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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:52:57 UTC

Update Date

2022-11-23 22:29:19 UTC

HMDB ID

HMDB0257162

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Resmethrin

Description

Resmethrin, also known as durekyl or ectokyl, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on Resmethrin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Resmethrin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Resmethrin 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

HMDB0257162
     RDKit          3D
resmethrin
 51 53  0  0  0  0  0  0  0  0999 V2000
   -4.6519   -1.6475    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6987   -1.8609   -0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4232   -3.0421   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1177   -1.0338   -0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    0.1800   -0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    0.8911   -1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    1.4140   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9887    1.8726    0.0364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    1.3999   -1.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    1.8616   -1.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8483    1.1657   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672    1.5823    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.6936    1.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743   -0.2736    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7721   -1.4402    1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2241   -1.1558    1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311   -0.5879    2.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1814   -0.3047    2.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9084   -0.5921    1.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2874   -1.1568   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9467   -1.4368   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.0282   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7459    1.5260   -0.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5787    2.6433    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8488    1.7903   -1.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7409   -2.0373    1.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7953   -0.5525    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5095   -2.1460    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2866   -3.9188   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4945   -2.8149   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9697   -3.3123   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1687   -1.2152   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9149    0.0664    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    0.5092   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031    1.6432   -2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180    2.9665   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    2.4543    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5369   -2.3330    0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5282   -1.6839    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2495   -0.3751    3.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7013    0.1354    3.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9639   -0.3868    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8692   -1.3760   -0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4457   -1.8751   -0.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7452   -0.6341   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593    2.2232    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    3.4358   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5801    3.0992    0.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448    0.8901   -2.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7560    2.2099   -1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4566    2.5679   -2.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14 22  2  0
  6 23  1  0
 23 24  1  0
 23 25  1  0
 23  5  1  0
 22 11  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
M  END


  Mrv1652307282022252D          

 25 27  0  0  0  0            999 V2000
    0.1050    5.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    7.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0289    7.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2929    7.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3931   -0.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2136   -0.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9082    0.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5491    0.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437    1.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5339    5.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3998    1.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1698    3.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    3.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5024    4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    6.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0642    1.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5024    3.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9149    2.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2484    6.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0734    6.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879    5.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6609    7.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5024    6.3712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0899    2.6267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879    5.1337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15 10  2  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 10  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22  3  1  0  0  0  0
 22  4  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 21  2  0  0  0  0
 24 13  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 25 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257162

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CC1C(C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3

> <INCHI_KEY>
VEMKTZHHVJILDY-UHFFFAOYSA-N

> <FORMULA>
C22H26O3

> <MOLECULAR_WEIGHT>
338.44

> <EXACT_MASS>
338.188194698

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.33859983119672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
5.067613150333332

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8523993908940475

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
99.8796

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
for-syn

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0257162
     RDKit          3D
resmethrin
 51 53  0  0  0  0  0  0  0  0999 V2000
   -4.6519   -1.6475    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6987   -1.8609   -0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4232   -3.0421   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1177   -1.0338   -0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    0.1800   -0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    0.8911   -1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    1.4140   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9887    1.8726    0.0364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    1.3999   -1.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    1.8616   -1.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8483    1.1657   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672    1.5823    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.6936    1.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743   -0.2736    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7721   -1.4402    1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2241   -1.1558    1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311   -0.5879    2.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1814   -0.3047    2.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9084   -0.5921    1.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2874   -1.1568   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9467   -1.4368   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.0282   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7459    1.5260   -0.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5787    2.6433    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8488    1.7903   -1.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7409   -2.0373    1.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7953   -0.5525    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5095   -2.1460    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2866   -3.9188   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4945   -2.8149   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9697   -3.3123   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1687   -1.2152   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9149    0.0664    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    0.5092   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031    1.6432   -2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180    2.9665   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    2.4543    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5369   -2.3330    0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5282   -1.6839    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2495   -0.3751    3.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7013    0.1354    3.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9639   -0.3868    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8692   -1.3760   -0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4457   -1.8751   -0.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7452   -0.6341   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593    2.2232    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    3.4358   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5801    3.0992    0.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448    0.8901   -2.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7560    2.2099   -1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4566    2.5679   -2.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14 22  2  0
  6 23  1  0
 23 24  1  0
 23 25  1  0
 23  5  1  0
 22 11  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
M  END

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0       0.196  11.123   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.530  13.433   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.787  14.217   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.147  14.217   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.200  -0.563   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.732  -0.402   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.295   0.683   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.358   1.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.922   2.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.863  11.123   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.080   3.657   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.650   6.368   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.158   6.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.404   8.813   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.530  11.893   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.453   2.250   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.404   7.273   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.174   4.903   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.197  11.893   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.737  11.893   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.071  11.123   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.967  13.227   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.404  11.893   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.634   4.903   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.071   9.583   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   22                                                            
CONECT    4   22                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   16                                                       
CONECT    9    7   16                                                       
CONECT   10   15   19                                                       
CONECT   11   16   18                                                       
CONECT   12   17   18                                                       
CONECT   13   17   24                                                       
CONECT   14   17   25                                                       
CONECT   15    1    2   10                                                  
CONECT   16    8    9   11                                                  
CONECT   17   12   13   14                                                  
CONECT   18   11   12   24                                                  
CONECT   19   10   20   22                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   23   25                                                  
CONECT   22    3    4   19   20                                             
CONECT   23   21                                                            
CONECT   24   13   18                                                       
CONECT   25   14   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0257162
HETATM    1  C1  UNL     1      -4.652  -1.648   1.306  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.699  -1.861  -0.161  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.423  -3.042  -0.696  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.118  -1.034  -0.987  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.366   0.180  -0.559  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.514   0.891  -1.542  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.168   1.414  -1.118  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.989   1.873   0.036  1.00  0.00           O  
HETATM    9  O2  UNL     1      -0.106   1.400  -1.987  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.200   1.862  -1.703  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.848   1.166  -0.593  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.867   1.582   0.716  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.549   0.694   1.431  1.00  0.00           O  
HETATM   14  C11 UNL     1       2.974  -0.274   0.672  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.772  -1.440   1.139  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.224  -1.156   1.066  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.831  -0.588   2.191  1.00  0.00           C  
HETATM   18  C15 UNL     1       7.181  -0.305   2.172  1.00  0.00           C  
HETATM   19  C16 UNL     1       7.908  -0.592   1.029  1.00  0.00           C  
HETATM   20  C17 UNL     1       7.287  -1.157  -0.079  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.947  -1.437  -0.057  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.563  -0.028  -0.612  1.00  0.00           C  
HETATM   23  C20 UNL     1      -3.746   1.526  -0.977  1.00  0.00           C  
HETATM   24  C21 UNL     1      -3.579   2.643   0.051  1.00  0.00           C  
HETATM   25  C22 UNL     1      -4.849   1.790  -1.968  1.00  0.00           C  
HETATM   26  H1  UNL     1      -3.741  -2.037   1.776  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.795  -0.553   1.527  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.509  -2.146   1.831  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.287  -3.919  -0.032  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.494  -2.815  -0.879  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.970  -3.312  -1.671  1.00  0.00           H  
HETATM   32  H7  UNL     1      -4.169  -1.215  -2.053  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.915   0.066   0.460  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.561   0.509  -2.582  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.803   1.643  -2.632  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.218   2.967  -1.610  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.437   2.454   1.174  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.537  -2.333   0.509  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.528  -1.684   2.187  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.249  -0.375   3.061  1.00  0.00           H  
HETATM   41  H16 UNL     1       7.701   0.135   3.016  1.00  0.00           H  
HETATM   42  H17 UNL     1       8.964  -0.387   0.973  1.00  0.00           H  
HETATM   43  H18 UNL     1       7.869  -1.376  -0.966  1.00  0.00           H  
HETATM   44  H19 UNL     1       5.446  -1.875  -0.907  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.745  -0.634  -1.496  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.259   2.223   1.028  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.906   3.436  -0.321  1.00  0.00           H  
HETATM   48  H23 UNL     1      -4.580   3.099   0.227  1.00  0.00           H  
HETATM   49  H24 UNL     1      -5.045   0.890  -2.589  1.00  0.00           H  
HETATM   50  H25 UNL     1      -5.756   2.210  -1.520  1.00  0.00           H  
HETATM   51  H26 UNL     1      -4.457   2.568  -2.682  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4    4
CONECT    3   29   30   31
CONECT    4    5   32
CONECT    5    6   23   33
CONECT    6    7   23   34
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   35   36
CONECT   11   12   12   22
CONECT   12   13   37
CONECT   13   14
CONECT   14   15   22   22
CONECT   15   16   38   39
CONECT   16   17   17   21
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   21   44
CONECT   22   45
CONECT   23   24   25
CONECT   24   46   47   48
CONECT   25   49   50   51
END

HMDB0257162
     RDKit          3D
resmethrin
 51 53  0  0  0  0  0  0  0  0999 V2000
   -4.6519   -1.6475    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6987   -1.8609   -0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4232   -3.0421   -0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1177   -1.0338   -0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    0.1800   -0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    0.8911   -1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    1.4140   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9887    1.8726    0.0364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    1.3999   -1.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    1.8616   -1.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8483    1.1657   -0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672    1.5823    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.6936    1.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743   -0.2736    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7721   -1.4402    1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2241   -1.1558    1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311   -0.5879    2.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1814   -0.3047    2.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9084   -0.5921    1.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2874   -1.1568   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9467   -1.4368   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -0.0282   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7459    1.5260   -0.9771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5787    2.6433    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8488    1.7903   -1.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7409   -2.0373    1.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7953   -0.5525    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5095   -2.1460    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2866   -3.9188   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4945   -2.8149   -0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9697   -3.3123   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1687   -1.2152   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9149    0.0664    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613    0.5092   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031    1.6432   -2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180    2.9665   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    2.4543    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5369   -2.3330    0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5282   -1.6839    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2495   -0.3751    3.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7013    0.1354    3.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9639   -0.3868    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8692   -1.3760   -0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4457   -1.8751   -0.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7452   -0.6341   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2593    2.2232    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    3.4358   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5801    3.0992    0.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448    0.8901   -2.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7560    2.2099   -1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4566    2.5679   -2.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14 22  2  0
  6 23  1  0
 23 24  1  0
 23 25  1  0
 23  5  1  0
 22 11  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5-(Phenylmethyl)-3-furanyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate	ChEBI
5-Benzyl-3-furylmethyl (+-)-cis,trans-chrysanthemate	ChEBI
5-Benzyl-3-furylmethyl (1Rs,3Rs;1Rs,3Sr)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate	ChEBI
Durekyl	Kegg
Ectokyl	Kegg
(5-(Phenylmethyl)-3-furanyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid	Generator
5-Benzyl-3-furylmethyl (+-)-cis,trans-chrysanthemic acid	Generator
5-Benzyl-3-furylmethyl (1Rs,3Rs;1Rs,3Sr)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid	Generator
(5-Benzyl-3-furyl)methyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropemecarboxylate	MeSH
Scourge	MeSH

Chemical Formula

C₂₂H₂₆O₃

Average Molecular Weight

338.44

Monoisotopic Molecular Weight

338.188194698

IUPAC Name

(5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

Traditional Name

for-syn

CAS Registry Number

Not Available

SMILES

CC(C)=CC1C(C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C

InChI Identifier

InChI=1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3

InChI Key

VEMKTZHHVJILDY-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Monocyclic monoterpenoid
Monocyclic benzene moiety
Cyclopropanecarboxylic acid or derivatives
Benzenoid
Heteroaromatic compound
Furan
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cyclopropanes (CHEBI:8811 )
furans (CHEBI:8811 )
Pyrethroid insecticides (C10991 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0257162)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

agrochemical (HMDB: HMDB0257162)

Agriculture

Pesticide

Insecticide

pyrethroid ester insecticide (HMDB: HMDB0257162)

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	5.38	ALOGPS
logP	5.07	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	99.88 m³·mol⁻¹	ChemAxon
Polarizability	38.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	187.512	30932474
DeepCCS	[M-H]-	185.154	30932474
DeepCCS	[M-2H]-	219.327	30932474
DeepCCS	[M+Na]+	194.679	30932474
AllCCS	[M+H]+	184.6	32859911
AllCCS	[M+H-H2O]+	181.6	32859911
AllCCS	[M+NH4]+	187.4	32859911
AllCCS	[M+Na]+	188.2	32859911
AllCCS	[M-H]-	190.0	32859911
AllCCS	[M+Na-2H]-	189.7	32859911
AllCCS	[M+HCOO]-	189.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
resmethrin	CC(C)=CC1C(C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C	2958.1	Standard polar	33892256
resmethrin	CC(C)=CC1C(C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C	2302.1	Standard non polar	33892256
resmethrin	CC(C)=CC1C(C(=O)OCC2=COC(CC3=CC=CC=C3)=C2)C1(C)C	2363.9	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 - Resmethrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-08-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Resmethrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dl-8900000000-c40ec51d53be4cbfb9d1	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resmethrin 30V, Positive-QTOF	splash10-00dl-2920000000-df032c0bc12bc76557a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resmethrin 15V, Positive-QTOF	splash10-0079-0429000000-10dc84a36c0b4b3c249f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resmethrin 45V, Positive-QTOF	splash10-0006-4900000000-bf183a6a22511c91d052	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resmethrin 60V, Positive-QTOF	splash10-0006-6900000000-5674fd24cdad4874ee16	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resmethrin 30V, Positive-QTOF	splash10-00dl-2920000000-755626dfa3e8e43acd4f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resmethrin 75V, Positive-QTOF	splash10-002f-8900000000-884e993eff83a90f18db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Resmethrin 90V, Positive-QTOF	splash10-002f-9700000000-e1997e6b5a9d9260999a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resmethrin 10V, Positive-QTOF	splash10-0079-0926000000-0fb918a4bbc4bee251b8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resmethrin 20V, Positive-QTOF	splash10-00di-1911000000-a86170594036d2641bee	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resmethrin 40V, Positive-QTOF	splash10-0l6r-4900000000-18c056037d5a7b1ebb5e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resmethrin 10V, Negative-QTOF	splash10-000i-0409000000-d88ffbc582501a319235	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resmethrin 20V, Negative-QTOF	splash10-01bj-0912000000-763c41ab2e9c3ea0e3ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Resmethrin 40V, Negative-QTOF	splash10-00rt-1900000000-16d53356f64b1d6c2c34	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

4877

KEGG Compound ID

C10991

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Resmethrin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

8811

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1331131

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 Resmethrin (HMDB0257162)

MOL for HMDB0257162 (Resmethrin)

3D MOL for HMDB0257162 (Resmethrin)

3D SDF for HMDB0257162 (Resmethrin)

3D-SDF for HMDB0257162 (Resmethrin)

PDB for HMDB0257162 (Resmethrin)

3D PDB for HMDB0257162 (Resmethrin)

SMILES for HMDB0257162 (Resmethrin)

INCHI for HMDB0257162 (Resmethrin)

Structure for HMDB0257162 (Resmethrin)

3D Structure for HMDB0257162 (Resmethrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra