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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:22:58 UTC

Update Date

2022-03-07 02:56:02 UTC

HMDB ID

HMDB0039030

Secondary Accession Numbers

HMDB39030

Metabolite Identification

Common Name

trans-Grandmarin

Description

trans-Grandmarin 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-Grandmarin has been detected, but not quantified in, citrus. This could make trans-grandmarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on trans-Grandmarin.

Structure

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

HMDB0039030
     RDKit          3D
trans-Grandmarin
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.8884    1.7024   -1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763    0.6311   -0.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3821    0.3114   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3107    1.0136   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495    0.6147   -0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -0.4173    0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9240   -1.0957    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -2.0969    1.7622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -2.7581    2.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620   -3.7086    3.0350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -2.4633    1.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084   -1.4210    1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2078   -0.7468    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -0.8395    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -2.0710    0.4034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    0.2189    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6896    1.1250    1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3360    0.9413   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859    2.2100   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    0.0267   -1.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    1.3276   -0.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733    1.9054   -1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    1.3992   -2.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516    2.5931   -1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.8323   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218   -3.0333    2.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023   -1.1438    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881   -0.9219    2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -2.6222    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5540   -0.2907    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3765    0.8074    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293    2.7226    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2556    1.9878   -0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312    2.8791   -1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644   -0.9732   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    0.3686   -2.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569   -0.0151   -1.9310 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
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 13  3  1  0
 21  5  1  0
 13  7  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
M  END


  Mrv0541 02241215002D          

 21 23  0  0  0  0            999 V2000
    2.3393    0.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6826   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9437   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9289   -2.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7646   -1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856   -1.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -1.6415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1900   -1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -1.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869   -1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0258   -1.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1900    2.0520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1900    1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467    0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1900   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511    0.8206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0258    0.8206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3 21  1  0  0  0  0
  4 12  2  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039030

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)C(O)C(C)(C)O2)C2=C1C=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O6/c1-15(2)14(18)12(17)11-9(21-15)6-8(19-3)7-4-5-10(16)20-13(7)11/h4-6,12,14,17-18H,1-3H3

> <INCHI_KEY>
RRUHFAXVNXSPNG-UHFFFAOYSA-N

> <FORMULA>
C15H16O6

> <MOLECULAR_WEIGHT>
292.2839

> <EXACT_MASS>
292.094688244

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.00752773563173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
0.6557261943333333

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.019945750618728

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.575570670664504

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7263091830075945

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
74.0116

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,14-dihydroxy-8-methoxy-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

$$$$

HMDB0039030
     RDKit          3D
trans-Grandmarin
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.8884    1.7024   -1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763    0.6311   -0.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3821    0.3114   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3107    1.0136   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495    0.6147   -0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -0.4173    0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9240   -1.0957    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -2.0969    1.7622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -2.7581    2.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620   -3.7086    3.0350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -2.4633    1.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084   -1.4210    1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2078   -0.7468    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -0.8395    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -2.0710    0.4034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    0.2189    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6896    1.1250    1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3360    0.9413   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859    2.2100   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    0.0267   -1.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    1.3276   -0.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733    1.9054   -1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    1.3992   -2.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516    2.5931   -1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.8323   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218   -3.0333    2.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023   -1.1438    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881   -0.9219    2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -2.6222    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5540   -0.2907    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3765    0.8074    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293    2.7226    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2556    1.9878   -0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312    2.8791   -1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644   -0.9732   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    0.3686   -2.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569   -0.0151   -1.9310 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
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 13  3  1  0
 21  5  1  0
 13  7  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.367   0.153   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.141  -0.766   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.762  -0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.536  -0.766   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.601  -3.830   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.294  -2.298   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.826  -2.145   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.826  -2.451   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.447  -3.064   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.221  -2.298   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.842  -3.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.536  -2.298   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.915  -2.911   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.221   3.830   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.221   2.298   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.447   1.532   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.447  -0.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.221  -0.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.842  -0.001   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.842   1.532   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.915   1.532   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3   12   19                                                  
CONECT    5    6                                                            
CONECT    6    2    5    7   13                                             
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12    4   11   13                                                  
CONECT   13    6   12                                                       
CONECT   14   15                                                            
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   10   17   19                                                  
CONECT   19    4   18   20                                                  
CONECT   20   15   19                                                       
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0039030
HETATM    1  C1  UNL     1       3.888   1.702  -1.568  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.676   0.631  -0.673  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.382   0.311  -0.326  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.311   1.014  -0.834  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.050   0.615  -0.423  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.187  -0.417   0.441  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.924  -1.096   0.927  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.745  -2.097   1.762  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.772  -2.758   2.239  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.562  -3.709   3.035  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.077  -2.463   1.912  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.308  -1.421   1.039  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.208  -0.747   0.556  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.547  -0.839   0.877  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.913  -2.071   0.403  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.561   0.219   0.577  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.690   1.125   1.655  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.336   0.941  -0.707  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.186   2.210  -0.698  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.761   0.027  -1.848  1.00  0.00           C  
HETATM   21  O6  UNL     1      -1.018   1.328  -0.940  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.973   1.905  -1.689  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.479   1.399  -2.553  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.352   2.593  -1.209  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.484   1.832  -1.518  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.922  -3.033   2.326  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.302  -1.144   0.746  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.488  -0.922   2.002  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.187  -2.622   0.051  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.554  -0.291   0.511  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.377   0.807   2.296  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.029   2.723   0.268  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.256   1.988  -0.815  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.831   2.879  -1.505  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.364  -0.973  -1.615  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.272   0.369  -2.774  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.857  -0.015  -1.931  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   25
CONECT    5    6    6   21
CONECT    6    7   14
CONECT    7    8   13   13
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   26
CONECT   12   13   27
CONECT   14   15   16   28
CONECT   15   29
CONECT   16   17   18   30
CONECT   17   31
CONECT   18   19   20   21
CONECT   19   32   33   34
CONECT   20   35   36   37
END

HMDB0039030
     RDKit          3D
trans-Grandmarin
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.8884    1.7024   -1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6763    0.6311   -0.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3821    0.3114   -0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3107    1.0136   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495    0.6147   -0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -0.4173    0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9240   -1.0957    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7449   -2.0969    1.7622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716   -2.7581    2.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5620   -3.7086    3.0350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -2.4633    1.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084   -1.4210    1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2078   -0.7468    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -0.8395    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -2.0710    0.4034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    0.2189    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6896    1.1250    1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3360    0.9413   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859    2.2100   -0.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    0.0267   -1.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    1.3276   -0.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9733    1.9054   -1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    1.3992   -2.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516    2.5931   -1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    1.8323   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9218   -3.0333    2.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023   -1.1438    0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881   -0.9219    2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -2.6222    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5540   -0.2907    0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3765    0.8074    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0293    2.7226    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2556    1.9878   -0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312    2.8791   -1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644   -0.9732   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    0.3686   -2.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569   -0.0151   -1.9310 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
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 13  3  1  0
 21  5  1  0
 13  7  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₆

Average Molecular Weight

292.2839

Monoisotopic Molecular Weight

292.094688244

IUPAC Name

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

Traditional Name

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

CAS Registry Number

119239-48-4

SMILES

COC1=CC2=C(C(O)C(O)C(C)(C)O2)C2=C1C=CC(=O)O2

InChI Identifier

InChI=1S/C15H16O6/c1-15(2)14(18)12(17)11-9(21-15)6-8(19-3)7-4-5-10(16)20-13(7)11/h4-6,12,14,17-18H,1-3H3

InChI Key

RRUHFAXVNXSPNG-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
1,2-diol
Lactone
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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: HMDB0039030)
Cytoplasm (HMDB: HMDB0039030)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039030)

Source

Exogenous

Food

Food (HMDB: HMDB0039030)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0039030)

Not Available

Nutrient (HMDB: HMDB0039030)

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	2815 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.46 g/L	ALOGPS
logP	1.08	ALOGPS
logP	0.66	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.01 m³·mol⁻¹	ChemAxon
Polarizability	29.01 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]+	165.748	31661259
DarkChem	[M-H]-	165.452	31661259
DeepCCS	[M+H]+	168.885	30932474
DeepCCS	[M-H]-	166.528	30932474
DeepCCS	[M-2H]-	199.803	30932474
DeepCCS	[M+Na]+	175.03	30932474
AllCCS	[M+H]+	166.2	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	170.3	32859911
AllCCS	[M+Na-2H]-	170.1	32859911
AllCCS	[M+HCOO]-	169.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-Grandmarin	COC1=CC2=C(C(O)C(O)C(C)(C)O2)C2=C1C=CC(=O)O2	3397.5	Standard polar	33892256
trans-Grandmarin	COC1=CC2=C(C(O)C(O)C(C)(C)O2)C2=C1C=CC(=O)O2	2532.7	Standard non polar	33892256
trans-Grandmarin	COC1=CC2=C(C(O)C(O)C(C)(C)O2)C2=C1C=CC(=O)O2	2680.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-Grandmarin,1TMS,isomer #1	COC1=CC2=C(C3=C1C=CC(=O)O3)C(O[Si](C)(C)C)C(O)C(C)(C)O2	2531.3	Semi standard non polar	33892256
trans-Grandmarin,1TMS,isomer #2	COC1=CC2=C(C3=C1C=CC(=O)O3)C(O)C(O[Si](C)(C)C)C(C)(C)O2	2564.1	Semi standard non polar	33892256
trans-Grandmarin,2TMS,isomer #1	COC1=CC2=C(C3=C1C=CC(=O)O3)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C)O2	2500.3	Semi standard non polar	33892256
trans-Grandmarin,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C=CC(=O)O3)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C)O2	2769.6	Semi standard non polar	33892256
trans-Grandmarin,1TBDMS,isomer #2	COC1=CC2=C(C3=C1C=CC(=O)O3)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C)O2	2824.0	Semi standard non polar	33892256
trans-Grandmarin,2TBDMS,isomer #1	COC1=CC2=C(C3=C1C=CC(=O)O3)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C)O2	2941.9	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 - trans-Grandmarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0090000000-6f833259c7e7d85acfe8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Grandmarin GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8029600000-7682dc0dfad0b75f32d7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Grandmarin 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-Grandmarin 10V, Positive-QTOF	splash10-0006-1090000000-de8617b27009aee670dc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 20V, Positive-QTOF	splash10-0096-1190000000-307fa8f58dfad4477565	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 40V, Positive-QTOF	splash10-05br-7950000000-142f8fd404e2eb04d6b0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 10V, Negative-QTOF	splash10-0006-0090000000-abdac1e8dd149dc33169	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 20V, Negative-QTOF	splash10-00r6-2090000000-d4dde72f28bb56b749c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 40V, Negative-QTOF	splash10-0597-4940000000-6f603aa7ca7662ced912	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 10V, Negative-QTOF	splash10-0006-0090000000-e2531b222357475903f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 20V, Negative-QTOF	splash10-0006-0190000000-c9bde112cdfa8edf70e6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 40V, Negative-QTOF	splash10-000i-1390000000-fa33b8c763b176b0e1d8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 10V, Positive-QTOF	splash10-0006-0090000000-27a50d8d1b5d00ef062c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 20V, Positive-QTOF	splash10-0006-0090000000-c5b7023a44861db74a1e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Grandmarin 40V, Positive-QTOF	splash10-0006-3690000000-01fb624888424a91a91d	2021-09-24	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

FDB018526

KNApSAcK ID

C00019881

Chemspider ID

28282480

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14213970

PDB ID

Not Available

ChEBI ID

168055

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1873671

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-Grandmarin (HMDB0039030)

MOL for HMDB0039030 (trans-Grandmarin)

3D MOL for HMDB0039030 (trans-Grandmarin)

3D SDF for HMDB0039030 (trans-Grandmarin)

3D-SDF for HMDB0039030 (trans-Grandmarin)

PDB for HMDB0039030 (trans-Grandmarin)

3D PDB for HMDB0039030 (trans-Grandmarin)

SMILES for HMDB0039030 (trans-Grandmarin)

INCHI for HMDB0039030 (trans-Grandmarin)

Structure for HMDB0039030 (trans-Grandmarin)

3D Structure for HMDB0039030 (trans-Grandmarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra