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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:09:32 UTC

Update Date

2021-09-26 22:56:38 UTC

HMDB ID

HMDB0247146

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate

Description

2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Based on a literature review very few articles have been published on 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3,4-tri-o-acetylarabinopyranosyl isothiocyanate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247146
     RDKit          3D
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.0752   -1.5746   -1.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.5261   -0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314    0.5749   -0.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0103   -0.7292   -0.1247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    0.3283    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410   -0.1637    1.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590   -1.4359    1.7661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -1.2299    1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632   -0.6922    2.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -1.4759    3.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -1.9737    5.0446 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421   -0.3675    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -1.2087   -0.9157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608   -1.2789   -1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -2.1856   -2.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990   -0.5219   -1.1839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    0.6423   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3802    1.9125    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5071    3.0331   -0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    4.3552    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    2.8830   -1.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475   -1.2270   -2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757   -2.5364   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -1.5760   -0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9830    1.2261    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325   -0.2528    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614    0.5179    2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041   -2.2436    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    0.1838    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -2.4757   -2.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -1.7289   -3.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0664   -3.1416   -2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556    0.7820   -1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452    4.4867    1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987    4.4674    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455    5.1525   -0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
M  END


  Mrv1652309112102092D          

 21 21  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    0.0000    0.0000    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
   -0.7145    1.2375    0.0000 O   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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247146

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO7S/c1-6(14)18-9-4-17-12(13-5-21)11(20-8(3)16)10(9)19-7(2)15/h9-12H,4H2,1-3H3

> <INCHI_KEY>
RCHZRAFPHKCWRI-UHFFFAOYSA-N

> <FORMULA>
C12H15NO7S

> <MOLECULAR_WEIGHT>
317.31

> <EXACT_MASS>
317.056923001

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.048036451582107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
0.6093990776666662

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.064768633053593

> <JCHEM_PKA_STRONGEST_BASIC>
-4.331819781187818

> <JCHEM_POLAR_SURFACE_AREA>
100.49

> <JCHEM_REFRACTIVITY>
70.48320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247146
     RDKit          3D
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.0752   -1.5746   -1.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.5261   -0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314    0.5749   -0.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0103   -0.7292   -0.1247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    0.3283    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410   -0.1637    1.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590   -1.4359    1.7661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -1.2299    1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632   -0.6922    2.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -1.4759    3.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -1.9737    5.0446 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421   -0.3675    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -1.2087   -0.9157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608   -1.2789   -1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -2.1856   -2.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990   -0.5219   -1.1839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    0.6423   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3802    1.9125    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5071    3.0331   -0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    4.3552    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    2.8830   -1.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475   -1.2270   -2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757   -2.5364   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -1.5760   -0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9830    1.2261    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325   -0.2528    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614    0.5179    2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041   -2.2436    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    0.1838    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -2.4757   -2.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -1.7289   -3.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0664   -3.1416   -2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556    0.7820   -1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452    4.4867    1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987    4.4674    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455    5.1525   -0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  S   UNK     0       4.001  -3.850   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0247146
HETATM    1  C1  UNL     1      -4.075  -1.575  -1.309  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.295  -0.526  -0.581  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.831   0.575  -0.381  1.00  0.00           O  
HETATM    4  O2  UNL     1      -2.010  -0.729  -0.125  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.347   0.328   0.558  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.041  -0.164   1.965  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.459  -1.436   1.766  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.838  -1.230   1.395  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.563  -0.692   2.546  1.00  0.00           N  
HETATM   10  C6  UNL     1       1.915  -1.476   3.508  1.00  0.00           C  
HETATM   11  S1  UNL     1       1.713  -1.974   5.045  1.00  0.00           S  
HETATM   12  C7  UNL     1       1.042  -0.368   0.200  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.279  -1.209  -0.916  1.00  0.00           O  
HETATM   14  C8  UNL     1       2.461  -1.279  -1.601  1.00  0.00           C  
HETATM   15  C9  UNL     1       2.610  -2.186  -2.750  1.00  0.00           C  
HETATM   16  O5  UNL     1       3.399  -0.522  -1.184  1.00  0.00           O  
HETATM   17  C10 UNL     1      -0.001   0.642  -0.073  1.00  0.00           C  
HETATM   18  O6  UNL     1       0.380   1.913   0.429  1.00  0.00           O  
HETATM   19  C11 UNL     1       0.507   3.033  -0.363  1.00  0.00           C  
HETATM   20  C12 UNL     1       0.906   4.355   0.169  1.00  0.00           C  
HETATM   21  O7  UNL     1       0.261   2.883  -1.605  1.00  0.00           O  
HETATM   22  H1  UNL     1      -4.148  -1.227  -2.357  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.576  -2.536  -1.185  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.091  -1.576  -0.840  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.983   1.226   0.638  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.933  -0.253   2.591  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.261   0.518   2.408  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.304  -2.244   1.222  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.017   0.184   0.355  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.684  -2.476  -2.933  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.271  -1.729  -3.712  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.066  -3.142  -2.601  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.156   0.782  -1.174  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.445   4.487   1.173  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.999   4.467   0.249  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.546   5.153  -0.527  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   17   25
CONECT    6    7   26   27
CONECT    7    8
CONECT    8    9   12   28
CONECT    9   10   10
CONECT   10   11   11
CONECT   12   13   17   29
CONECT   13   14
CONECT   14   15   16   16
CONECT   15   30   31   32
CONECT   17   18   33
CONECT   18   19
CONECT   19   20   21   21
CONECT   20   34   35   36
END

HMDB0247146
     RDKit          3D
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.0752   -1.5746   -1.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.5261   -0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8314    0.5749   -0.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0103   -0.7292   -0.1247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466    0.3283    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410   -0.1637    1.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590   -1.4359    1.7661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -1.2299    1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632   -0.6922    2.5463 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154   -1.4759    3.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -1.9737    5.0446 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421   -0.3675    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -1.2087   -0.9157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608   -1.2789   -1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -2.1856   -2.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990   -0.5219   -1.1839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    0.6423   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3802    1.9125    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5071    3.0331   -0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    4.3552    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2612    2.8830   -1.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475   -1.2270   -2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5757   -2.5364   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -1.5760   -0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9830    1.2261    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325   -0.2528    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614    0.5179    2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041   -2.2436    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    0.1838    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6837   -2.4757   -2.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -1.7289   -3.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0664   -3.1416   -2.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556    0.7820   -1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452    4.4867    1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987    4.4674    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455    5.1525   -0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanic acid	Generator

Chemical Formula

C₁₂H₁₅NO₇S

Average Molecular Weight

317.31

Monoisotopic Molecular Weight

317.056923001

IUPAC Name

4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate

Traditional Name

4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O

InChI Identifier

InChI=1S/C12H15NO7S/c1-6(14)18-9-4-17-12(13-5-21)11(20-8(3)16)10(9)19-7(2)15/h9-12H,4H2,1-3H3

InChI Key

RCHZRAFPHKCWRI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
Tricarboxylic acid or derivatives
Oxane
Isothiocyanate
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	1.45	ALOGPS
logP	0.61	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	15.06	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	100.49 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	70.48 m³·mol⁻¹	ChemAxon
Polarizability	30.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	161.683	30932474
DeepCCS	[M-H]-	159.325	30932474
DeepCCS	[M-2H]-	192.386	30932474
DeepCCS	[M+Na]+	167.776	30932474
AllCCS	[M+H]+	169.1	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.7	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	169.1	32859911
AllCCS	[M+HCOO]-	169.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate	CC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O	3445.9	Standard polar	33892256
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate	CC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O	1993.7	Standard non polar	33892256
2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate	CC(=O)OC1COC(N=C=S)C(OC(C)=O)C1OC(C)=O	1935.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aov-5490000000-0bafe2592a3b4e5da337	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 10V, Positive-QTOF	splash10-014i-0039000000-3bdb586ad93b540b6eee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 20V, Positive-QTOF	splash10-014i-0249000000-005a7499e3243c6042b6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 40V, Positive-QTOF	splash10-01p2-9430000000-0308d5a43e28d50ae1bb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 10V, Negative-QTOF	splash10-014i-0096000000-7fb9810901657122e734	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 20V, Negative-QTOF	splash10-0a4i-9341000000-0680aa31397330427ce2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate 40V, Negative-QTOF	splash10-0bu0-9180000000-63e8646a348670246d02	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3108815

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3884507

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate (HMDB0247146)

MOL for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

3D MOL for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

3D SDF for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

3D-SDF for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

PDB for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

3D PDB for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

SMILES for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

INCHI for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

Structure for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

3D Structure for HMDB0247146 (2,3,4-Tri-O-acetylarabinopyranosyl isothiocyanate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra