

> <MOLECULAR_WEIGHT>
498.484

> <EXACT_MASS>
497.906058108

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
42.44005109873838

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
disodium 5-isothiocyanato-2-[2-(4-isothiocyanato-2-sulfonatophenyl)ethenyl]benzene-1-sulfonate

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
4.328948327071101

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-2.468181842810856

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.206516694672181

> <JCHEM_PKA_STRONGEST_BASIC>
0.23208373444837882

> <JCHEM_POLAR_SURFACE_AREA>
139.12

> <JCHEM_REFRACTIVITY>
114.6402

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
disodium 5-isothiocyanato-2-[2-(4-isothiocyanato-2-sulfonatophenyl)ethenyl]benzenesulfonate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302328
     RDKit          3D
Isothiocyanates
 38 37  0  0  0  0  0  0  0  0999 V2000
   -3.8625    3.0796    0.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528    2.3483    0.1500 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.6803    2.9177    1.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873    2.5635   -1.3926 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.8531    0.6396    0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1407    0.2145    0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4642   -1.1076    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8196   -1.5260    1.1065 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7755   -0.9034    0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0190   -0.6153   -0.4767 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364   -2.0159    0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -1.6134    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8297   -0.2913    0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    0.1883    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914   -0.5594    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961    0.0005   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1973    1.3202   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4843    1.7794   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    0.8633   -0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8206    1.3139   -1.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4309    2.1667   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0779    3.5467    0.2479 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2643   -0.4739   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -0.8861   -0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -2.5738   -0.0834 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.7131   -3.1457   -1.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -3.3107   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -2.7459    1.4704 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -4.9729    0.9288    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282   -3.0741    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -2.3518    0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309    1.2720   -0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4472   -1.6205    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974    2.0542   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    2.8154   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0868   -1.1976   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  7 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  2  0
 19 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  2  0
 25 28  1  0
 13  5  1  0
 24 16  1  0
  6 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 23 38  1  0
M  CHG  4   4  -1  28  -1  29   1  30   1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.667   4.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667   2.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667   1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001   2.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001   4.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667   5.005   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.667   6.545   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.667   7.315   0.000  0.00  0.00           C+0
HETATM    9  S   UNK     0       2.001   8.085   0.000  0.00  0.00           S+0
HETATM   10  S   UNK     0      -3.334   1.925   0.000  0.00  0.00           S+0
HETATM   11  O   UNK     0      -4.104   3.259   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.668   1.155   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.564   0.591   0.000  0.00  0.00           O-1
HETATM   14  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.667  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.001  -2.695   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.001  -4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.667  -5.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.667  -4.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.667  -2.695   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       0.667  -6.545   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -0.667  -7.315   0.000  0.00  0.00           C+0
HETATM   24  S   UNK     0      -2.001  -8.085   0.000  0.00  0.00           S+0
HETATM   25  S   UNK     0       3.334  -1.925   0.000  0.00  0.00           S+0
HETATM   26  O   UNK     0       4.104  -3.259   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.668  -1.155   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.564  -0.591   0.000  0.00  0.00           O-1
HETATM   29 Na   UNK     0       8.848   0.000   0.000  0.00  0.00          Na+1
HETATM   30 Na   UNK     0       0.000 -11.165   0.000  0.00  0.00          Na+1
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    4   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   17   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

COMPND    HMDB0302328
HETATM    1  O1  UNL     1      -3.862   3.080   0.153  1.00  0.00           O  
HETATM    2  S1  UNL     1      -2.553   2.348   0.150  1.00  0.00           S  
HETATM    3  O2  UNL     1      -1.680   2.918   1.215  1.00  0.00           O  
HETATM    4  O3  UNL     1      -1.887   2.563  -1.393  1.00  0.00           O1-
HETATM    5  C1  UNL     1      -2.853   0.640   0.396  1.00  0.00           C  
HETATM    6  C2  UNL     1      -4.141   0.215   0.644  1.00  0.00           C  
HETATM    7  C3  UNL     1      -4.464  -1.108   0.849  1.00  0.00           C  
HETATM    8  N1  UNL     1      -5.820  -1.526   1.106  1.00  0.00           N  
HETATM    9  C4  UNL     1      -6.776  -0.903   0.535  1.00  0.00           C  
HETATM   10  S2  UNL     1      -8.019  -0.615  -0.477  1.00  0.00           S  
HETATM   11  C5  UNL     1      -3.436  -2.016   0.797  1.00  0.00           C  
HETATM   12  C6  UNL     1      -2.119  -1.613   0.547  1.00  0.00           C  
HETATM   13  C7  UNL     1      -1.830  -0.291   0.348  1.00  0.00           C  
HETATM   14  C8  UNL     1      -0.479   0.188   0.084  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.591  -0.559   0.006  1.00  0.00           C  
HETATM   16  C10 UNL     1       1.896   0.000  -0.260  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.197   1.320  -0.460  1.00  0.00           C  
HETATM   18  C12 UNL     1       3.484   1.779  -0.712  1.00  0.00           C  
HETATM   19  C13 UNL     1       4.499   0.863  -0.761  1.00  0.00           C  
HETATM   20  N2  UNL     1       5.821   1.314  -1.017  1.00  0.00           N  
HETATM   21  C14 UNL     1       6.431   2.167  -0.316  1.00  0.00           C  
HETATM   22  S3  UNL     1       7.078   3.547   0.248  1.00  0.00           S  
HETATM   23  C15 UNL     1       4.264  -0.474  -0.569  1.00  0.00           C  
HETATM   24  C16 UNL     1       2.977  -0.886  -0.323  1.00  0.00           C  
HETATM   25  S4  UNL     1       2.683  -2.574  -0.083  1.00  0.00           S  
HETATM   26  O4  UNL     1       1.713  -3.146  -1.073  1.00  0.00           O  
HETATM   27  O5  UNL     1       3.973  -3.311  -0.057  1.00  0.00           O  
HETATM   28  O6  UNL     1       2.012  -2.746   1.470  1.00  0.00           O1-
HETATM   29 NA1  UNL     1       0.000   0.000   0.000  1.00  0.00          NA1+
HETATM   30 NA2  UNL     1       0.000   0.000   0.000  1.00  0.00          NA1+
HETATM   31  H1  UNL     1      -4.973   0.929   0.688  1.00  0.00           H  
HETATM   32  H2  UNL     1      -3.628  -3.074   0.951  1.00  0.00           H  
HETATM   33  H3  UNL     1      -1.342  -2.352   0.514  1.00  0.00           H  
HETATM   34  H4  UNL     1      -0.331   1.272  -0.066  1.00  0.00           H  
HETATM   35  H5  UNL     1       0.447  -1.621   0.153  1.00  0.00           H  
HETATM   36  H6  UNL     1       1.397   2.054  -0.423  1.00  0.00           H  
HETATM   37  H7  UNL     1       3.643   2.815  -0.857  1.00  0.00           H  
HETATM   38  H8  UNL     1       5.087  -1.198  -0.611  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    5    6    6   13
CONECT    6    7   31
CONECT    7    8   11   11
CONECT    8    9    9
CONECT    9   10   10
CONECT   11   12   32
CONECT   12   13   13   33
CONECT   13   14
CONECT   14   15   15   34
CONECT   15   16   35
CONECT   16   17   17   24
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   23
CONECT   20   21   21
CONECT   21   22   22
CONECT   23   24   24   38
CONECT   24   25
CONECT   25   26   26   27   27
CONECT   25   28
END

HMDB0302328
     RDKit          3D
Isothiocyanates
 38 37  0  0  0  0  0  0  0  0999 V2000
   -3.8625    3.0796    0.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528    2.3483    0.1500 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.6803    2.9177    1.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873    2.5635   -1.3926 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.8531    0.6396    0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1407    0.2145    0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4642   -1.1076    0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8196   -1.5260    1.1065 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7755   -0.9034    0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0190   -0.6153   -0.4767 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364   -2.0159    0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -1.6134    0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8297   -0.2913    0.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    0.1883    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914   -0.5594    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961    0.0005   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1973    1.3202   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4843    1.7794   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    0.8633   -0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8206    1.3139   -1.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4309    2.1667   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0779    3.5467    0.2479 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2643   -0.4739   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -0.8861   -0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -2.5738   -0.0834 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.7131   -3.1457   -1.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -3.3107   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -2.7459    1.4704 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -4.9729    0.9288    0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282   -3.0741    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -2.3518    0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309    1.2720   -0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4472   -1.6205    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974    2.0542   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    2.8154   -0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0868   -1.1976   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
  7 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  2  0
 19 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  2  0
 25 28  1  0
 13  5  1  0
 24 16  1  0
  6 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 23 38  1  0
M  CHG  4   4  -1  28  -1  29   1  30   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₈N₂Na₂O₆S₄

Average Molecular Weight

498.484

Monoisotopic Molecular Weight

497.906058108

IUPAC Name

disodium 5-isothiocyanato-2-[2-(4-isothiocyanato-2-sulfonatophenyl)ethenyl]benzene-1-sulfonate

Traditional Name

disodium 5-isothiocyanato-2-[2-(4-isothiocyanato-2-sulfonatophenyl)ethenyl]benzenesulfonate

CAS Registry Number

Not Available

SMILES

[Na+].[Na+].[O-]S(=O)(=O)C1=C(C=CC2=C(C=C(C=C2)N=C=S)S([O-])(=O)=O)C=CC(=C1)N=C=S

InChI Identifier

InChI=1S/C16H10N2O6S4.2Na/c19-27(20,21)15-7-13(17-9-25)5-3-11(15)1-2-12-4-6-14(18-10-26)8-16(12)28(22,23)24;;/h1-8H,(H,19,20,21)(H,22,23,24);;/q;2*+1/p-2

InChI Key

GEPAYBXVXXBSKP-UHFFFAOYSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfonated stilbenes. These are stilbenes that carry a sulfone group at one or more positions of either benzene rings.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Sulfonated stilbenes

Direct Parent

Sulfonated stilbenes

Alternative Parents

Substituents

Sulfonated stilbene
Benzenesulfonate
Arylsulfonic acid or derivatives
1-sulfo,2-unsubstituted aromatic compound
Benzenesulfonyl group
Styrene
Monocyclic benzene moiety
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Isothiocyanate
Organic alkali metal salt
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organosulfur compound
Organonitrogen compound
Organic salt
Organic sodium salt
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Horseradish (FooDB: FOOD00018)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3	ALOGPS
logP	4.33	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	-3.2	ChemAxon
pKa (Strongest Basic)	0.23	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	139.12 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.64 m³·mol⁻¹	ChemAxon
Polarizability	42.44 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	220.735	32859911
AllCCS	[M+H-H2O]+	218.78	32859911
AllCCS	[M+Na]+	223.027	32859911
AllCCS	[M+NH4]+	222.519	32859911
AllCCS	[M-H]-	186.856	32859911
AllCCS	[M+Na-2H]-	187.358	32859911
AllCCS	[M+HCOO]-	188.053	32859911
DeepCCS	[M+H]+	190.743	30932474
DeepCCS	[M-H]-	188.348	30932474
DeepCCS	[M-2H]-	221.595	30932474
DeepCCS	[M+Na]+	196.684	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isothiocyanates 10V, Positive-QTOF	splash10-0002-0000900000-17b9bb9b0a12f77cbf76	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isothiocyanates 20V, Positive-QTOF	splash10-0005-0017900000-a07ccb1110c9a11daa9d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isothiocyanates 40V, Positive-QTOF	splash10-0a4i-5795000000-f4eeefc4ab552cb1720e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isothiocyanates 10V, Negative-QTOF	splash10-0002-0000900000-6c3d1ffc6a3da973b739	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isothiocyanates 20V, Negative-QTOF	splash10-0002-0000900000-6c3d1ffc6a3da973b739	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isothiocyanates 40V, Negative-QTOF	splash10-0002-0000900000-6c3d1ffc6a3da973b739	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004147

KNApSAcK ID

Not Available

Chemspider ID

3500906

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

186794

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Isothiocyanates (HMDB0302328)

MOL for HMDB0302328 (Isothiocyanates)

3D MOL for HMDB0302328 (Isothiocyanates)

3D SDF for HMDB0302328 (Isothiocyanates)

3D-SDF for HMDB0302328 (Isothiocyanates)

PDB for HMDB0302328 (Isothiocyanates)

3D PDB for HMDB0302328 (Isothiocyanates)

SMILES for HMDB0302328 (Isothiocyanates)

INCHI for HMDB0302328 (Isothiocyanates)

Structure for HMDB0302328 (Isothiocyanates)

3D Structure for HMDB0302328 (Isothiocyanates)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra