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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:48:29 UTC

Update Date

2022-03-07 02:53:16 UTC

HMDB ID

HMDB0032208

Secondary Accession Numbers

HMDB32208

Metabolite Identification

Common Name

Citronellyl anthranilate

Description

Citronellyl 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 Citronellyl anthranilate.

Structure

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

HMDB0032208
     RDKit          3D
Citronellyl anthranilate
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.6365    0.1262    0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135   -0.6919   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6400   -1.4988   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -0.8141   -1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9941   -0.2393   -0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401    0.5536    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618    1.1839    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939    1.9552    1.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    0.2147    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    0.9519    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694    0.0371    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789    0.4964    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6089    1.7460    0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6298   -0.3764   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5438   -1.7303   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6765   -2.5342   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9177   -1.9385   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0385   -0.5810   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8859    0.1836    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0752    1.5925    0.2347 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9703   -0.0038    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6705   -0.1003    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7930    1.1897    0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1271   -1.8999    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3165   -0.7627   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -2.3009   -1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093   -1.5465   -1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021   -1.1450   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    0.3929   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8182   -0.1516    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988    1.3229    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958    1.9324   -0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007    2.4158    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269    1.3069    2.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804    2.8032    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.5837    0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605   -0.2896   -0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252    1.7363   -0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1716    1.3588    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5664   -2.1711   -0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5890   -3.6080   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7879   -2.5815   -0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0317   -0.1578   -0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3347    1.9143    1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9676    2.2925   -0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 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
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
M  END


  Mrv0541 05061306242D          

 20 20  0  0  0  0            999 V2000
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  7  2  0  0  0  0
 14  3  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  2  0  0  0  0
 16 15  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 12  1  0  0  0  0
 20 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032208

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO2/c1-13(2)7-6-8-14(3)11-12-20-17(19)15-9-4-5-10-16(15)18/h4-5,7,9-10,14H,6,8,11-12,18H2,1-3H3

> <INCHI_KEY>
LSJVFMHIFWWGDY-UHFFFAOYSA-N

> <FORMULA>
C17H25NO2

> <MOLECULAR_WEIGHT>
275.3859

> <EXACT_MASS>
275.188529049

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.84059944225151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyloct-6-en-1-yl 2-aminobenzoate

> <ALOGPS_LOGP>
5.00

> <JCHEM_LOGP>
5.068429212

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.3983276109142

> <JCHEM_PKA_STRONGEST_BASIC>
2.2290119787257257

> <JCHEM_POLAR_SURFACE_AREA>
52.32000000000001

> <JCHEM_REFRACTIVITY>
85.00849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyloct-6-en-1-yl 2-aminobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032208
     RDKit          3D
Citronellyl anthranilate
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.6365    0.1262    0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135   -0.6919   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6400   -1.4988   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -0.8141   -1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9941   -0.2393   -0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401    0.5536    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618    1.1839    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939    1.9552    1.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    0.2147    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    0.9519    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694    0.0371    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789    0.4964    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6089    1.7460    0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6298   -0.3764   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5438   -1.7303   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6765   -2.5342   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9177   -1.9385   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0385   -0.5810   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8859    0.1836    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0752    1.5925    0.2347 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9703   -0.0038    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6705   -0.1003    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7930    1.1897    0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1271   -1.8999    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3165   -0.7627   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -2.3009   -1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093   -1.5465   -1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021   -1.1450   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    0.3929   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8182   -0.1516    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988    1.3229    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958    1.9324   -0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007    2.4158    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269    1.3069    2.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804    2.8032    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.5837    0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605   -0.2896   -0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252    1.7363   -0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1716    1.3588    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5664   -2.1711   -0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5890   -3.6080   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7879   -2.5815   -0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0317   -0.1578   -0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3347    1.9143    1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9676    2.2925   -0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 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
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  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       2.667  13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.338  13.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.004  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.671  11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.671  13.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      13.337  13.860   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      13.337   9.240   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003  11.550   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    7    8                                                       
CONECT    7    6   13                                                       
CONECT    8    6   14                                                       
CONECT    9    4   15                                                       
CONECT   10    5   16                                                       
CONECT   11   12   14                                                       
CONECT   12   11   20                                                       
CONECT   13    1    2    7                                                  
CONECT   14    3    8   11                                                  
CONECT   15    9   16   17                                                  
CONECT   16   10   15   18                                                  
CONECT   17   15   19   20                                                  
CONECT   18   16                                                            
CONECT   19   17                                                            
CONECT   20   12   17                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0032208
HETATM    1  C1  UNL     1       5.637   0.126   0.864  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.413  -0.692  -0.331  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.640  -1.499  -0.773  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.345  -0.814  -1.038  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.994  -0.239  -0.966  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.740   0.554   0.231  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.362   1.184   0.298  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.294   1.955   1.598  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.246   0.215   0.142  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.071   0.952   0.225  1.00  0.00           C  
HETATM   11  O1  UNL     1      -2.169   0.037   0.077  1.00  0.00           O  
HETATM   12  C11 UNL     1      -3.479   0.496   0.121  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.609   1.746   0.297  1.00  0.00           O  
HETATM   14  C12 UNL     1      -4.630  -0.376  -0.021  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.544  -1.730  -0.212  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.677  -2.534  -0.345  1.00  0.00           C  
HETATM   17  C15 UNL     1      -6.918  -1.938  -0.281  1.00  0.00           C  
HETATM   18  C16 UNL     1      -7.038  -0.581  -0.090  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.886   0.184   0.038  1.00  0.00           C  
HETATM   20  N1  UNL     1      -6.075   1.593   0.235  1.00  0.00           N  
HETATM   21  H1  UNL     1       4.970  -0.004   1.705  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.670  -0.100   1.325  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.793   1.190   0.530  1.00  0.00           H  
HETATM   24  H4  UNL     1       7.127  -1.900   0.140  1.00  0.00           H  
HETATM   25  H5  UNL     1       7.317  -0.763  -1.221  1.00  0.00           H  
HETATM   26  H6  UNL     1       6.347  -2.301  -1.450  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.509  -1.547  -1.925  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.302  -1.145  -1.061  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.866   0.393  -1.889  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.818  -0.152   1.119  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.499   1.323   0.373  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.296   1.932  -0.516  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.301   2.416   1.739  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.127   1.307   2.469  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.580   2.803   1.544  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.216  -0.584   0.900  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.260  -0.290  -0.845  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.125   1.736  -0.545  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.172   1.359   1.254  1.00  0.00           H  
HETATM   40  H20 UNL     1      -3.566  -2.171  -0.259  1.00  0.00           H  
HETATM   41  H21 UNL     1      -5.589  -3.608  -0.496  1.00  0.00           H  
HETATM   42  H22 UNL     1      -7.788  -2.581  -0.386  1.00  0.00           H  
HETATM   43  H23 UNL     1      -8.032  -0.158  -0.046  1.00  0.00           H  
HETATM   44  H24 UNL     1      -6.335   1.914   1.191  1.00  0.00           H  
HETATM   45  H25 UNL     1      -5.968   2.292  -0.518  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24   25   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8    9   32
CONECT    8   33   34   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   19
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   17   18   42
CONECT   18   19   19   43
CONECT   19   20
CONECT   20   44   45
END

HMDB0032208
     RDKit          3D
Citronellyl anthranilate
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.6365    0.1262    0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135   -0.6919   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6400   -1.4988   -0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -0.8141   -1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9941   -0.2393   -0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401    0.5536    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618    1.1839    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939    1.9552    1.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    0.2147    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    0.9519    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694    0.0371    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789    0.4964    0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6089    1.7460    0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6298   -0.3764   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5438   -1.7303   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6765   -2.5342   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9177   -1.9385   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0385   -0.5810   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8859    0.1836    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0752    1.5925    0.2347 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9703   -0.0038    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6705   -0.1003    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7930    1.1897    0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1271   -1.8999    0.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3165   -0.7627   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -2.3009   -1.4500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093   -1.5465   -1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021   -1.1450   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    0.3929   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8182   -0.1516    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988    1.3229    0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958    1.9324   -0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007    2.4158    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269    1.3069    2.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804    2.8032    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.5837    0.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605   -0.2896   -0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252    1.7363   -0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1716    1.3588    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5664   -2.1711   -0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5890   -3.6080   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7879   -2.5815   -0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0317   -0.1578   -0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3347    1.9143    1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9676    2.2925   -0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 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
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citronellyl anthranilic acid	Generator
2-Aminobenzoate	HMDB
3,7-Dimethyloct-6-enyl 2-aminobenzoate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, 1-(2-aminobenzoate)	HMDB
6-Octen-1-ol, 3,7-dimethyl-, 2-aminobenzoate	HMDB
O-Aminobenzoic acid	HMDB
3,7-Dimethyloct-6-en-1-yl 2-aminobenzoic acid	Generator

Chemical Formula

C₁₇H₂₅NO₂

Average Molecular Weight

275.3859

Monoisotopic Molecular Weight

275.188529049

IUPAC Name

3,7-dimethyloct-6-en-1-yl 2-aminobenzoate

Traditional Name

3,7-dimethyloct-6-en-1-yl 2-aminobenzoate

CAS Registry Number

68555-57-7

SMILES

CC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C

InChI Identifier

InChI=1S/C17H25NO2/c1-13(2)7-6-8-14(3)11-12-20-17(19)15-9-4-5-10-16(15)18/h4-5,7,9-10,14H,6,8,11-12,18H2,1-3H3

InChI Key

LSJVFMHIFWWGDY-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: HMDB0032208)
Cell membrane (HMDB: HMDB0032208)

Cellular substructure

Organelle

Mitochondria

Mitochondria (HMDB: HMDB0032208)

Extracellular (HMDB: HMDB0032208)
Membrane (HMDB: HMDB0032208)

Excreta

Biofluid or Excreta

Feces (PMID: 27015276)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032208)

Source

Endogenous

Endogenous (HMDB: HMDB0032208)

Animal

Animal (HMDB: HMDB0032208)

Exogenous

Food

Food (HMDB: HMDB0032208)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0032208)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0032208)

Cellular process

Cell signaling (HMDB: HMDB0032208)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0032208)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032208)

Nutrient

Nutrient (HMDB: HMDB0032208)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032208)

Emulsifier (HMDB: HMDB0032208)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	365.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.053 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.108 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0064 g/L	ALOGPS
logP	5	ALOGPS
logP	5.07	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.4	ChemAxon
pKa (Strongest Basic)	2.23	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	8	ChemAxon
Refractivity	85.01 m³·mol⁻¹	ChemAxon
Polarizability	32.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	167.179	31661259
DarkChem	[M-H]-	165.638	31661259
DeepCCS	[M+H]+	169.872	30932474
DeepCCS	[M-H]-	167.514	30932474
DeepCCS	[M-2H]-	200.4	30932474
DeepCCS	[M+Na]+	175.965	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	171.8	32859911
AllCCS	[M+Na]+	172.7	32859911
AllCCS	[M-H]-	172.8	32859911
AllCCS	[M+Na-2H]-	173.3	32859911
AllCCS	[M+HCOO]-	174.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citronellyl anthranilate	CC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C	3178.4	Standard polar	33892256
Citronellyl anthranilate	CC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C	2049.6	Standard non polar	33892256
Citronellyl anthranilate	CC(CCOC(=O)C1=CC=CC=C1N)CCC=C(C)C	2208.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citronellyl anthranilate,1TMS,isomer #1	CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C	2311.7	Semi standard non polar	33892256
Citronellyl anthranilate,1TMS,isomer #1	CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C	2266.6	Standard non polar	33892256
Citronellyl anthranilate,2TMS,isomer #1	CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2250.9	Semi standard non polar	33892256
Citronellyl anthranilate,2TMS,isomer #1	CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2254.9	Standard non polar	33892256
Citronellyl anthranilate,1TBDMS,isomer #1	CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	2493.3	Semi standard non polar	33892256
Citronellyl anthranilate,1TBDMS,isomer #1	CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	2468.8	Standard non polar	33892256
Citronellyl anthranilate,2TBDMS,isomer #1	CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2661.7	Semi standard non polar	33892256
Citronellyl anthranilate,2TBDMS,isomer #1	CC(C)=CCCC(C)CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2640.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl anthranilate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4900000000-e33b66f36c4c3a5ad1b9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl 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 - Citronellyl anthranilate 10V, Positive-QTOF	splash10-056r-0490000000-441d0ef74bf986ae4edf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 20V, Positive-QTOF	splash10-05g0-5920000000-89c5a4927181868e4337	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 40V, Positive-QTOF	splash10-0q29-9300000000-2d4d820c7133e8bdf656	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 10V, Negative-QTOF	splash10-00di-2490000000-b894d45998fbd7509f8e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 20V, Negative-QTOF	splash10-000f-7920000000-8d8c356b5d5cb87786df	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 40V, Negative-QTOF	splash10-0006-9400000000-998936f8493c00df96f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 10V, Negative-QTOF	splash10-00di-0090000000-eea24882311fb034a161	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 20V, Negative-QTOF	splash10-0006-9310000000-8081f343081f304b9ef3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 40V, Negative-QTOF	splash10-0006-9000000000-cda295e2422a06c522fb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 10V, Positive-QTOF	splash10-00fr-2940000000-0c7a751677e5245efaf0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 20V, Positive-QTOF	splash10-00e9-8910000000-dea508961b7816e7b46a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl anthranilate 40V, Positive-QTOF	splash10-00ec-9500000000-ad776ace980b2f1eded2	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)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009193

KNApSAcK ID

Not Available

Chemspider ID

98418

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

109467

PDB ID

Not Available

ChEBI ID

172321

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1004401

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 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Citronellyl anthranilate (HMDB0032208)

MOL for HMDB0032208 (Citronellyl anthranilate)

3D MOL for HMDB0032208 (Citronellyl anthranilate)

3D SDF for HMDB0032208 (Citronellyl anthranilate)

3D-SDF for HMDB0032208 (Citronellyl anthranilate)

PDB for HMDB0032208 (Citronellyl anthranilate)

3D PDB for HMDB0032208 (Citronellyl anthranilate)

SMILES for HMDB0032208 (Citronellyl anthranilate)

INCHI for HMDB0032208 (Citronellyl anthranilate)

Structure for HMDB0032208 (Citronellyl anthranilate)

3D Structure for HMDB0032208 (Citronellyl anthranilate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra