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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:36:45 UTC

Update Date

2022-03-07 02:52:32 UTC

HMDB ID

HMDB0030433

Secondary Accession Numbers

HMDB30433

Metabolite Identification

Common Name

Linalyl anthranilate

Description

Linalyl anthranilate belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a small amount of articles have been published on Linalyl anthranilate.

Structure

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

HMDB0030433
     RDKit          3D
Linalyl anthranilate
 43 43  0  0  0  0  0  0  0  0999 V2000
    0.5181   -2.4635    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5838   -1.2502   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -0.0090    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832   -0.3542    2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177    1.1223    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    0.9040    0.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176   -0.1867   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537    0.0654   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250    1.4647   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0666   -1.0108   -1.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    0.4396    0.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -0.2575    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1247   -1.4085    0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4235    0.3023   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5396    1.5506   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7522    2.0332   -1.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8782    1.2472   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7748   -0.0057   -0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517   -0.4720   -0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4647   -1.7655    0.3742 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -2.5699    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7462   -3.3347   -0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -1.1151   -1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394    0.5945    2.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6037   -0.9540    2.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698   -0.9763    2.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8787    1.9919    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820    1.4236   -0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1680    1.8664    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533    0.8783    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0385   -1.2074    0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    1.5066   -1.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532    1.9268   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924    2.0147   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706   -1.9355   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0418   -1.1643   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2906   -0.5956   -2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6599    2.1725   -0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7968    3.0283   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8236    1.6484   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6778   -0.6075   -0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5579   -2.5738   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3201   -1.9636    1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
M  END


  Mrv0541 05061305132D          

 20 20  0  0  0  0            999 V2000
   -0.1914    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030433

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H23NO2/c1-5-17(4,12-8-9-13(2)3)20-16(19)14-10-6-7-11-15(14)18/h5-7,9-11H,1,8,12,18H2,2-4H3

> <INCHI_KEY>
WHIJSULEEDNKPD-UHFFFAOYSA-N

> <FORMULA>
C17H23NO2

> <MOLECULAR_WEIGHT>
273.37

> <EXACT_MASS>
273.172878985

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.100331085961578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethylocta-1,6-dien-3-yl 2-aminobenzoate

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
4.963866347333335

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.37876963594049

> <JCHEM_PKA_STRONGEST_BASIC>
2.177430928633392

> <JCHEM_POLAR_SURFACE_AREA>
52.32000000000001

> <JCHEM_REFRACTIVITY>
84.72899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethylocta-1,6-dien-3-yl 2-aminobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030433
     RDKit          3D
Linalyl anthranilate
 43 43  0  0  0  0  0  0  0  0999 V2000
    0.5181   -2.4635    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5838   -1.2502   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -0.0090    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832   -0.3542    2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177    1.1223    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    0.9040    0.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176   -0.1867   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537    0.0654   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250    1.4647   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0666   -1.0108   -1.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    0.4396    0.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -0.2575    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1247   -1.4085    0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4235    0.3023   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5396    1.5506   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7522    2.0332   -1.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8782    1.2472   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7748   -0.0057   -0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517   -0.4720   -0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4647   -1.7655    0.3742 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -2.5699    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7462   -3.3347   -0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -1.1151   -1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394    0.5945    2.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6037   -0.9540    2.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698   -0.9763    2.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8787    1.9919    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820    1.4236   -0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1680    1.8664    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533    0.8783    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0385   -1.2074    0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    1.5066   -1.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532    1.9268   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924    2.0147   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706   -1.9355   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0418   -1.1643   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2906   -0.5956   -2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6599    2.1725   -0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7968    3.0283   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8236    1.6484   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6778   -0.6075   -0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5579   -2.5738   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3201   -1.9636    1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  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      -0.357   5.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.437   3.286   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.897   5.954   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   17                                                            
CONECT    5    1   17                                                       
CONECT    6    7   10                                                       
CONECT    7    6   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7   15                                                       
CONECT   12    8   17                                                       
CONECT   13    2    3    9                                                  
CONECT   14   10   15   16                                                  
CONECT   15   11   14   18                                                  
CONECT   16   14   19   20                                                  
CONECT   17    4    5   12   20                                             
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0030433
HETATM    1  C1  UNL     1       0.518  -2.464   0.439  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.584  -1.250  -0.095  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.272  -0.009   0.664  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.283  -0.354   2.131  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.218   1.122   0.345  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.649   0.904   0.624  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.318  -0.187  -0.081  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.354   0.065  -0.899  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.825   1.465  -1.090  1.00  0.00           C  
HETATM   10  C10 UNL     1       5.067  -1.011  -1.639  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.983   0.440   0.191  1.00  0.00           O  
HETATM   12  C11 UNL     1      -2.172  -0.257   0.229  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.125  -1.408   0.735  1.00  0.00           O  
HETATM   14  C12 UNL     1      -3.424   0.302  -0.287  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.540   1.551  -0.850  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.752   2.033  -1.325  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.878   1.247  -1.234  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.775  -0.006  -0.672  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.552  -0.472  -0.202  1.00  0.00           C  
HETATM   20  N1  UNL     1      -4.465  -1.766   0.374  1.00  0.00           N  
HETATM   21  H1  UNL     1       0.226  -2.570   1.473  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.746  -3.335  -0.127  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.877  -1.115  -1.136  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.339   0.595   2.734  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.604  -0.954   2.401  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.170  -0.976   2.328  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.879   1.992   0.951  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.082   1.424  -0.712  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.168   1.866   0.328  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.853   0.878   1.740  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.038  -1.207   0.011  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.691   1.507  -1.771  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.153   1.927  -0.136  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.992   2.015  -1.573  1.00  0.00           H  
HETATM   35  H15 UNL     1       4.471  -1.936  -1.716  1.00  0.00           H  
HETATM   36  H16 UNL     1       6.042  -1.164  -1.141  1.00  0.00           H  
HETATM   37  H17 UNL     1       5.291  -0.596  -2.662  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.660   2.173  -0.924  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.797   3.028  -1.763  1.00  0.00           H  
HETATM   40  H20 UNL     1      -6.824   1.648  -1.615  1.00  0.00           H  
HETATM   41  H21 UNL     1      -6.678  -0.607  -0.611  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.558  -2.574  -0.291  1.00  0.00           H  
HETATM   43  H23 UNL     1      -4.320  -1.964   1.375  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   23
CONECT    3    4    5   11
CONECT    4   24   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8    8   31
CONECT    8    9   10
CONECT    9   32   33   34
CONECT   10   35   36   37
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   19
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20
CONECT   20   42   43
END

HMDB0030433
     RDKit          3D
Linalyl anthranilate
 43 43  0  0  0  0  0  0  0  0999 V2000
    0.5181   -2.4635    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5838   -1.2502   -0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -0.0090    0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832   -0.3542    2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177    1.1223    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    0.9040    0.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176   -0.1867   -0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537    0.0654   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250    1.4647   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0666   -1.0108   -1.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    0.4396    0.1910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720   -0.2575    0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1247   -1.4085    0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4235    0.3023   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5396    1.5506   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7522    2.0332   -1.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8782    1.2472   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7748   -0.0057   -0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5517   -0.4720   -0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4647   -1.7655    0.3742 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258   -2.5699    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7462   -3.3347   -0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -1.1151   -1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394    0.5945    2.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6037   -0.9540    2.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1698   -0.9763    2.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8787    1.9919    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820    1.4236   -0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1680    1.8664    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533    0.8783    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0385   -1.2074    0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6908    1.5066   -1.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532    1.9268   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9924    2.0147   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706   -1.9355   -1.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0418   -1.1643   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2906   -0.5956   -2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6599    2.1725   -0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7968    3.0283   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8236    1.6484   -1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6778   -0.6075   -0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5579   -2.5738   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3201   -1.9636    1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Linalyl anthranilic acid	Generator
1, 6-Octadien-3-ol, 3,7-dimethyl-, 2-aminobenzoate	HMDB
1,5-Dimethyl-1-vinyl-4-hexen-1-yl O-aminobenzoate	HMDB
1,5-Dimethyl-1-vinyl-4-hexenyl anthranilate	HMDB
1,5-Dimethyl-1-vinylhex-4-en-1-yl 2-aminobenzoate	HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, 2-aminobenzoate	HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, 3-(2-aminobenzoate)	HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, O-aminobenzoate	HMDB
3, 7-Dimethyl-1,6-octadien-3-yl, anthranilate	HMDB
3,7-Dimethyl-1,6-octadien-3-ol 2-aminobenzoate	HMDB
3,7-Dimethyl-1,6-octadien-3-yl 2-aminobenzoate	HMDB
3,7-Dimethyl-1,6-octadien-3-yl O-aminobenzoate	HMDB
3,7-Dimethyl-1,6-octadien-3-yl, anthranilate	HMDB
4-Hexen-1-ol, 1,5-dimethyl-1-vinyl-, O-aminobenzoate	HMDB
Anthranilic acid, 1, 5-dimethyl-1-vinyl-4-hexenyl ester	HMDB
Anthranilic acid, 1,5-dimethyl-1-vinyl-4-hexenyl ester	HMDB
Anthranilic acid, linalyl ester	HMDB
FEMA 2637	HMDB
Linalyl 2-aminobenzoate	HMDB
Linalyl O-aminobenzoate	HMDB
3,7-Dimethylocta-1,6-dien-3-yl 2-aminobenzoic acid	Generator

Chemical Formula

C₁₇H₂₃NO₂

Average Molecular Weight

273.37

Monoisotopic Molecular Weight

273.172878985

IUPAC Name

3,7-dimethylocta-1,6-dien-3-yl 2-aminobenzoate

Traditional Name

3,7-dimethylocta-1,6-dien-3-yl 2-aminobenzoate

CAS Registry Number

7149-26-0

SMILES

CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C

InChI Identifier

InChI=1S/C17H23NO2/c1-5-17(4,12-8-9-13(2)3)20-16(19)14-10-6-7-11-15(14)18/h5-7,9-11H,1,8,12,18H2,2-4H3

InChI Key

WHIJSULEEDNKPD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Aromatic monoterpenoid
Benzoate ester
Monocyclic monoterpenoid
Benzoic acid or derivatives
Aniline or substituted anilines
Benzoyl
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organopnictogen compound
Amine
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cytoplasm (HMDB: HMDB0030433)
Cell membrane (HMDB: HMDB0030433)

Biofluid or Excreta

Feces (HMDB: HMDB0030433)

Excreta

Biofluid or Excreta

Feces (PMID: 23454028)

Cellular substructure

Extracellular (HMDB: HMDB0030433)
Membrane (HMDB: HMDB0030433)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030433)

Source

Endogenous

Endogenous (HMDB: HMDB0030433)

Animal

Animal (HMDB: HMDB0030433)

Exogenous

Food

Food (HMDB: HMDB0030433)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0030433)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0030433)

Cellular process

Cell signaling (HMDB: HMDB0030433)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0030433)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0030433)

Nutrient

Nutrient (HMDB: HMDB0030433)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030433)

Emulsifier (HMDB: HMDB0030433)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	370.00 to 371.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.076 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.800 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	4.15	ALOGPS
logP	4.96	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	19.38	ChemAxon
pKa (Strongest Basic)	2.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	84.73 m³·mol⁻¹	ChemAxon
Polarizability	31.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.164	31661259
DarkChem	[M-H]-	164.307	31661259
DeepCCS	[M+H]+	167.543	30932474
DeepCCS	[M-H]-	165.185	30932474
DeepCCS	[M-2H]-	198.071	30932474
DeepCCS	[M+Na]+	173.636	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	170.5	32859911
AllCCS	[M+Na]+	171.4	32859911
AllCCS	[M-H]-	171.2	32859911
AllCCS	[M+Na-2H]-	171.4	32859911
AllCCS	[M+HCOO]-	171.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Linalyl anthranilate	CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C	2894.6	Standard polar	33892256
Linalyl anthranilate	CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C	1986.1	Standard non polar	33892256
Linalyl anthranilate	CC(C)=CCCC(C)(OC(=O)C1=CC=CC=C1N)C=C	2068.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Linalyl anthranilate,1TMS,isomer #1	C=CC(C)(CCC=C(C)C)OC(=O)C1=CC=CC=C1N[Si](C)(C)C	2161.1	Semi standard non polar	33892256
Linalyl anthranilate,1TMS,isomer #1	C=CC(C)(CCC=C(C)C)OC(=O)C1=CC=CC=C1N[Si](C)(C)C	2096.5	Standard non polar	33892256
Linalyl anthranilate,2TMS,isomer #1	C=CC(C)(CCC=C(C)C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2136.3	Semi standard non polar	33892256
Linalyl anthranilate,2TMS,isomer #1	C=CC(C)(CCC=C(C)C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2106.0	Standard non polar	33892256
Linalyl anthranilate,1TBDMS,isomer #1	C=CC(C)(CCC=C(C)C)OC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	2344.5	Semi standard non polar	33892256
Linalyl anthranilate,1TBDMS,isomer #1	C=CC(C)(CCC=C(C)C)OC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	2301.6	Standard non polar	33892256
Linalyl anthranilate,2TBDMS,isomer #1	C=CC(C)(CCC=C(C)C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2545.9	Semi standard non polar	33892256
Linalyl anthranilate,2TBDMS,isomer #1	C=CC(C)(CCC=C(C)C)OC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2481.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Linalyl anthranilate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-7900000000-8b372620695c2c09d114	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linalyl anthranilate 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 - Linalyl anthranilate 10V, Positive-QTOF	splash10-00di-1490000000-2ff0836fc2419ebb6d2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 20V, Positive-QTOF	splash10-00di-8930000000-e50baae1ab9a7bd24d2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 40V, Positive-QTOF	splash10-0gi0-9200000000-78eff87cd6542ffe8881	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 10V, Negative-QTOF	splash10-00di-2390000000-b3cb52c5e7311404b800	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 20V, Negative-QTOF	splash10-006x-9780000000-114d30b05b01cf86ce94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 40V, Negative-QTOF	splash10-0006-9700000000-cc4fea34d9c8b24925bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 10V, Positive-QTOF	splash10-00di-2920000000-4c5685da91926f399908	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 20V, Positive-QTOF	splash10-00di-5900000000-de8bbb82b411d2ee1eaa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 40V, Positive-QTOF	splash10-0006-9300000000-0a89e83f27a80cad237c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 10V, Negative-QTOF	splash10-00dl-4690000000-9f23e6e36ae70f498eca	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 20V, Negative-QTOF	splash10-0006-9420000000-64dfe30866d851275fb1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linalyl anthranilate 40V, Negative-QTOF	splash10-0006-9000000000-34859c653b65e95a9058	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Nonalcoholic fatty liver disease	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002297

KNApSAcK ID

Not Available

Chemspider ID

22005

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23535

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1015571

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Linalyl anthranilate (HMDB0030433)

MOL for HMDB0030433 (Linalyl anthranilate)

3D MOL for HMDB0030433 (Linalyl anthranilate)

3D SDF for HMDB0030433 (Linalyl anthranilate)

3D-SDF for HMDB0030433 (Linalyl anthranilate)

PDB for HMDB0030433 (Linalyl anthranilate)

3D PDB for HMDB0030433 (Linalyl anthranilate)

SMILES for HMDB0030433 (Linalyl anthranilate)

INCHI for HMDB0030433 (Linalyl anthranilate)

Structure for HMDB0030433 (Linalyl anthranilate)

3D Structure for HMDB0030433 (Linalyl anthranilate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra