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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:28:19 UTC

Update Date

2021-09-26 23:07:03 UTC

HMDB ID

HMDB0253670

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isophorone diisocyanate

Description

Isophorone diisocyanate, also known as IPDI, belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOC#N or its hydrocarbyl derivatives RN=C=O. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). Isophorone diisocyanate is an extremely weak basic (essentially neutral) compound (based on its pKa). Isophorone diisocyanate is a potentially toxic compound. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isophorone diisocyanate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isophorone diisocyanate 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

HMDB0253670
     RDKit          3D
Isophorone diisocyanate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.6782   -2.0484   -0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2662   -0.8390   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -0.9333    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6111    0.4277   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7950    1.5453   -0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1883    2.7726   -0.8334 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2156    3.8465   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    4.8314    0.5826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6731    1.3470   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.0787   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3872   -0.4290   -1.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452   -0.2385    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112    0.1275    1.7837 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082   -0.1171    2.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -0.3450    3.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533   -1.0053    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829   -2.8767   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102   -1.8156   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7771   -2.4214   -1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    0.0900    1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5413   -1.4201    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798   -1.4625    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    0.3786   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6890    0.6697   -0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176    1.6231    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    1.7756    0.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658    1.9086   -1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152   -1.5181   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221   -0.0559   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240    0.1121   -2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -1.3090    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401    0.3733   -0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2877   -0.8590    1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -2.0564    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  2  0
 10 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 16 33  1  0
 16 34  1  0
M  END


  Mrv0541 02241204362D          

 16 16  0  0  0  0            999 V2000
    1.7111   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.1433    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    0.0000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1501    2.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623    2.9313    0.0000 O   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253670

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CC(CC(C)(CN=C=O)C1)N=C=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O2/c1-11(2)4-10(14-9-16)5-12(3,6-11)7-13-8-15/h10H,4-7H2,1-3H3

> <INCHI_KEY>
NIMLQBUJDJZYEJ-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O2

> <MOLECULAR_WEIGHT>
222.2835

> <EXACT_MASS>
222.13682783

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.73076451972792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.125969815666667

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.187944145188181

> <JCHEM_POLAR_SURFACE_AREA>
58.86

> <JCHEM_REFRACTIVITY>
59.25140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isophorone diisocyanate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253670
     RDKit          3D
Isophorone diisocyanate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.6782   -2.0484   -0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2662   -0.8390   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -0.9333    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6111    0.4277   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7950    1.5453   -0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1883    2.7726   -0.8334 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2156    3.8465   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    4.8314    0.5826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6731    1.3470   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.0787   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3872   -0.4290   -1.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452   -0.2385    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112    0.1275    1.7837 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082   -0.1171    2.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -0.3450    3.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533   -1.0053    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829   -2.8767   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102   -1.8156   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7771   -2.4214   -1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    0.0900    1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5413   -1.4201    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798   -1.4625    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    0.3786   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6890    0.6697   -0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176    1.6231    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    1.7756    0.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658    1.9086   -1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152   -1.5181   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221   -0.0559   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240    0.1121   -2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -1.3090    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401    0.3733   -0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2877   -0.8590    1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -2.0564    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  2  0
 10 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 16 33  1  0
 16 34  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  C   UNK     0       3.194  -1.447   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.184   0.267   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.797   4.937   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.280   5.204   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.236   5.472   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   13                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    7    2                                                       
CONECT   14    5   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0253670
HETATM    1  C1  UNL     1      -1.678  -2.048  -0.902  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.266  -0.839  -0.053  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.121  -0.933   1.215  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.611   0.428  -0.749  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.795   1.545  -0.156  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.188   2.773  -0.833  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.216   3.846  -0.123  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.451   4.831   0.583  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.673   1.347  -0.260  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.113  -0.079  -0.348  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.387  -0.429  -1.789  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.445  -0.238   0.387  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.311   0.127   1.784  1.00  0.00           N  
HETATM   14  C11 UNL     1       3.308  -0.117   2.532  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.040  -0.345   3.529  1.00  0.00           O  
HETATM   16  C12 UNL     1       0.153  -1.005   0.325  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.983  -2.877  -0.220  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.510  -1.816  -1.568  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.777  -2.421  -1.436  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.407   0.090   1.552  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.541  -1.420   2.020  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.080  -1.463   1.014  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.569   0.379  -1.847  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.689   0.670  -0.506  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.118   1.623   0.924  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.136   1.776   0.675  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.066   1.909  -1.120  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.415  -1.518  -1.970  1.00  0.00           H  
HETATM   29  H13 UNL     1       2.422  -0.056  -2.025  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.724   0.112  -2.500  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.766  -1.309   0.339  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.240   0.373  -0.056  1.00  0.00           H  
HETATM   33  H17 UNL     1       0.288  -0.859   1.434  1.00  0.00           H  
HETATM   34  H18 UNL     1       0.513  -2.056   0.147  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   16
CONECT    3   20   21   22
CONECT    4    5   23   24
CONECT    5    6    9   25
CONECT    6    7    7
CONECT    7    8    8
CONECT    9   10   26   27
CONECT   10   11   12   16
CONECT   11   28   29   30
CONECT   12   13   31   32
CONECT   13   14   14
CONECT   14   15   15
CONECT   16   33   34
END

HMDB0253670
     RDKit          3D
Isophorone diisocyanate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.6782   -2.0484   -0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2662   -0.8390   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -0.9333    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6111    0.4277   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7950    1.5453   -0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1883    2.7726   -0.8334 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2156    3.8465   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    4.8314    0.5826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6731    1.3470   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.0787   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3872   -0.4290   -1.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452   -0.2385    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112    0.1275    1.7837 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3082   -0.1171    2.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -0.3450    3.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533   -1.0053    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829   -2.8767   -0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102   -1.8156   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7771   -2.4214   -1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072    0.0900    1.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5413   -1.4201    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798   -1.4625    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693    0.3786   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6890    0.6697   -0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1176    1.6231    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    1.7756    0.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658    1.9086   -1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152   -1.5181   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221   -0.0559   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7240    0.1121   -2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -1.3090    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401    0.3733   -0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2877   -0.8590    1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -2.0564    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  2  0
 10 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 16 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate	ChEBI
IPDI	ChEBI
Isocyanic acid, methylene(3,5,5-trimethyl-3,1-cyclohexylene) ester	ChEBI
Isophorone diamine diisocyanate	ChEBI
3-Isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanic acid	Generator
Isocyanate, methylene(3,5,5-trimethyl-3,1-cyclohexylene) ester	Generator
Isophorone diamine diisocyanic acid	Generator
Isophorone diisocyanic acid	Generator

Chemical Formula

C₁₂H₁₈N₂O₂

Average Molecular Weight

222.2835

Monoisotopic Molecular Weight

222.13682783

IUPAC Name

5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane

Traditional Name

isophorone diisocyanate

CAS Registry Number

Not Available

SMILES

CC1(C)CC(CC(C)(CN=C=O)C1)N=C=O

InChI Identifier

InChI=1S/C12H18N2O2/c1-11(2)4-10(14-9-16)5-12(3,6-11)7-13-8-15/h10H,4-7H2,1-3H3

InChI Key

NIMLQBUJDJZYEJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOC#N or its hydrocarbyl derivatives RN=C=O.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Isocyanates

Direct Parent

Isocyanates

Alternative Parents

Substituents

Isocyanate
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

diisocyanate (CHEBI:53214 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0253670)

Source

Exogenous

Exogenous (PMID: 31557052)

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	2.41	ALOGPS
logP	2.13	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.25 m³·mol⁻¹	ChemAxon
Polarizability	23.73 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]+	151.033	30932474
DeepCCS	[M-H]-	148.675	30932474
DeepCCS	[M-2H]-	183.09	30932474
DeepCCS	[M+Na]+	158.835	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	149.2	32859911
AllCCS	[M+NH4]+	156.1	32859911
AllCCS	[M+Na]+	157.1	32859911
AllCCS	[M-H]-	154.9	32859911
AllCCS	[M+Na-2H]-	155.7	32859911
AllCCS	[M+HCOO]-	156.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.2536 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.53 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1902.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	379.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	159.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	540.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	711.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1072.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	401.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1393.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	347.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	344.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	314.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	16.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isophorone diisocyanate	CC1(C)CC(CC(C)(CN=C=O)C1)N=C=O	2308.7	Standard polar	33892256
Isophorone diisocyanate	CC1(C)CC(CC(C)(CN=C=O)C1)N=C=O	1455.2	Standard non polar	33892256
Isophorone diisocyanate	CC1(C)CC(CC(C)(CN=C=O)C1)N=C=O	1554.4	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 - Isophorone diisocyanate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-5910000000-c19afc76593fa47648d7	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isophorone diisocyanate 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 - Isophorone diisocyanate 10V, Positive-QTOF	splash10-00e9-0980000000-42c7c2fdf96137f312f0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 20V, Positive-QTOF	splash10-001i-0910000000-4bbecbf9713e6585a049	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 40V, Positive-QTOF	splash10-01x0-5900000000-4b64defed855560bd0a3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 10V, Negative-QTOF	splash10-00di-2190000000-0de30ae86d208722f0e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 20V, Negative-QTOF	splash10-006x-9250000000-6156d7e07d2bd9b7d94e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 40V, Negative-QTOF	splash10-0006-9000000000-1bb6b7de2c6d6e055362	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 10V, Positive-QTOF	splash10-0019-0900000000-432861dca6d6eb8c2889	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 20V, Positive-QTOF	splash10-074i-2900000000-aa9fcdf85289714eaa27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 40V, Positive-QTOF	splash10-05fr-4900000000-9320709b371f2ef9bbbd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 10V, Negative-QTOF	splash10-006x-2960000000-5b2662cf43d5eeb7882d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 20V, Negative-QTOF	splash10-0006-9600000000-fa1943750a1b1b783a5c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isophorone diisocyanate 40V, Negative-QTOF	splash10-0006-9000000000-51d283be4237ed8ab376	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

Isophorone_diisocyanate

METLIN ID

Not Available

PubChem Compound

169132

PDB ID

Not Available

ChEBI ID

53214

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 Isophorone diisocyanate (HMDB0253670)

MOL for HMDB0253670 (Isophorone diisocyanate)

3D MOL for HMDB0253670 (Isophorone diisocyanate)

3D SDF for HMDB0253670 (Isophorone diisocyanate)

3D-SDF for HMDB0253670 (Isophorone diisocyanate)

PDB for HMDB0253670 (Isophorone diisocyanate)

3D PDB for HMDB0253670 (Isophorone diisocyanate)

SMILES for HMDB0253670 (Isophorone diisocyanate)

INCHI for HMDB0253670 (Isophorone diisocyanate)

Structure for HMDB0253670 (Isophorone diisocyanate)

3D Structure for HMDB0253670 (Isophorone diisocyanate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra