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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:35:34 UTC

Update Date

2021-09-26 23:06:22 UTC

HMDB ID

HMDB0253250

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hydrogenated MDI

Description

Methylene bis(4-cyclohexylisocyanate), also known as dicyclohexylmethane 4,4'-diisocyanate or 4,4'-diisocyanatodicyclohexylmethane, 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 mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. 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). The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. It complexes with the ferric iron atom in this enzyme. Methylene bis(4-cyclohexylisocyanate) is an extremely weak basic (essentially neutral) compound (based on its pKa). Methylene bis(4-cyclohexylisocyanate) is a potentially toxic compound. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. 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. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hydrogenated mdi is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hydrogenated MDI 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

HMDB0253250
     RDKit          3D
Hydrogenated MDI
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.5927    0.6954   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.2505   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8449   -1.1217   -0.2197 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276   -0.9066    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4133    0.5770    0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113    0.9818    1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898    0.5790    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0863   -0.2030    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777   -0.6737   -0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1797   -1.4399    0.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1483   -0.5172    1.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9055    0.3672    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085    1.7695    0.7209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191    2.6624   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3328    3.4133   -1.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679    0.1219   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8775    0.4432   -0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962   -0.2125   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -1.4186   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318   -1.4873    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    1.1992   -0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445    0.7612    1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0031    2.0597    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097    0.4944    2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    1.4734   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345   -1.0590    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247    0.4710    1.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926   -1.3725   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747   -2.2447    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -1.9425    1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -1.1717    1.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    0.0399    2.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0125    0.1929    0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8994    0.7713   -1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5354   -0.9355   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081    0.5168   -1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    1.4004   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0653   -0.4795   -1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    0.4580   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -1.9260   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446   -2.0865    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  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  2  0
 14 15  2  0
 12 16  1  0
 16 17  1  0
  7 18  1  0
 18 19  1  0
 19  4  1  0
 17  9  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
M  END


  Mrv0541 02241204362D          

 19 20  0  0  0  0            999 V2000
    0.7145    0.4125    0.0000 O   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
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    2.8579   -2.4750    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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   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  2  2  0  0  0  0
  2  3  2  0  0  0  0
  3  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
  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253250

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C=NC1CCC(CC2CCC(CC2)N=C=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O2/c18-10-16-14-5-1-12(2-6-14)9-13-3-7-15(8-4-13)17-11-19/h12-15H,1-9H2

> <INCHI_KEY>
KORSJDCBLAPZEQ-UHFFFAOYSA-N

> <FORMULA>
C15H22N2O2

> <MOLECULAR_WEIGHT>
262.3474

> <EXACT_MASS>
262.168127958

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.909156236984764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-isocyanato-4-[(4-isocyanatocyclohexyl)methyl]cyclohexane

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
3.179045627666667

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.629190472628879

> <JCHEM_POLAR_SURFACE_AREA>
58.86

> <JCHEM_REFRACTIVITY>
71.39880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
HMDI

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253250
     RDKit          3D
Hydrogenated MDI
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.5927    0.6954   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.2505   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8449   -1.1217   -0.2197 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276   -0.9066    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4133    0.5770    0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113    0.9818    1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898    0.5790    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0863   -0.2030    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777   -0.6737   -0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1797   -1.4399    0.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1483   -0.5172    1.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9055    0.3672    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085    1.7695    0.7209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191    2.6624   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3328    3.4133   -1.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679    0.1219   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8775    0.4432   -0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962   -0.2125   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -1.4186   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318   -1.4873    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    1.1992   -0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445    0.7612    1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0031    2.0597    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097    0.4944    2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    1.4734   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345   -1.0590    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247    0.4710    1.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926   -1.3725   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747   -2.2447    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -1.9425    1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -1.1717    1.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    0.0399    2.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0125    0.1929    0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8994    0.7713   -1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5354   -0.9355   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081    0.5168   -1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    1.4004   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0653   -0.4795   -1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    0.4580   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -1.9260   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446   -2.0865    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  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  2  0
 14 15  2  0
 12 16  1  0
 16 17  1  0
  7 18  1  0
 18 19  1  0
 19  4  1  0
 17  9  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.334 -10.010   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334 -13.090   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    7   19                                                       
CONECT   19   18    4                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0253250
HETATM    1  O1  UNL     1       6.593   0.695  -0.162  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.768  -0.251  -0.124  1.00  0.00           C  
HETATM    3  N1  UNL     1       4.845  -1.122  -0.220  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.528  -0.907   0.379  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.413   0.577   0.655  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.011   0.982   1.034  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.990   0.579   0.003  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.086  -0.203   0.699  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.178  -0.674  -0.202  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.180  -1.440   0.637  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.148  -0.517   1.348  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.906   0.367   0.406  1.00  0.00           C  
HETATM   13  N2  UNL     1      -3.708   1.769   0.721  1.00  0.00           N  
HETATM   14  C11 UNL     1      -4.019   2.662  -0.132  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.333   3.413  -1.077  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.368   0.122  -0.993  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.877   0.443  -0.935  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.696  -0.212  -1.064  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.418  -1.419  -0.502  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.532  -1.487   1.325  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.856   1.199  -0.134  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.044   0.761   1.573  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.003   2.060   1.215  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.810   0.494   2.032  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.557   1.473  -0.491  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.335  -1.059   1.227  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.525   0.471   1.473  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.793  -1.372  -0.968  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.675  -2.245   0.091  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.589  -1.942   1.458  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.886  -1.172   1.857  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.605   0.040   2.137  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.013   0.193   0.455  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.899   0.771  -1.701  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.535  -0.936  -1.220  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.508   0.517  -1.993  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.782   1.400  -0.413  1.00  0.00           H  
HETATM   38  H19 UNL     1       1.065  -0.480  -1.914  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.502   0.458  -1.470  1.00  0.00           H  
HETATM   40  H21 UNL     1       2.903  -1.926  -1.372  1.00  0.00           H  
HETATM   41  H22 UNL     1       1.745  -2.086   0.058  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3
CONECT    3    4
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8   18   25
CONECT    8    9   26   27
CONECT    9   10   17   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   16   33
CONECT   13   14   14
CONECT   14   15   15
CONECT   16   17   34   35
CONECT   17   36   37
CONECT   18   19   38   39
CONECT   19   40   41
END

HMDB0253250
     RDKit          3D
Hydrogenated MDI
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.5927    0.6954   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.2505   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8449   -1.1217   -0.2197 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276   -0.9066    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4133    0.5770    0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0113    0.9818    1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898    0.5790    0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0863   -0.2030    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777   -0.6737   -0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1797   -1.4399    0.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1483   -0.5172    1.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9055    0.3672    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085    1.7695    0.7209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191    2.6624   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3328    3.4133   -1.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679    0.1219   -0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8775    0.4432   -0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962   -0.2125   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4183   -1.4186   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318   -1.4873    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    1.1992   -0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0445    0.7612    1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0031    2.0597    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097    0.4944    2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568    1.4734   -0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345   -1.0590    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247    0.4710    1.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926   -1.3725   -0.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747   -2.2447    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -1.9425    1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -1.1717    1.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    0.0399    2.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0125    0.1929    0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8994    0.7713   -1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5354   -0.9355   -1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081    0.5168   -1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    1.4004   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0653   -0.4795   -1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    0.4580   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -1.9260   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446   -2.0865    0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  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  2  0
 14 15  2  0
 12 16  1  0
 16 17  1  0
  7 18  1  0
 18 19  1  0
 19  4  1  0
 17  9  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-Diisocyanatodicyclohexylmethane	ChEBI
4,4'-Methylenedi(cyclohexyl isocyanate)	ChEBI
Bis(4-isocyanatocyclohexyl)methane	ChEBI
Dicyclohexylmethane 4,4'-diisocyanate	ChEBI
Dicyclohexylmethane-4,4'-di-isocyanate	ChEBI
HMDI	ChEBI
Hydrogenated mdi	ChEBI
Hylene W	ChEBI
Isocyanic acid, methylenedi-4,1-cyclohexylene ester	ChEBI
Methylene bis-(4-cyclohexylisocyanate)	ChEBI
4,4'-Methylenedi(cyclohexyl isocyanic acid)	Generator
Dicyclohexylmethane 4,4'-diisocyanic acid	Generator
Dicyclohexylmethane-4,4'-di-isocyanic acid	Generator
Isocyanate, methylenedi-4,1-cyclohexylene ester	Generator
Methylene bis-(4-cyclohexylisocyanic acid)	Generator
Methylene bis(4-cyclohexylisocyanic acid)	Generator
Methylene bis(4-cyclohexylisocyanate), (trans-trans)-isomer	MeSH
Dicyclohexylmethane-4,4'-diisocyanate	MeSH
HMDI CPD	MeSH
4,4-Methylene biscyclohexyl diisocyanate	MeSH

Chemical Formula

C₁₅H₂₂N₂O₂

Average Molecular Weight

262.3474

Monoisotopic Molecular Weight

262.168127958

IUPAC Name

1-isocyanato-4-[(4-isocyanatocyclohexyl)methyl]cyclohexane

Traditional Name

HMDI

CAS Registry Number

Not Available

SMILES

O=C=NC1CCC(CC2CCC(CC2)N=C=O)CC1

InChI Identifier

InChI=1S/C15H22N2O2/c18-10-16-14-5-1-12(2-6-14)9-13-3-7-15(8-4-13)17-11-19/h12-15H,1-9H2

InChI Key

KORSJDCBLAPZEQ-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:53216 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	3.98	ALOGPS
logP	3.18	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-3.6	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	4	ChemAxon
Refractivity	71.4 m³·mol⁻¹	ChemAxon
Polarizability	29.91 Å³	ChemAxon
Number of Rings	2	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]+	163.957	30932474
DeepCCS	[M-H]-	161.599	30932474
DeepCCS	[M-2H]-	194.643	30932474
DeepCCS	[M+Na]+	170.05	30932474
AllCCS	[M+H]+	164.5	32859911
AllCCS	[M+H-H2O]+	161.2	32859911
AllCCS	[M+NH4]+	167.6	32859911
AllCCS	[M+Na]+	168.5	32859911
AllCCS	[M-H]-	169.4	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	169.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.7396 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.7 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2463.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	482.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	199.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	243.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	485.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	662.3 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	829.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	131.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1407.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	474.3 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	1542.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	409.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	380.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	306.7 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	56.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydrogenated MDI	O=C=NC1CCC(CC2CCC(CC2)N=C=O)CC1	2909.7	Standard polar	33892256
Hydrogenated MDI	O=C=NC1CCC(CC2CCC(CC2)N=C=O)CC1	2321.4	Standard non polar	33892256
Hydrogenated MDI	O=C=NC1CCC(CC2CCC(CC2)N=C=O)CC1	2165.0	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 - Hydrogenated MDI GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-2920000000-0c94def34397a34f48d3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydrogenated MDI 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 - Hydrogenated MDI 10V, Positive-QTOF	splash10-03di-0190000000-534aa45a1d066610b6ce	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 20V, Positive-QTOF	splash10-03k9-2960000000-71c522e2d1c1daec9499	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 40V, Positive-QTOF	splash10-0036-9820000000-adca25992b6ad9ad91d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 10V, Negative-QTOF	splash10-03di-0090000000-45f460f14583b9f39337	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 20V, Negative-QTOF	splash10-03di-3090000000-ce3cf414e55d5e272e72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 40V, Negative-QTOF	splash10-0006-9000000000-5967e7479c7390704b67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 10V, Positive-QTOF	splash10-02g9-0190000000-1791c7a112d2dfae44df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 20V, Positive-QTOF	splash10-000i-1390000000-28c5b8c1166209bd5396	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 40V, Positive-QTOF	splash10-00c3-4930000000-ac3d778288cb80824323	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 10V, Negative-QTOF	splash10-01q9-0090000000-3da56d4bf3a0a0bdcd0f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 20V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrogenated MDI 40V, Negative-QTOF	splash10-0006-9210000000-3039fb3457d68fe3b19f	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

Not Available

METLIN ID

Not Available

PubChem Compound

21202

PDB ID

Not Available

ChEBI ID

53216

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 Hydrogenated MDI (HMDB0253250)

MOL for HMDB0253250 (Hydrogenated MDI)

3D MOL for HMDB0253250 (Hydrogenated MDI)

3D SDF for HMDB0253250 (Hydrogenated MDI)

3D-SDF for HMDB0253250 (Hydrogenated MDI)

PDB for HMDB0253250 (Hydrogenated MDI)

3D PDB for HMDB0253250 (Hydrogenated MDI)

SMILES for HMDB0253250 (Hydrogenated MDI)

INCHI for HMDB0253250 (Hydrogenated MDI)

Structure for HMDB0253250 (Hydrogenated MDI)

3D Structure for HMDB0253250 (Hydrogenated MDI)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra