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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:45:15 UTC

Update Date

2021-09-26 23:06:29 UTC

HMDB ID

HMDB0253340

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Icaridin

Description

Icaridin belongs to the class of organic compounds known as piperidinecarboxylic acids. Piperidinecarboxylic acids are compounds containing a piperidine ring which bears a carboxylic acid group. Icaridin is an extremely weak basic (essentially neutral) compound (based on its pKa). Icaridin is a potentially toxic compound. Consumer Reports retests in 2006 gave as result that a 7% solution of icaridin offered little or no protection against Aedes mosquitoes (vector of dengue fever) and a protection time of about 2.5 hours against Culex (vector of West Nile virus), while a 15% solution was good for about one hour against Aedes and 4.8 hours against Culex. It has broad efficacy against various insects and ticks and is almost colorless and odorless. The commercial material contains a mixture of all four stereoisomers. Icaridin contains two stereocenters: one where the hydroxyethyl chain attaches to the ring, and one where the sec-butyl attaches to the oxygen of the carbamate. The crystal structure of AgamOBP1•Icaridin complex (PDB: 5EL2) revealed that Icaridin binds to the DEET-binding site in two distinct orientationsand also to a second binding site (sIC-binding site) located at the C-terminal region of the AgamOBP1. A 2018 study found that icaridin, in what the authors described as conservative exposure doses, is highly toxic to salamander larvae. The name picaridin was proposed as an International Nonproprietary Name (INN) to the World Health Organization (WHO), but the official name that has been approved by the WHO is icaridin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Icaridin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Icaridin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253340
     RDKit          3D
Icaridin
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.3784    0.2172    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6181    0.7644    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828    0.1165   -0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125    0.6540   -2.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.1582   -0.3126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5649   -0.9573   -0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -2.0781   -0.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -0.8229    0.3577 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391   -2.0314    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9929   -1.8999    2.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -0.7356    2.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3455    0.5491    1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.4362    0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    0.8571   -0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    0.9795   -1.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895    1.3738   -3.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449   -0.5954    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0413    1.0328    2.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519   -0.1635    2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433    1.8567    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6583    0.5180   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -0.9741   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9410    0.3110   -2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    1.7499   -2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    0.1845   -2.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4328   -2.1217   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8941   -2.9375    0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -1.6974    2.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5344   -2.8089    2.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2825   -0.6091    3.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8504   -1.0184    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    1.2633    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981    0.9840    2.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416    1.2223    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0357    0.1632   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    1.8822   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010    0.0213   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877    1.7783   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231    2.3781   -3.0451 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
M  END

  Mrv0541 04251301022D          

 16 16  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253340

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)OC(=O)N1CCCCC1CCO

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO3/c1-3-10(2)16-12(15)13-8-5-4-6-11(13)7-9-14/h10-11,14H,3-9H2,1-2H3

> <INCHI_KEY>
QLHULAHOXSSASE-UHFFFAOYSA-N

> <FORMULA>
C12H23NO3

> <MOLECULAR_WEIGHT>
229.3159

> <EXACT_MASS>
229.167793607

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.160236513548416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
butan-2-yl 2-(2-hydroxyethyl)piperidine-1-carboxylate

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
1.6122512423333326

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.923174449744579

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3950034956817206

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
62.54420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
icaridin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253340
     RDKit          3D
Icaridin
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.3784    0.2172    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6181    0.7644    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828    0.1165   -0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125    0.6540   -2.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.1582   -0.3126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5649   -0.9573   -0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -2.0781   -0.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -0.8229    0.3577 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391   -2.0314    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9929   -1.8999    2.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -0.7356    2.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3455    0.5491    1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.4362    0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    0.8571   -0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    0.9795   -1.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895    1.3738   -3.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449   -0.5954    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0413    1.0328    2.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519   -0.1635    2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433    1.8567    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6583    0.5180   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -0.9741   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9410    0.3110   -2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    1.7499   -2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    0.1845   -2.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4328   -2.1217   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8941   -2.9375    0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -1.6974    2.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5344   -2.8089    2.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2825   -0.6091    3.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8504   -1.0184    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    1.2633    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981    0.9840    2.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416    1.2223    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0357    0.1632   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    1.8822   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010    0.0213   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877    1.7783   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231    2.3781   -3.0451 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
M  END

HEADER    PROTEIN                                 25-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-13         0                                  
HETATM    1  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0253340
HETATM    1  C1  UNL     1       3.378   0.217   1.660  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.618   0.764   0.272  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.683   0.116  -0.708  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.912   0.654  -2.095  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.338   0.158  -0.313  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.565  -0.957  -0.037  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.123  -2.078  -0.153  1.00  0.00           O  
HETATM    8  N1  UNL     1      -0.791  -0.823   0.358  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.539  -2.031   0.630  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.993  -1.900   2.092  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.955  -0.736   2.125  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.346   0.549   1.683  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.442   0.436   0.496  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.226   0.857  -0.727  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.340   0.979  -1.948  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.189   1.374  -3.004  1.00  0.00           O  
HETATM   17  H1  UNL     1       2.645  -0.595   1.606  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.041   1.033   2.348  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.352  -0.164   2.062  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.543   1.857   0.310  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.658   0.518  -0.066  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.968  -0.974  -0.746  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.941   0.311  -2.403  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.910   1.750  -2.136  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.207   0.184  -2.811  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.433  -2.122  -0.015  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.894  -2.938   0.606  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.097  -1.697   2.691  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.534  -2.809   2.357  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.282  -0.609   3.186  1.00  0.00           H  
HETATM   31  H15 UNL     1      -3.850  -1.018   1.539  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.171   1.263   1.463  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.798   0.984   2.550  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.642   1.222   0.626  1.00  0.00           H  
HETATM   35  H19 UNL     1      -3.036   0.163  -0.983  1.00  0.00           H  
HETATM   36  H20 UNL     1      -2.613   1.882  -0.507  1.00  0.00           H  
HETATM   37  H21 UNL     1      -0.901   0.021  -2.257  1.00  0.00           H  
HETATM   38  H22 UNL     1      -0.588   1.778  -1.836  1.00  0.00           H  
HETATM   39  H23 UNL     1      -2.223   2.378  -3.045  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4    5   22
CONECT    4   23   24   25
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   13
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   34
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   39
END

HMDB0253340
     RDKit          3D
Icaridin
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.3784    0.2172    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6181    0.7644    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6828    0.1165   -0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125    0.6540   -2.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.1582   -0.3126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5649   -0.9573   -0.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -2.0781   -0.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -0.8229    0.3577 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391   -2.0314    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9929   -1.8999    2.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548   -0.7356    2.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3455    0.5491    1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.4362    0.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    0.8571   -0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    0.9795   -1.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895    1.3738   -3.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449   -0.5954    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0413    1.0328    2.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519   -0.1635    2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5433    1.8567    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6583    0.5180   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -0.9741   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9410    0.3110   -2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    1.7499   -2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    0.1845   -2.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4328   -2.1217   -0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8941   -2.9375    0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -1.6974    2.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5344   -2.8089    2.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2825   -0.6091    3.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8504   -1.0184    1.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    1.2633    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981    0.9840    2.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416    1.2223    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0357    0.1632   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    1.8822   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010    0.0213   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877    1.7783   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231    2.3781   -3.0451 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bayrepel	MeSH
Sec-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate	MeSH
2-(2-Hydroxyethyl)-1-piperidinecarboxylic acid 1-methylpropyl ester	MeSH
Saltidin	MeSH
Picaridin	MeSH
1-(1-Methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine	MeSH

Chemical Formula

C₁₂H₂₃NO₃

Average Molecular Weight

229.3159

Monoisotopic Molecular Weight

229.167793607

IUPAC Name

butan-2-yl 2-(2-hydroxyethyl)piperidine-1-carboxylate

Traditional Name

icaridin

CAS Registry Number

Not Available

SMILES

CCC(C)OC(=O)N1CCCCC1CCO

InChI Identifier

InChI=1S/C12H23NO3/c1-3-10(2)16-12(15)13-8-5-4-6-11(13)7-9-14/h10-11,14H,3-9H2,1-2H3

InChI Key

QLHULAHOXSSASE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidinecarboxylic acids. Piperidinecarboxylic acids are compounds containing a piperidine ring which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinecarboxylic acids and derivatives

Direct Parent

Piperidinecarboxylic acids

Alternative Parents

Substituents

Piperidinecarboxylic acid
Carbamic acid ester
Carbonic acid derivative
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0253340)
Extracellular (HMDB: HMDB0253340)

Source

Exogenous

Exogenous (HMDB: HMDB0253340)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	2.19	ALOGPS
logP	1.61	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	15.92	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.54 m³·mol⁻¹	ChemAxon
Polarizability	26.16 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
DeepCCS	[M+H]+	158.471	30932474
DeepCCS	[M-H]-	155.501	30932474
DeepCCS	[M-2H]-	191.795	30932474
DeepCCS	[M+Na]+	167.333	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	152.0	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	160.0	32859911
AllCCS	[M-H]-	158.1	32859911
AllCCS	[M+Na-2H]-	158.8	32859911
AllCCS	[M+HCOO]-	159.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Icaridin	CCC(C)OC(=O)N1CCCCC1CCO	2526.1	Standard polar	33892256
Icaridin	CCC(C)OC(=O)N1CCCCC1CCO	1727.5	Standard non polar	33892256
Icaridin	CCC(C)OC(=O)N1CCCCC1CCO	1706.0	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 - Icaridin GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9710000000-df0e7cebfacfe49cb92b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Icaridin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Icaridin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Icaridin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 55V, Positive-QTOF	splash10-001i-0900000000-58f1702d6f45aa777f96	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 40V, Positive-QTOF	splash10-001i-0900000000-5cef5dc711524ef3bd7f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 30V, Positive-QTOF	splash10-001i-0900000000-4038f3c5e4bfdaf32538	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 35V, Positive-QTOF	splash10-001i-0900000000-84fc35113c0426313f33	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 10V, Positive-QTOF	splash10-001i-0920000000-12396b24426a71c38be1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 20V, Positive-QTOF	splash10-001i-0900000000-53f3c51c337bee23b64f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 35V, Positive-QTOF	splash10-001i-0900000000-4f5cb36e92522cf58afa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 15V, Positive-QTOF	splash10-001i-0900000000-0b9182859c214da7e606	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 50V, Positive-QTOF	splash10-00o0-0900000000-a1a14503fdf7d842458f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 30V, Positive-QTOF	splash10-001i-0900000000-8c17f06df0e54407dca0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 45V, Positive-QTOF	splash10-001i-1900000000-c043d43ea90c7dc975c2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 55V, Positive-QTOF	splash10-001i-0900000000-46e5423e2b1f9aa6a625	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 50V, Positive-QTOF	splash10-00o0-0900000000-d86d9c4b63234864b6ec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 90V, Positive-QTOF	splash10-06e9-9100000000-d5e323bf9496a7bab621	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 80V, Positive-QTOF	splash10-001j-5900000000-4a68dbf94a50d9208492	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 35V, Positive-QTOF	splash10-001i-0900000000-0d4e859962f2ef377815	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 75V, Positive-QTOF	splash10-00si-9300000000-10e25ab0bf74159a2466	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Icaridin 60V, Positive-QTOF	splash10-001i-7900000000-f37268309c628ceaa722	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Icaridin 10V, Positive-QTOF	splash10-06si-2950000000-36505610e4aa874d91b4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Icaridin 20V, Positive-QTOF	splash10-0a4i-8900000000-930b890acdb962fdc88e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Icaridin 40V, Positive-QTOF	splash10-0bt9-9500000000-7fa289c2d7a8debee429	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Icaridin 10V, Negative-QTOF	splash10-004i-5980000000-61c3a48aef046b0e5a2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Icaridin 20V, Negative-QTOF	splash10-0fmj-5920000000-7b1cb290f7bcb281d48a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Icaridin 40V, Negative-QTOF	splash10-0kkc-8900000000-d8eedf690c9700bcb6e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Icaridin 10V, Positive-QTOF	splash10-001i-1890000000-683315a61d2715077005	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Icaridin

METLIN ID

Not Available

PubChem Compound

125098

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Icaridin (HMDB0253340)

MOL for HMDB0253340 (Icaridin)

3D MOL for HMDB0253340 (Icaridin)

3D SDF for HMDB0253340 (Icaridin)

3D-SDF for HMDB0253340 (Icaridin)

PDB for HMDB0253340 (Icaridin)

3D PDB for HMDB0253340 (Icaridin)

SMILES for HMDB0253340 (Icaridin)

INCHI for HMDB0253340 (Icaridin)

Structure for HMDB0253340 (Icaridin)

3D Structure for HMDB0253340 (Icaridin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra