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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:23:01 UTC

Update Date

2022-03-07 02:56:02 UTC

HMDB ID

HMDB0039031

Secondary Accession Numbers

HMDB39031

Metabolite Identification

Common Name

trans-O-Methylgrandmarin

Description

trans-O-Methylgrandmarin belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. trans-O-Methylgrandmarin has been detected, but not quantified in, citrus. This could make trans-O-methylgrandmarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on trans-O-Methylgrandmarin.

Structure

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

HMDB0039031
     RDKit          3D
trans-O-Methylgrandmarin
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.7467   -3.0283    0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.6215    0.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5504   -0.9494    0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585   -1.6624    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -1.0014    0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.3868    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846    1.1213    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157    2.4250    0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    3.1532    0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468    4.4300    0.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    2.5165    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451    1.1414    0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837    0.4237    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675    1.1055   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    1.3187   -1.4505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657    2.6430   -1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.3110    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133    0.8552   -0.0387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045   -1.1398    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9652   -1.2908   -1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1646   -1.9572    1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196   -1.6928   -0.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213   -3.3706    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7934   -3.4095    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694   -3.4704   -0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -2.7582    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4946    3.1079    0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5890    0.5946    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    2.0402    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750    2.7037   -2.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    3.1792   -1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695    3.1400   -1.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    0.4183    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    1.0149   -1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9860   -0.9140   -1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447   -0.7598   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -2.3923   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726   -1.5578    2.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -2.0680    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7062   -2.9860    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 13  3  1  0
 22  5  1  0
 13  7  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
M  END


  Mrv0541 05061310482D          

 22 24  0  0  0  0            999 V2000
    4.6465   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  2  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19  9  1  0  0  0  0
 20  4  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 13  1  0  0  0  0
 22 10  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039031

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C(O)C(C)(C)OC2=C1C1=C(C=CC(=O)O1)C(OC)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O6/c1-16(2)15(18)14(20-4)12-10(22-16)7-9(19-3)8-5-6-11(17)21-13(8)12/h5-7,14-15,18H,1-4H3

> <INCHI_KEY>
NACAFQOYZHTCHZ-UHFFFAOYSA-N

> <FORMULA>
C16H18O6

> <MOLECULAR_WEIGHT>
306.3105

> <EXACT_MASS>
306.110338308

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.968520770735054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-hydroxy-8,14-dimethoxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-4-one

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.2988526980000001

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.864675124393546

> <JCHEM_PKA_STRONGEST_BASIC>
-3.732791100590263

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
78.76280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxy-8,14-dimethoxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039031
     RDKit          3D
trans-O-Methylgrandmarin
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.7467   -3.0283    0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.6215    0.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5504   -0.9494    0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585   -1.6624    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -1.0014    0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.3868    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846    1.1213    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157    2.4250    0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    3.1532    0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468    4.4300    0.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    2.5165    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451    1.1414    0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837    0.4237    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675    1.1055   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    1.3187   -1.4505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657    2.6430   -1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.3110    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133    0.8552   -0.0387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045   -1.1398    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9652   -1.2908   -1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1646   -1.9572    1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196   -1.6928   -0.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213   -3.3706    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7934   -3.4095    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694   -3.4704   -0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -2.7582    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4946    3.1079    0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5890    0.5946    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    2.0402    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750    2.7037   -2.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    3.1792   -1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695    3.1400   -1.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    0.4183    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    1.0149   -1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9860   -0.9140   -1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447   -0.7598   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -2.3923   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726   -1.5578    2.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -2.0680    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7062   -2.9860    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 13  3  1  0
 22  5  1  0
 13  7  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.673  -4.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673  -2.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   0.151   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -7.851   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -1.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.494  -6.517   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.104   0.151   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.414  -6.517   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.104  -5.184   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.724  -2.516   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7    9   10                                                       
CONECT    8    5    9   13                                                  
CONECT    9    7    8   19                                                  
CONECT   10    7   12   22                                                  
CONECT   11    6   17   21                                                  
CONECT   12   10   13   14                                                  
CONECT   13    8   12   21                                                  
CONECT   14   12   15   20                                                  
CONECT   15   14   16   18                                                  
CONECT   16    1    2   15   22                                             
CONECT   17   11                                                            
CONECT   18   15                                                            
CONECT   19    3    9                                                       
CONECT   20    4   14                                                       
CONECT   21   11   13                                                       
CONECT   22   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0039031
HETATM    1  C1  UNL     1       3.747  -3.028   0.691  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.726  -1.622   0.648  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.550  -0.949   0.464  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.358  -1.662   0.318  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.164  -1.001   0.132  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.127   0.387   0.087  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.285   1.121   0.228  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.316   2.425   0.195  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.396   3.153   0.324  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.347   4.430   0.281  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.602   2.516   0.511  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.645   1.141   0.557  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.484   0.424   0.415  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.168   1.106  -0.111  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.428   1.319  -1.450  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.566   2.643  -1.793  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.320   0.311   0.455  1.00  0.00           C  
HETATM   18  O5  UNL     1      -3.513   0.855  -0.039  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.304  -1.140   0.130  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.965  -1.291  -1.249  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.165  -1.957   1.075  1.00  0.00           C  
HETATM   22  O6  UNL     1      -1.020  -1.693  -0.013  1.00  0.00           O  
HETATM   23  H1  UNL     1       3.121  -3.371   1.537  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.793  -3.409   0.741  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.269  -3.470  -0.230  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.402  -2.758   0.356  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.495   3.108   0.619  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.589   0.595   0.704  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.108   2.040   0.484  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.775   2.704  -2.893  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.371   3.179  -1.282  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.570   3.140  -1.666  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.333   0.418   1.560  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.367   1.015  -1.005  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.986  -0.914  -1.229  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.345  -0.760  -1.988  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.029  -2.392  -1.475  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.173  -1.558   2.098  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.207  -2.068   0.713  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.706  -2.986   1.097  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   26
CONECT    5    6    6   22
CONECT    6    7   14
CONECT    7    8   13   13
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   14   15   17   29
CONECT   15   16
CONECT   16   30   31   32
CONECT   17   18   19   33
CONECT   18   34
CONECT   19   20   21   22
CONECT   20   35   36   37
CONECT   21   38   39   40
END

HMDB0039031
     RDKit          3D
trans-O-Methylgrandmarin
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.7467   -3.0283    0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -1.6215    0.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5504   -0.9494    0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585   -1.6624    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -1.0014    0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    0.3868    0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846    1.1213    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157    2.4250    0.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    3.1532    0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468    4.4300    0.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    2.5165    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451    1.1414    0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837    0.4237    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675    1.1055   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    1.3187   -1.4505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657    2.6430   -1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.3110    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133    0.8552   -0.0387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045   -1.1398    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9652   -1.2908   -1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1646   -1.9572    1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196   -1.6928   -0.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213   -3.3706    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7934   -3.4095    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694   -3.4704   -0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -2.7582    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4946    3.1079    0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5890    0.5946    0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    2.0402    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750    2.7037   -2.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    3.1792   -1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695    3.1400   -1.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    0.4183    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3666    1.0149   -1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9860   -0.9140   -1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447   -0.7598   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -2.3923   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726   -1.5578    2.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -2.0680    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7062   -2.9860    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 13  3  1  0
 22  5  1  0
 13  7  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₆

Average Molecular Weight

306.3105

Monoisotopic Molecular Weight

306.110338308

IUPAC Name

13-hydroxy-8,14-dimethoxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-4-one

Traditional Name

13-hydroxy-8,14-dimethoxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-4-one

CAS Registry Number

Not Available

SMILES

COC1C(O)C(C)(C)OC2=C1C1=C(C=CC(=O)O1)C(OC)=C2

InChI Identifier

InChI=1S/C16H18O6/c1-16(2)15(18)14(20-4)12-10(22-16)7-9(19-3)8-5-6-11(17)21-13(8)12/h5-7,14-15,18H,1-4H3

InChI Key

NACAFQOYZHTCHZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Secondary alcohol
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039031)
Cytoplasm (HMDB: HMDB0039031)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039031)

Source

Exogenous

Food

Food (HMDB: HMDB0039031)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0039031)

Not Available

Nutrient (HMDB: HMDB0039031)

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	0.64 g/L	ALOGPS
logP	1.89	ALOGPS
logP	1.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.76 m³·mol⁻¹	ChemAxon
Polarizability	30.97 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	170.591	31661259
DarkChem	[M-H]-	169.952	31661259
DeepCCS	[M+H]+	173.716	30932474
DeepCCS	[M-H]-	171.358	30932474
DeepCCS	[M-2H]-	204.85	30932474
DeepCCS	[M+Na]+	180.382	30932474
AllCCS	[M+H]+	169.7	32859911
AllCCS	[M+H-H2O]+	166.2	32859911
AllCCS	[M+NH4]+	172.9	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.4	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-O-Methylgrandmarin	COC1C(O)C(C)(C)OC2=C1C1=C(C=CC(=O)O1)C(OC)=C2	3397.8	Standard polar	33892256
trans-O-Methylgrandmarin	COC1C(O)C(C)(C)OC2=C1C1=C(C=CC(=O)O1)C(OC)=C2	2397.3	Standard non polar	33892256
trans-O-Methylgrandmarin	COC1C(O)C(C)(C)OC2=C1C1=C(C=CC(=O)O1)C(OC)=C2	2620.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-O-Methylgrandmarin,1TMS,isomer #1	COC1=CC2=C(C3=C1C=CC(=O)O3)C(OC)C(O[Si](C)(C)C)C(C)(C)O2	2504.0	Semi standard non polar	33892256
trans-O-Methylgrandmarin,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C=CC(=O)O3)C(OC)C(O[Si](C)(C)C(C)(C)C)C(C)(C)O2	2748.5	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 - trans-O-Methylgrandmarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0090000000-b9755a6e2dc2e45b3b8f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-O-Methylgrandmarin GC-MS (1 TMS) - 70eV, Positive	splash10-024s-7039000000-52987b2e9cc33d62f080	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-O-Methylgrandmarin 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 - trans-O-Methylgrandmarin 10V, Positive-QTOF	splash10-0a4i-0029000000-cc6f3ae197e482dcd01a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 20V, Positive-QTOF	splash10-0550-1093000000-36041fdb3a0c9e940da3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 40V, Positive-QTOF	splash10-0a4u-2390000000-3ef5a018a9fe7b375b97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 10V, Negative-QTOF	splash10-0a4i-0039000000-3cf572d36fda92a94d1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 20V, Negative-QTOF	splash10-0a5i-1193000000-43cf73e5833609fcbf13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 40V, Negative-QTOF	splash10-05tf-7490000000-55292a72f7da2b3e721e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 10V, Negative-QTOF	splash10-0a4i-0009000000-1da9cc08a33365dc03b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 20V, Negative-QTOF	splash10-0a4i-0198000000-6241b93e18ad2bdd11d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 40V, Negative-QTOF	splash10-0ugi-2590000000-f5d54f4d99ea8c25568f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 10V, Positive-QTOF	splash10-0a4i-0009000000-dabbcb859ddd1c5c0d39	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 20V, Positive-QTOF	splash10-0a4i-0189000000-ee5260811f669e61f796	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-O-Methylgrandmarin 40V, Positive-QTOF	splash10-0006-3790000000-91cd2f7ab8f4ac0c9491	2021-09-22	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

FDB018527

KNApSAcK ID

C00019964

Chemspider ID

35014724

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14429496

PDB ID

Not Available

ChEBI ID

168777

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 trans-O-Methylgrandmarin (HMDB0039031)

MOL for HMDB0039031 (trans-O-Methylgrandmarin)

3D MOL for HMDB0039031 (trans-O-Methylgrandmarin)

3D SDF for HMDB0039031 (trans-O-Methylgrandmarin)

3D-SDF for HMDB0039031 (trans-O-Methylgrandmarin)

PDB for HMDB0039031 (trans-O-Methylgrandmarin)

3D PDB for HMDB0039031 (trans-O-Methylgrandmarin)

SMILES for HMDB0039031 (trans-O-Methylgrandmarin)

INCHI for HMDB0039031 (trans-O-Methylgrandmarin)

Structure for HMDB0039031 (trans-O-Methylgrandmarin)

3D Structure for HMDB0039031 (trans-O-Methylgrandmarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra