Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:12:46 UTC

Update Date

2022-03-07 02:53:43 UTC

HMDB ID

HMDB0033480

Secondary Accession Numbers

HMDB33480

Metabolite Identification

Common Name

Graveoline

Description

Graveoline belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Graveoline has been detected, but not quantified in, herbs and spices. This could make graveoline a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Graveoline.

Structure

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

HMDB0033480
     RDKit          3D
Graveoline
 34 37  0  0  0  0  0  0  0  0999 V2000
   -0.7633   -1.6645   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -0.3830   -0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694    0.4277    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508    0.0334    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.6431    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0797   -1.0177    1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.7205    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364   -0.0404   -0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0977    0.3262   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    0.1346   -1.6417 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7046   -0.0690   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2687   -0.9476    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522    1.6500    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    2.0674    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2172    3.1858    1.2850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8096    1.2277    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515    1.5791    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0881    0.7139   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6822   -0.5063   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -0.8764   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.0074   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905   -1.7851   -1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -1.7577   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331   -2.5177   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1267   -0.8984    2.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927   -1.5500    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    0.8588   -1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0629    0.8886   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837   -0.5018   -1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    2.2963    1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4123    2.5431    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1264    0.9969   -0.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4139   -1.2047   -1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185   -1.8382   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  3 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
  9  4  1  0
 21 16  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061307082D          

 21 24  0  0  0  0            999 V2000
    3.3523   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -3.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  4  2  0  0  0  0
 13  5  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18  1  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 20 10  1  0  0  0  0
 20 16  1  0  0  0  0
 21 10  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033480

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO3/c1-18-13-5-3-2-4-12(13)15(19)9-14(18)11-6-7-16-17(8-11)21-10-20-16/h2-9H,10H2,1H3

> <INCHI_KEY>
COBBNRKBTCBWQP-UHFFFAOYSA-N

> <FORMULA>
C17H13NO3

> <MOLECULAR_WEIGHT>
279.29

> <EXACT_MASS>
279.089543287

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.59800509125454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-1-methyl-1,4-dihydroquinolin-4-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.7070003573333334

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.748291591651743

> <JCHEM_PKA_STRONGEST_BASIC>
2.0401098811238483

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
80.70349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
graveoline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033480
     RDKit          3D
Graveoline
 34 37  0  0  0  0  0  0  0  0999 V2000
   -0.7633   -1.6645   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -0.3830   -0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694    0.4277    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508    0.0334    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.6431    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0797   -1.0177    1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.7205    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364   -0.0404   -0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0977    0.3262   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    0.1346   -1.6417 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7046   -0.0690   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2687   -0.9476    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522    1.6500    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    2.0674    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2172    3.1858    1.2850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8096    1.2277    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515    1.5791    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0881    0.7139   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6822   -0.5063   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -0.8764   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.0074   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905   -1.7851   -1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -1.7577   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331   -2.5177   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1267   -0.8984    2.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927   -1.5500    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    0.8588   -1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0629    0.8886   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837   -0.5018   -1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    2.2963    1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4123    2.5431    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1264    0.9969   -0.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4139   -1.2047   -1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185   -1.8382   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  3 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
  9  4  1  0
 21 16  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  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       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.592 -11.313   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259 -12.083   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.592  -9.773   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220  -5.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.259  -9.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.259  -7.463   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -5.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590  -6.693   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.591  -9.003   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      11.592  -6.693   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.126  -4.677   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.126  -7.169   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   13                                                       
CONECT    6    7   11                                                       
CONECT    7    6   16                                                       
CONECT    8   11   17                                                       
CONECT    9   14   15                                                       
CONECT   10   20   21                                                       
CONECT   11    6    8   14                                                  
CONECT   12    4   13   15                                                  
CONECT   13    5   12   18                                                  
CONECT   14    9   11   18                                                  
CONECT   15    9   12   19                                                  
CONECT   16    7   17   20                                                  
CONECT   17    8   16   21                                                  
CONECT   18    1   13   14                                                  
CONECT   19   15                                                            
CONECT   20   10   16                                                       
CONECT   21   10   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0033480
HETATM    1  C1  UNL     1      -0.763  -1.664  -0.748  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.106  -0.383  -0.205  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.169   0.428   0.300  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.251   0.033   0.316  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.735  -0.643   1.408  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.080  -1.018   1.427  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.925  -0.721   0.371  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.436  -0.040  -0.726  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.098   0.326  -0.732  1.00  0.00           C  
HETATM   10  O1  UNL     1       4.474   0.135  -1.642  1.00  0.00           O  
HETATM   11  C9  UNL     1       5.705  -0.069  -0.947  1.00  0.00           C  
HETATM   12  O2  UNL     1       5.269  -0.948   0.094  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.552   1.650   0.810  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.859   2.067   0.819  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.217   3.186   1.285  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.810   1.228   0.299  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.151   1.579   0.274  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.088   0.714  -0.256  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.682  -0.506  -0.762  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.351  -0.876  -0.746  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.409  -0.007  -0.214  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.091  -1.785  -1.806  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.341  -1.758  -0.764  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.133  -2.518  -0.120  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.127  -0.898   2.251  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.493  -1.550   2.268  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.672   0.859  -1.567  1.00  0.00           H  
HETATM   28  H7  UNL     1       6.063   0.889  -0.477  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.484  -0.502  -1.572  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.203   2.296   1.213  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.412   2.543   0.682  1.00  0.00           H  
HETATM   32  H11 UNL     1      -6.126   0.997  -0.270  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.414  -1.205  -1.186  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.018  -1.838  -1.143  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4   13   13
CONECT    4    5    5    9
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8   12
CONECT    8    9    9   10
CONECT    9   27
CONECT   10   11
CONECT   11   12   28   29
CONECT   13   14   30
CONECT   14   15   15   16
CONECT   16   17   17   21
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   20   33
CONECT   20   21   21   34
END

HMDB0033480
     RDKit          3D
Graveoline
 34 37  0  0  0  0  0  0  0  0999 V2000
   -0.7633   -1.6645   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -0.3830   -0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694    0.4277    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508    0.0334    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.6431    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0797   -1.0177    1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9246   -0.7205    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364   -0.0404   -0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0977    0.3262   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    0.1346   -1.6417 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7046   -0.0690   -0.9473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2687   -0.9476    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522    1.6500    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589    2.0674    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2172    3.1858    1.2850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8096    1.2277    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515    1.5791    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0881    0.7139   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6822   -0.5063   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -0.8764   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.0074   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905   -1.7851   -1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -1.7577   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331   -2.5177   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1267   -0.8984    2.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927   -1.5500    2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    0.8588   -1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0629    0.8886   -0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837   -0.5018   -1.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    2.2963    1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4123    2.5431    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1264    0.9969   -0.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4139   -1.2047   -1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185   -1.8382   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  3 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
  9  4  1  0
 21 16  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methyl-2-(3,4-methylenedioxyphenyl)-4(1H)-quinolinone	HMDB
2-(1,3-Benzodioxol-5-yl)-1-methyl-4(1H)-quinolinone, 9ci	HMDB
Alkaloid from ruta angustifolia plant	HMDB
Foliosine	HMDB
Graveolin	HMDB
Rutamine	HMDB

Chemical Formula

C₁₇H₁₃NO₃

Average Molecular Weight

279.29

Monoisotopic Molecular Weight

279.089543287

IUPAC Name

2-(2H-1,3-benzodioxol-5-yl)-1-methyl-1,4-dihydroquinolin-4-one

Traditional Name

graveoline

CAS Registry Number

485-61-0

SMILES

CN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C17H13NO3/c1-18-13-5-3-2-4-12(13)15(19)9-14(18)11-6-7-16-17(8-11)21-10-20-16/h2-9H,10H2,1H3

InChI Key

COBBNRKBTCBWQP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Dihydroquinoline
Benzodioxole
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Azacycle
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:5541 )
Quinoline alkaloids (C10689 )
Quinazoline alkaloids (C10689 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033480)

Cellular substructure

Membrane (HMDB: HMDB0033480)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033480)

Source

Exogenous

Food

Food (HMDB: HMDB0033480)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033480)

Not Available

Nutrient (HMDB: HMDB0033480)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	205 - 205.5 °C	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	0.21 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.71	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	16.75	ChemAxon
pKa (Strongest Basic)	2.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.7 m³·mol⁻¹	ChemAxon
Polarizability	29.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.006	31661259
DarkChem	[M-H]-	164.785	31661259
DeepCCS	[M+H]+	160.556	30932474
DeepCCS	[M-H]-	158.198	30932474
DeepCCS	[M-2H]-	191.084	30932474
DeepCCS	[M+Na]+	166.649	30932474
AllCCS	[M+H]+	163.9	32859911
AllCCS	[M+H-H2O]+	159.9	32859911
AllCCS	[M+NH4]+	167.5	32859911
AllCCS	[M+Na]+	168.6	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	167.4	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Graveoline	CN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C1	3735.0	Standard polar	33892256
Graveoline	CN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C1	2464.2	Standard non polar	33892256
Graveoline	CN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C1	3150.3	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 - Graveoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufr-0390000000-352611e506ed20b6463f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Graveoline 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Graveoline , positive-QTOF	splash10-001i-0490000000-d0db66d5f2efb51cb759	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 10V, Negative-QTOF	splash10-004i-0090000000-d749d0de30e3c73c84e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 20V, Negative-QTOF	splash10-004i-0090000000-65e3894dfa895a4abaf0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 40V, Negative-QTOF	splash10-0ufr-1190000000-30699925815ed3f7bbe8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 10V, Negative-QTOF	splash10-004i-0090000000-8e1bf2c742825f66dfd0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 20V, Negative-QTOF	splash10-004i-0090000000-33097f6056dfc373eda9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 40V, Negative-QTOF	splash10-0f92-0490000000-69166401556d4a9ca8f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 10V, Positive-QTOF	splash10-001i-0090000000-42928c32f520d5fe6358	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 20V, Positive-QTOF	splash10-001i-0090000000-0c5a9e551562449a223f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 40V, Positive-QTOF	splash10-0zfr-1290000000-ae55537f5c75c23e2185	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 10V, Positive-QTOF	splash10-001i-0090000000-830673202d5e6529626e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 20V, Positive-QTOF	splash10-001i-0090000000-a6393bc3b8e399fe9d16	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Graveoline 40V, Positive-QTOF	splash10-0ue9-0490000000-2384bbc28e0732353f49	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

353825

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 Graveoline (HMDB0033480)

MOL for HMDB0033480 (Graveoline)

3D MOL for HMDB0033480 (Graveoline)

3D SDF for HMDB0033480 (Graveoline)

3D-SDF for HMDB0033480 (Graveoline)

PDB for HMDB0033480 (Graveoline)

3D PDB for HMDB0033480 (Graveoline)

SMILES for HMDB0033480 (Graveoline)

INCHI for HMDB0033480 (Graveoline)

Structure for HMDB0033480 (Graveoline)

3D Structure for HMDB0033480 (Graveoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra