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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:54:21 UTC

Update Date

2022-03-07 02:54:18 UTC

HMDB ID

HMDB0034971

Secondary Accession Numbers

HMDB34971

Metabolite Identification

Common Name

(1R,2R,3S,1'R)-Nepetalinic acid

Description

(1R,2R,3S,1'R)-Nepetalinic acid, also known as (1R,2R,3S,1'r)-nepetalinate, 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 (1R,2R,3S,1'R)-Nepetalinic acid.

Structure

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

HMDB0034971
     RDKit          3D
(1R,2R,3S,1'R)-Nepetalinic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    2.8134    1.0354    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9424    0.0677   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    0.7851   -1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151    1.2569   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548   -0.0346   -0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6513    0.2751    0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1670   -0.9672    1.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265    0.7778   -0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090    1.9363    0.0087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -0.0033   -1.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.3432    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076   -1.7656    1.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277   -2.1699    2.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015   -2.6771   -0.0150 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    1.8212    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143    1.5084   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3754    0.5109    1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -0.7843   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9674    1.6369   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    0.0572   -2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1939    1.9823    0.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636    1.6239   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279   -0.7776   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    0.9937    1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982   -0.7399    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578   -1.2087    2.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1526   -1.8588    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1783   -0.3384   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954    0.2945    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152   -2.8943   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
M  END


  Mrv0541 02241208362D          

 14 14  0  0  0  0            999 V2000
    0.7834    1.7733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9483   -1.7733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358    0.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608    0.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0208   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534   -1.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958   -0.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834    0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208    1.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034971

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O4/c1-5-3-4-7(6(2)9(11)12)8(5)10(13)14/h5-8H,3-4H2,1-2H3,(H,11,12)(H,13,14)

> <INCHI_KEY>
OIFCPZGZZQQDNO-UHFFFAOYSA-N

> <FORMULA>
C10H16O4

> <MOLECULAR_WEIGHT>
200.2316

> <EXACT_MASS>
200.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.25915889145364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1-carboxyethyl)-5-methylcyclopentane-1-carboxylic acid

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.6869392093333333

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.823431573682889

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.092871626175394

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
49.183

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(1-carboxyethyl)-5-methylcyclopentane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034971
     RDKit          3D
(1R,2R,3S,1'R)-Nepetalinic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    2.8134    1.0354    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9424    0.0677   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    0.7851   -1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151    1.2569   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548   -0.0346   -0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6513    0.2751    0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1670   -0.9672    1.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265    0.7778   -0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090    1.9363    0.0087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -0.0033   -1.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.3432    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076   -1.7656    1.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277   -2.1699    2.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015   -2.6771   -0.0150 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    1.8212    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143    1.5084   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3754    0.5109    1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -0.7843   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9674    1.6369   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    0.0572   -2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1939    1.9823    0.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636    1.6239   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279   -0.7776   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    0.9937    1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982   -0.7399    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578   -1.2087    2.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1526   -1.8588    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1783   -0.3384   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954    0.2945    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152   -2.8943   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.462   3.310   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.770  -3.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.692  -2.232   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.000  -0.692   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.078   0.538   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.000   1.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.540   1.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.540  -0.230   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.772  -1.154   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.846  -2.694   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.232  -0.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.462   0.538   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.232   1.924   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.772   1.924   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3                                                            
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8                                                            
CONECT   10    3                                                            
CONECT   11   12                                                            
CONECT   12    5   11   13                                                  
CONECT   13    1   12   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0034971
HETATM    1  C1  UNL     1       2.813   1.035   0.646  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.942   0.068  -0.154  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.351   0.785  -1.328  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.015   1.257  -0.767  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.455  -0.035  -0.116  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.651   0.275   0.743  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.167  -0.967   1.419  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.726   0.778  -0.151  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.209   1.936   0.009  1.00  0.00           O  
HETATM   10  O2  UNL     1      -3.213  -0.003  -1.162  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.775  -0.343   0.743  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.908  -1.766   1.025  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.028  -2.170   2.207  1.00  0.00           O  
HETATM   14  O4  UNL     1       0.901  -2.677  -0.015  1.00  0.00           O  
HETATM   15  H1  UNL     1       2.143   1.821   1.036  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.514   1.508  -0.082  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.375   0.511   1.427  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.578  -0.784  -0.423  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.967   1.637  -1.673  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.140   0.057  -2.123  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.194   1.982   0.061  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.664   1.624  -1.533  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.628  -0.778  -0.889  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.355   0.994   1.506  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.198  -0.740   1.785  1.00  0.00           H  
HETATM   26  H12 UNL     1      -1.558  -1.209   2.312  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.153  -1.859   0.753  1.00  0.00           H  
HETATM   28  H14 UNL     1      -4.178  -0.338  -1.178  1.00  0.00           H  
HETATM   29  H15 UNL     1       0.695   0.294   1.628  1.00  0.00           H  
HETATM   30  H16 UNL     1       1.815  -2.894  -0.418  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   11   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   11   23
CONECT    6    7    8   24
CONECT    7   25   26   27
CONECT    8    9    9   10
CONECT   10   28
CONECT   11   12   29
CONECT   12   13   13   14
CONECT   14   30
END

HMDB0034971
     RDKit          3D
(1R,2R,3S,1'R)-Nepetalinic acid
 30 30  0  0  0  0  0  0  0  0999 V2000
    2.8134    1.0354    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9424    0.0677   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    0.7851   -1.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151    1.2569   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548   -0.0346   -0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6513    0.2751    0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1670   -0.9672    1.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265    0.7778   -0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090    1.9363    0.0087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130   -0.0033   -1.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.3432    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076   -1.7656    1.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277   -2.1699    2.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015   -2.6771   -0.0150 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    1.8212    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143    1.5084   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3754    0.5109    1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -0.7843   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9674    1.6369   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    0.0572   -2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1939    1.9823    0.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636    1.6239   -1.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6279   -0.7776   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    0.9937    1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982   -0.7399    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5578   -1.2087    2.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1526   -1.8588    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1783   -0.3384   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954    0.2945    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152   -2.8943   -0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1R,2R,3S,1'r)-Nepetalinate	Generator
2-(1-Carboxyethyl)-5-methylcyclopentane-1-carboxylate	HMDB

Chemical Formula

C₁₀H₁₆O₄

Average Molecular Weight

200.2316

Monoisotopic Molecular Weight

200.104859

IUPAC Name

2-(1-carboxyethyl)-5-methylcyclopentane-1-carboxylic acid

Traditional Name

2-(1-carboxyethyl)-5-methylcyclopentane-1-carboxylic acid

CAS Registry Number

32603-11-5

SMILES

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

InChI Identifier

InChI=1S/C10H16O4/c1-5-3-4-7(6(2)9(11)12)8(5)10(13)14/h5-8H,3-4H2,1-2H3,(H,11,12)(H,13,14)

InChI Key

OIFCPZGZZQQDNO-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
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	85 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3233 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.69	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.18 m³·mol⁻¹	ChemAxon
Polarizability	20.26 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]+	145.533	31661259
DarkChem	[M-H]-	142.746	31661259
DeepCCS	[M+H]+	142.499	30932474
DeepCCS	[M-H]-	138.672	30932474
DeepCCS	[M-2H]-	176.238	30932474
DeepCCS	[M+Na]+	151.823	30932474
AllCCS	[M+H]+	144.3	32859911
AllCCS	[M+H-H2O]+	140.4	32859911
AllCCS	[M+NH4]+	147.9	32859911
AllCCS	[M+Na]+	149.0	32859911
AllCCS	[M-H]-	145.3	32859911
AllCCS	[M+Na-2H]-	146.1	32859911
AllCCS	[M+HCOO]-	147.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1R,2R,3S,1'R)-Nepetalinic acid	CC(C1CCC(C)C1C(O)=O)C(O)=O	2627.9	Standard polar	33892256
(1R,2R,3S,1'R)-Nepetalinic acid	CC(C1CCC(C)C1C(O)=O)C(O)=O	1495.8	Standard non polar	33892256
(1R,2R,3S,1'R)-Nepetalinic acid	CC(C1CCC(C)C1C(O)=O)C(O)=O	1667.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1R,2R,3S,1'R)-Nepetalinic acid,1TMS,isomer #1	CC1CCC(C(C)C(=O)O)C1C(=O)O[Si](C)(C)C	1643.4	Semi standard non polar	33892256
(1R,2R,3S,1'R)-Nepetalinic acid,1TMS,isomer #2	CC1CCC(C(C)C(=O)O[Si](C)(C)C)C1C(=O)O	1677.0	Semi standard non polar	33892256
(1R,2R,3S,1'R)-Nepetalinic acid,2TMS,isomer #1	CC1CCC(C(C)C(=O)O[Si](C)(C)C)C1C(=O)O[Si](C)(C)C	1685.4	Semi standard non polar	33892256
(1R,2R,3S,1'R)-Nepetalinic acid,1TBDMS,isomer #1	CC1CCC(C(C)C(=O)O)C1C(=O)O[Si](C)(C)C(C)(C)C	1896.7	Semi standard non polar	33892256
(1R,2R,3S,1'R)-Nepetalinic acid,1TBDMS,isomer #2	CC1CCC(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1C(=O)O	1925.7	Semi standard non polar	33892256
(1R,2R,3S,1'R)-Nepetalinic acid,2TBDMS,isomer #1	CC1CCC(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	2131.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pbc-9800000000-0f572492f0c92488312f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00bi-9362000000-7a98525d253a6a9ea4a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic 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 - (1R,2R,3S,1'R)-Nepetalinic acid 10V, Positive-QTOF	splash10-0zgi-0940000000-0e5748304e4a54e0224a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 20V, Positive-QTOF	splash10-0a59-2900000000-14ee6157af01f646837a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 40V, Positive-QTOF	splash10-0pb9-9300000000-c8df20d12196a9064d02	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 10V, Negative-QTOF	splash10-052b-0900000000-a673b2e575c19e7283d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 20V, Negative-QTOF	splash10-0a4i-0900000000-f67859ddd6e2ee21c6ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 40V, Negative-QTOF	splash10-0c0r-8900000000-aed64bb80becde8315a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 10V, Positive-QTOF	splash10-0pc9-0920000000-a54b278f57d03315107a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 20V, Positive-QTOF	splash10-0a4i-6900000000-cc290fc2938bb573ef9e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 40V, Positive-QTOF	splash10-066u-9000000000-0376933603017085c162	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 10V, Negative-QTOF	splash10-054k-1900000000-ac8cc608cbe2c7cc428e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 20V, Negative-QTOF	splash10-0bt9-0900000000-87f6863d6c4b9ae08c24	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 40V, Negative-QTOF	splash10-0560-9700000000-bbe82686eac1ebcda6f9	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

FDB013569

KNApSAcK ID

Not Available

Chemspider ID

35013806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560389

PDB ID

Not Available

ChEBI ID

172073

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1846711

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 (1R,2R,3S,1'R)-Nepetalinic acid (HMDB0034971)

MOL for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

3D MOL for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

3D SDF for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

3D-SDF for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

PDB for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

3D PDB for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

SMILES for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

INCHI for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

Structure for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

3D Structure for HMDB0034971 ((1R,2R,3S,1'R)-Nepetalinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra