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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:55 UTC

Update Date

2022-03-07 02:53:28 UTC

HMDB ID

HMDB0032802

Secondary Accession Numbers

HMDB32802

Metabolite Identification

Common Name

4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate

Description

4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate, also known as 4-hydroxybenzyl isothiocyanate 4"-acetylrhamnoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate.

Structure

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

HMDB0032802
     RDKit          3D
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate
 43 44  0  0  0  0  0  0  0  0999 V2000
    6.7341   -0.5628    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -0.1465   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2609    0.5674   -1.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2131   -0.5229    0.5023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9350   -0.1495    0.0890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0077   -1.3237   -0.1435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7997   -1.6057   -1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149   -1.1886    0.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    0.0204    0.2988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9758    0.0403    1.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658    0.2086    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180    0.1814    1.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5536    0.3489    1.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9599    0.5423    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4136    0.7224   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0616   -0.5406   -0.3950 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4048   -1.5997   -0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8188   -3.0970   -0.1679 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242    0.5685   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.4015   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0196    1.2061    0.7215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3005    2.0570   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    0.6888    1.2258 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2569    1.7233    1.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2195    0.2547    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7008   -1.5183    0.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3628   -0.6522   -0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9007    0.4771   -0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5255   -2.2191    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955   -2.6647   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668   -1.3817   -1.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982   -0.9911   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662    0.1688   -0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.0280    2.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2534    0.3204    2.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5080    1.3587   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8647    1.2563    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3064    0.7188   -1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    0.4262   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5280    1.8313    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039    1.6236   -1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220    0.0738    2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234    2.3493    0.6981 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  2  0
 14 19  1  0
 19 20  2  0
  9 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23  5  1  0
 20 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  6
  6 29  1  1
  7 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  6
 12 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  1
 22 41  1  0
 23 42  1  1
 24 43  1  0
M  END


  Mrv1652309272007322D          

 24 25  0  0  0  0            999 V2000
10013.546210014.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10016.404110016.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.119310015.7499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10012.120410013.6888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.690110014.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10012.120410016.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.690110016.1623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.690310015.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.975910016.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.261310015.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.261310014.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.975710014.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.690310014.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.118910016.1631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.404410015.7505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.404410014.9256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.118910014.5131    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.833410014.9256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.833410015.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.975410015.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.260310016.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.976010014.9234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10017.944810015.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.770410015.7508    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  1 11  1  0  0  0  0
  8  2  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 18 19  1  0  0  0  0
 18  1  1  1  0  0  0
 17  4  1  6  0  0  0
 16  5  1  6  0  0  0
 15  7  1  1  0  0  0
 14  6  1  6  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  2  3  1  0  0  0  0
  3 23  2  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032802

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO6S/c1-9-15(22-10(2)18)13(19)14(20)16(21-9)23-12-5-3-11(4-6-12)7-17-8-24/h3-6,9,13-16,19-20H,7H2,1-2H3/t9-,13-,14+,15-,16-/m0/s1

> <INCHI_KEY>
WVUZLAMBBZISKM-QOYUQHOESA-N

> <FORMULA>
C16H19NO6S

> <MOLECULAR_WEIGHT>
353.39

> <EXACT_MASS>
353.09330851

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.956257166162885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[4-(isothiocyanatomethyl)phenoxy]-2-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.7105251333333338

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.879548787668497

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.260449612559063

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6916081753265226

> <JCHEM_POLAR_SURFACE_AREA>
97.58000000000001

> <JCHEM_REFRACTIVITY>
87.6748

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[4-(isothiocyanatomethyl)phenoxy]-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032802
     RDKit          3D
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate
 43 44  0  0  0  0  0  0  0  0999 V2000
    6.7341   -0.5628    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -0.1465   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2609    0.5674   -1.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2131   -0.5229    0.5023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9350   -0.1495    0.0890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0077   -1.3237   -0.1435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7997   -1.6057   -1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149   -1.1886    0.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    0.0204    0.2988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9758    0.0403    1.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658    0.2086    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180    0.1814    1.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5536    0.3489    1.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9599    0.5423    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4136    0.7224   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0616   -0.5406   -0.3950 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4048   -1.5997   -0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8188   -3.0970   -0.1679 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242    0.5685   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.4015   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0196    1.2061    0.7215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3005    2.0570   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    0.6888    1.2258 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2569    1.7233    1.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2195    0.2547    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7008   -1.5183    0.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3628   -0.6522   -0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9007    0.4771   -0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5255   -2.2191    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955   -2.6647   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668   -1.3817   -1.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982   -0.9911   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662    0.1688   -0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.0280    2.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2534    0.3204    2.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5080    1.3587   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8647    1.2563    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3064    0.7188   -1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    0.4262   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5280    1.8313    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039    1.6236   -1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220    0.0738    2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234    2.3493    0.6981 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  2  0
 14 19  1  0
 19 20  2  0
  9 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23  5  1  0
 20 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  6
  6 29  1  1
  7 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  6
 12 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  1
 22 41  1  0
 23 42  1  1
 24 43  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8691.9538693.758   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8697.2888696.836   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8698.6238696.066   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0    8689.2918692.219   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8686.6228693.758   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8689.2918698.375   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8686.6228696.836   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8695.9558696.068   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8694.6228696.838   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8693.2888696.067   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8693.2888694.528   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8694.6218693.758   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8695.9558694.528   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8689.2898696.838   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8687.9558696.068   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8687.9558694.528   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8689.2898693.758   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8690.6228694.528   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8690.6228696.068   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8685.2878696.064   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8683.9538696.835   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8685.2898694.524   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8700.1648696.067   0.000  0.00  0.00           C+0
HETATM   24  S   UNK     0    8701.7058696.068   0.000  0.00  0.00           S+0
CONECT    1   11   18                                                       
CONECT    2    8    3                                                       
CONECT    3    2   23                                                       
CONECT    4   17                                                            
CONECT    5   16                                                            
CONECT    6   14                                                            
CONECT    7   15   20                                                       
CONECT    8    9   13    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    1                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   15   19    6                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    5                                                  
CONECT   17   16   18    4                                                  
CONECT   18   17   19    1                                                  
CONECT   19   14   18                                                       
CONECT   20    7   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    3   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0032802
HETATM    1  C1  UNL     1       6.734  -0.563   0.316  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.383  -0.147  -0.152  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.261   0.567  -1.166  1.00  0.00           O  
HETATM    4  O2  UNL     1       4.213  -0.523   0.502  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.935  -0.149   0.089  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.008  -1.324  -0.143  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.800  -1.606  -1.605  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.815  -1.189   0.555  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.178   0.020   0.299  1.00  0.00           C  
HETATM   10  O4  UNL     1      -0.976   0.040   1.092  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.266   0.209   0.747  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.218   0.181   1.769  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.554   0.349   1.470  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.960   0.542   0.179  1.00  0.00           C  
HETATM   15  C11 UNL     1      -6.414   0.722  -0.128  1.00  0.00           C  
HETATM   16  N1  UNL     1      -7.062  -0.541  -0.395  1.00  0.00           N  
HETATM   17  C12 UNL     1      -6.405  -1.600  -0.136  1.00  0.00           C  
HETATM   18  S1  UNL     1      -5.819  -3.097  -0.168  1.00  0.00           S  
HETATM   19  C13 UNL     1      -4.024   0.569  -0.820  1.00  0.00           C  
HETATM   20  C14 UNL     1      -2.660   0.401  -0.548  1.00  0.00           C  
HETATM   21  C15 UNL     1       1.020   1.206   0.722  1.00  0.00           C  
HETATM   22  O5  UNL     1       1.300   2.057  -0.362  1.00  0.00           O  
HETATM   23  C16 UNL     1       2.331   0.689   1.226  1.00  0.00           C  
HETATM   24  O6  UNL     1       3.257   1.723   1.446  1.00  0.00           O  
HETATM   25  H1  UNL     1       7.220   0.255   0.901  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.701  -1.518   0.868  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.363  -0.652  -0.618  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.901   0.477  -0.809  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.525  -2.219   0.293  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.995  -2.665  -1.870  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.767  -1.382  -1.940  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.498  -0.991  -2.212  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.066   0.169  -0.751  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.885   0.028   2.784  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.253   0.320   2.292  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.508   1.359  -1.013  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.865   1.256   0.736  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.306   0.719  -1.851  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.940   0.426  -1.355  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.528   1.831   1.493  1.00  0.00           H  
HETATM   41  H17 UNL     1       1.004   1.624  -1.177  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.222   0.074   2.141  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.223   2.349   0.698  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   23   28
CONECT    6    7    8   29
CONECT    7   30   31   32
CONECT    8    9
CONECT    9   10   21   33
CONECT   10   11
CONECT   11   12   12   20
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   19
CONECT   15   16   36   37
CONECT   16   17   17
CONECT   17   18   18
CONECT   19   20   20   38
CONECT   20   39
CONECT   21   22   23   40
CONECT   22   41
CONECT   23   24   42
CONECT   24   43
END

HMDB0032802
     RDKit          3D
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate
 43 44  0  0  0  0  0  0  0  0999 V2000
    6.7341   -0.5628    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -0.1465   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2609    0.5674   -1.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2131   -0.5229    0.5023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9350   -0.1495    0.0890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0077   -1.3237   -0.1435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7997   -1.6057   -1.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8149   -1.1886    0.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    0.0204    0.2988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9758    0.0403    1.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658    0.2086    0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180    0.1814    1.7691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5536    0.3489    1.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9599    0.5423    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4136    0.7224   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0616   -0.5406   -0.3950 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4048   -1.5997   -0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8188   -3.0970   -0.1679 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242    0.5685   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603    0.4015   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0196    1.2061    0.7215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3005    2.0570   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    0.6888    1.2258 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2569    1.7233    1.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2195    0.2547    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7008   -1.5183    0.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3628   -0.6522   -0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9007    0.4771   -0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5255   -2.2191    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955   -2.6647   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668   -1.3817   -1.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982   -0.9911   -2.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662    0.1688   -0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.0280    2.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2534    0.3204    2.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5080    1.3587   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8647    1.2563    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3064    0.7188   -1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    0.4262   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5280    1.8313    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039    1.6236   -1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2220    0.0738    2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234    2.3493    0.6981 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  2  0
 14 19  1  0
 19 20  2  0
  9 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23  5  1  0
 20 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  6
  6 29  1  1
  7 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  6
 12 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  1
 22 41  1  0
 23 42  1  1
 24 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-[(4'-O-Acetyl-a-L-rhamnosyloxy)benzyl]isothiocyanate	Generator
4-[(4'-O-Acetyl-a-L-rhamnosyloxy)benzyl]isothiocyanic acid	Generator
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanic acid	Generator
4-[(4'-O-Acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate	Generator
4-[(4'-O-Acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanic acid	Generator
4-Hydroxybenzyl isothiocyanic acid 4''-acetylrhamnoside	HMDB
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl isothiocyanate	HMDB
4-(4’-O-acetyl-α-L-rhamnosyloxy)benzyl isothiocyanate	HMDB
4-Hydroxybenzyl isothiocyanate 4"-acetylrhamnoside	HMDB
4-Hydroxybenzyl isothiocyanate 4″-acetylrhamnoside	HMDB
4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate	HMDB
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate	HMDB

Chemical Formula

C₁₆H₁₉NO₆S

Average Molecular Weight

353.39

Monoisotopic Molecular Weight

353.09330851

IUPAC Name

(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[4-(isothiocyanatomethyl)phenoxy]-2-methyloxan-3-yl acetate

Traditional Name

(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[4-(isothiocyanatomethyl)phenoxy]-2-methyloxan-3-yl acetate

CAS Registry Number

73255-41-1

SMILES

C[C@@H]1O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C16H19NO6S/c1-9-15(22-10(2)18)13(19)14(20)16(21-9)23-12-5-3-11(4-6-12)7-17-8-24/h3-6,9,13-16,19-20H,7H2,1-2H3/t9-,13-,14+,15-,16-/m0/s1

InChI Key

WVUZLAMBBZISKM-QOYUQHOESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
1,2-diol
Carboxylic acid ester
Isothiocyanate
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organosulfur compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

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
Water Solubility	0.17 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.71	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.67 m³·mol⁻¹	ChemAxon
Polarizability	35.96 Å³	ChemAxon
Number of Rings	2	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]+	177.748	30932474
DeepCCS	[M-H]-	175.353	30932474
DeepCCS	[M-2H]-	208.748	30932474
DeepCCS	[M+Na]+	183.683	30932474
AllCCS	[M+H]+	181.6	32859911
AllCCS	[M+H-H2O]+	178.8	32859911
AllCCS	[M+NH4]+	184.2	32859911
AllCCS	[M+Na]+	184.9	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.8	32859911
AllCCS	[M+HCOO]-	181.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate	C[C@@H]1O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	4406.7	Standard polar	33892256
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate	C[C@@H]1O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	2654.8	Standard non polar	33892256
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate	C[C@@H]1O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	2808.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate,1TMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2548.9	Semi standard non polar	33892256
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate,1TMS,isomer #2	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2555.2	Semi standard non polar	33892256
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate,2TMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2576.9	Semi standard non polar	33892256
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate,1TBDMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2762.2	Semi standard non polar	33892256
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate,1TBDMS,isomer #2	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2766.8	Semi standard non polar	33892256
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate,2TBDMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CN=C=S)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2914.9	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 - 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]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 - 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate 10V, Positive-QTOF	splash10-066r-0902000000-0619f8248f86278d6662	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate 20V, Positive-QTOF	splash10-0aor-1932000000-b1fdbf2d6b6139347c93	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate 40V, Positive-QTOF	splash10-0a4i-2910000000-4c7895efa7ac534c6636	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate 10V, Negative-QTOF	splash10-0a4i-9001000000-e59e28a653873a5d36f7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate 20V, Negative-QTOF	splash10-0a4i-9000000000-33228dc278ccbd4f4c0e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate 40V, Negative-QTOF	splash10-0a4i-9000000000-83249ece50f912a894c4	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB010774

KNApSAcK ID

Not Available

Chemspider ID

8467119

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10291650

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate (HMDB0032802)

MOL for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D MOL for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D SDF for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D-SDF for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

PDB for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D PDB for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

SMILES for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

INCHI for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

Structure for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

3D Structure for HMDB0032802 (4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra