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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:10:59 UTC

Update Date

2022-03-07 02:54:47 UTC

HMDB ID

HMDB0036117

Secondary Accession Numbers

HMDB36117

Metabolite Identification

Common Name

(1'R)-Nepetalic acid

Description

(1'R)-Nepetalic acid, also known as (1'r)-nepetalate, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Based on a literature review a small amount of articles have been published on (1'R)-Nepetalic acid.

Structure

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

HMDB0036117
     RDKit          3D
(1'R)-Nepetalic acid
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.7192   -0.8034   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7777    0.1780    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3404    1.5242   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    1.8055    0.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4228   -0.0579   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -1.4901   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535   -1.4686    0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307   -0.2348    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655   -0.4166   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.7414   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209    1.5743    1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5390    1.6154    1.7484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805    2.3546    1.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2976   -1.0500   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7141   -0.3428   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9051   -1.7022   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9009   -0.0468    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461    2.2342   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    0.0867   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -2.1054    0.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564   -1.9103   -1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394   -2.3302    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.3169    1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4702    0.1179    1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266   -0.6534   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2768   -1.2334   -1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078    0.5022   -1.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0486    1.4109   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689    3.0176    0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
M  END


  Mrv0541 05061308532D          

 13 13  0  0  0  0            999 V2000
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036117

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C=O)C1CCC(C)C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O3/c1-6-3-4-8(7(2)5-11)9(6)10(12)13/h5-9H,3-4H2,1-2H3,(H,12,13)

> <INCHI_KEY>
RGTMAXSVLBZNEL-UHFFFAOYSA-N

> <FORMULA>
C10H16O3

> <MOLECULAR_WEIGHT>
184.2322

> <EXACT_MASS>
184.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.707304454418164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-(1-oxopropan-2-yl)cyclopentane-1-carboxylic acid

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.5283229569999999

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.781312767135166

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.58628709299067

> <JCHEM_PKA_STRONGEST_BASIC>
-7.021079775119606

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
48.257600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-(1-oxopropan-2-yl)cyclopentane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036117
     RDKit          3D
(1'R)-Nepetalic acid
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.7192   -0.8034   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7777    0.1780    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3404    1.5242   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    1.8055    0.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4228   -0.0579   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -1.4901   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535   -1.4686    0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307   -0.2348    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655   -0.4166   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.7414   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209    1.5743    1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5390    1.6154    1.7484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805    2.3546    1.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2976   -1.0500   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7141   -0.3428   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9051   -1.7022   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9009   -0.0468    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461    2.2342   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    0.0867   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -2.1054    0.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564   -1.9103   -1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394   -2.3302    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.3169    1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4702    0.1179    1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266   -0.6534   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2768   -1.2334   -1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078    0.5022   -1.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0486    1.4109   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689    3.0176    0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  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      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.795   0.620   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    4    6                                                       
CONECT    4    3    8                                                       
CONECT    5    7   11                                                       
CONECT    6    1    3    9                                                  
CONECT    7    2    5    8                                                  
CONECT    8    4    7    9                                                  
CONECT    9    6    8   10                                                  
CONECT   10    9   12   13                                                  
CONECT   11    5                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0036117
HETATM    1  C1  UNL     1      -2.719  -0.803  -0.721  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.778   0.178   0.018  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.340   1.524  -0.274  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.397   1.805   0.250  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.423  -0.058  -0.563  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.059  -1.490  -0.305  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.054  -1.469   0.684  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.831  -0.235   0.276  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.666  -0.417  -0.945  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.704   0.741  -0.067  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.521   1.574   1.117  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.539   1.615   1.748  1.00  0.00           O  
HETATM   13  O3  UNL     1       1.580   2.355   1.555  1.00  0.00           O  
HETATM   14  H1  UNL     1      -2.298  -1.050  -1.699  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.714  -0.343  -0.897  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.905  -1.702  -0.099  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.901  -0.047   1.077  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.846   2.234  -0.920  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.569   0.087  -1.689  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.917  -2.105   0.044  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.356  -1.910  -1.256  1.00  0.00           H  
HETATM   22  H9  UNL     1       1.739  -2.330   0.611  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.656  -1.317   1.700  1.00  0.00           H  
HETATM   24  H11 UNL     1       2.470   0.118   1.097  1.00  0.00           H  
HETATM   25  H12 UNL     1       3.727  -0.653  -0.697  1.00  0.00           H  
HETATM   26  H13 UNL     1       2.277  -1.233  -1.590  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.708   0.502  -1.576  1.00  0.00           H  
HETATM   28  H15 UNL     1       1.049   1.411  -0.924  1.00  0.00           H  
HETATM   29  H16 UNL     1       2.069   3.018   0.954  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    5   17
CONECT    3    4    4   18
CONECT    5    6   10   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9   10   24
CONECT    9   25   26   27
CONECT   10   11   28
CONECT   11   12   12   13
CONECT   13   29
END

HMDB0036117
     RDKit          3D
(1'R)-Nepetalic acid
 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.7192   -0.8034   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7777    0.1780    0.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3404    1.5242   -0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    1.8055    0.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4228   -0.0579   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -1.4901   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535   -1.4686    0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307   -0.2348    0.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655   -0.4166   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.7414   -0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5209    1.5743    1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5390    1.6154    1.7484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805    2.3546    1.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2976   -1.0500   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7141   -0.3428   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9051   -1.7022   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9009   -0.0468    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461    2.2342   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    0.0867   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -2.1054    0.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564   -1.9103   -1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394   -2.3302    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.3169    1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4702    0.1179    1.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266   -0.6534   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2768   -1.2334   -1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078    0.5022   -1.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0486    1.4109   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689    3.0176    0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1'r)-Nepetalate	Generator
trans-1,2,trans-1,5-2-(1-Formylethyl)-5-methyl-cyclopentanecarboxylic acidnepetalic acid	HMDB
2-Methyl-5-(1-oxopropan-2-yl)cyclopentane-1-carboxylate	Generator

Chemical Formula

C₁₀H₁₆O₃

Average Molecular Weight

184.2322

Monoisotopic Molecular Weight

184.109944378

IUPAC Name

2-methyl-5-(1-oxopropan-2-yl)cyclopentane-1-carboxylic acid

Traditional Name

2-methyl-5-(1-oxopropan-2-yl)cyclopentane-1-carboxylic acid

CAS Registry Number

21651-54-7

SMILES

CC(C=O)C1CCC(C)C1C(O)=O

InChI Identifier

InChI=1S/C10H16O3/c1-6-3-4-8(7(2)5-11)9(6)10(12)13/h5-9H,3-4H2,1-2H3,(H,12,13)

InChI Key

RGTMAXSVLBZNEL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036117)

Source

Endogenous

Endogenous (HMDB: HMDB0036117)

Plant

Plant (HMDB: HMDB0036117)

Animal

Animal (HMDB: HMDB0036117)

Exogenous

Food

Food (HMDB: HMDB0036117)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036117)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036117)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036117)

Lipid metabolism pathway (HMDB: HMDB0036117)

Cellular process

Cell signaling (HMDB: HMDB0036117)

Biochemical process

Lipid transport (HMDB: HMDB0036117)

Role

Biological role

Energy source (HMDB: HMDB0036117)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036117)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	73 - 75 °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	3.45 g/L	ALOGPS
logP	1.51	ALOGPS
logP	1.53	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.26 m³·mol⁻¹	ChemAxon
Polarizability	19.71 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]+	141.949	31661259
DarkChem	[M-H]-	135.747	31661259
DeepCCS	[M+H]+	139.411	30932474
DeepCCS	[M-H]-	135.583	30932474
DeepCCS	[M-2H]-	172.826	30932474
DeepCCS	[M+Na]+	148.365	30932474
AllCCS	[M+H]+	141.0	32859911
AllCCS	[M+H-H2O]+	137.0	32859911
AllCCS	[M+NH4]+	144.8	32859911
AllCCS	[M+Na]+	145.9	32859911
AllCCS	[M-H]-	142.8	32859911
AllCCS	[M+Na-2H]-	143.8	32859911
AllCCS	[M+HCOO]-	145.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.88 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3641 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.19 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1676.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	322.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	433.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	513.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	860.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	371.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1105.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	335.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	305.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	125.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1'R)-Nepetalic acid	CC(C=O)C1CCC(C)C1C(O)=O	2577.8	Standard polar	33892256
(1'R)-Nepetalic acid	CC(C=O)C1CCC(C)C1C(O)=O	1331.8	Standard non polar	33892256
(1'R)-Nepetalic acid	CC(C=O)C1CCC(C)C1C(O)=O	1512.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1'R)-Nepetalic acid,1TMS,isomer #1	CC(C=O)C1CCC(C)C1C(=O)O[Si](C)(C)C	1508.6	Semi standard non polar	33892256
(1'R)-Nepetalic acid,1TMS,isomer #2	CC(=CO[Si](C)(C)C)C1CCC(C)C1C(=O)O	1640.9	Semi standard non polar	33892256
(1'R)-Nepetalic acid,2TMS,isomer #1	CC(=CO[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	1675.0	Semi standard non polar	33892256
(1'R)-Nepetalic acid,2TMS,isomer #1	CC(=CO[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	1629.6	Standard non polar	33892256
(1'R)-Nepetalic acid,1TBDMS,isomer #1	CC(C=O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	1749.2	Semi standard non polar	33892256
(1'R)-Nepetalic acid,1TBDMS,isomer #2	CC(=CO[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	1875.3	Semi standard non polar	33892256
(1'R)-Nepetalic acid,2TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	2099.5	Semi standard non polar	33892256
(1'R)-Nepetalic acid,2TBDMS,isomer #1	CC(=CO[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	2066.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (1'R)-Nepetalic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kdm-9400000000-4e6a0b0376d1805c10ad	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1'R)-Nepetalic acid GC-MS (1 TMS) - 70eV, Positive	splash10-007c-9430000000-3e0dcc6f4178490fb06d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1'R)-Nepetalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1'R)-Nepetalic acid 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 - (1'R)-Nepetalic acid 10V, Positive-QTOF	splash10-00kr-0900000000-5e987da1c4c9928d0a74	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 20V, Positive-QTOF	splash10-05n0-4900000000-752a5d924b6443a0ef79	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 40V, Positive-QTOF	splash10-0kal-9100000000-a389ada76f03fc88d5cc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 10V, Positive-QTOF	splash10-00kr-0900000000-5e987da1c4c9928d0a74	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 20V, Positive-QTOF	splash10-05n0-4900000000-752a5d924b6443a0ef79	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 40V, Positive-QTOF	splash10-0kal-9100000000-a389ada76f03fc88d5cc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 10V, Positive-QTOF	splash10-00kr-0900000000-5e987da1c4c9928d0a74	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 20V, Positive-QTOF	splash10-05n0-4900000000-752a5d924b6443a0ef79	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 40V, Positive-QTOF	splash10-0kal-9100000000-a389ada76f03fc88d5cc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 10V, Negative-QTOF	splash10-001i-0900000000-688da9a4ce3644a6f2a6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 20V, Negative-QTOF	splash10-0019-1900000000-eb43d900661eb7b0c079	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 40V, Negative-QTOF	splash10-0a59-9400000000-3bbfd73e47c1afc87130	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 10V, Negative-QTOF	splash10-001i-0900000000-688da9a4ce3644a6f2a6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 20V, Negative-QTOF	splash10-0019-1900000000-eb43d900661eb7b0c079	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 40V, Negative-QTOF	splash10-0a59-9400000000-3bbfd73e47c1afc87130	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 10V, Negative-QTOF	splash10-001i-0900000000-688da9a4ce3644a6f2a6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 20V, Negative-QTOF	splash10-0019-1900000000-eb43d900661eb7b0c079	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 40V, Negative-QTOF	splash10-0a59-9400000000-3bbfd73e47c1afc87130	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 10V, Negative-QTOF	splash10-017i-0900000000-9453472fd235954a139d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 20V, Negative-QTOF	splash10-0a4r-1900000000-e5ac59d6406b67a4c061	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 40V, Negative-QTOF	splash10-05o0-9600000000-2b81c15af3bdd4659649	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 10V, Positive-QTOF	splash10-06s9-1900000000-e926466009643ccdef40	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 20V, Positive-QTOF	splash10-053r-8900000000-3ff90db2b90c25217838	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1'R)-Nepetalic acid 40V, Positive-QTOF	splash10-055f-9100000000-fb7bac5e962c7ce43cc7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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

FDB014965

KNApSAcK ID

C00010641

Chemspider ID

19793566

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12313272

PDB ID

Not Available

ChEBI ID

173886

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

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 (1'R)-Nepetalic acid (HMDB0036117)

MOL for HMDB0036117 ((1'R)-Nepetalic acid)

3D MOL for HMDB0036117 ((1'R)-Nepetalic acid)

3D SDF for HMDB0036117 ((1'R)-Nepetalic acid)

3D-SDF for HMDB0036117 ((1'R)-Nepetalic acid)

PDB for HMDB0036117 ((1'R)-Nepetalic acid)

3D PDB for HMDB0036117 ((1'R)-Nepetalic acid)

SMILES for HMDB0036117 ((1'R)-Nepetalic acid)

INCHI for HMDB0036117 ((1'R)-Nepetalic acid)

Structure for HMDB0036117 ((1'R)-Nepetalic acid)

3D Structure for HMDB0036117 ((1'R)-Nepetalic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra