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Showing NP-Card for N-Cyclohexylformamide (NP0002824)

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Record Information
Version1.0
Created at2020-11-23 19:41:21 UTC
Updated at2021-08-12 19:52:15 UTC
NP-MRD IDNP0002824
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Cyclohexylformamide
Provided ByBMRBBMRB logo
DescriptionN-Cyclohexylformamide, also known as formamidocyclohexane or N-formylcyclohexylamine, belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl). N-Cyclohexylformamide exists in all living organisms, ranging from bacteria to humans. N-Cyclohexylformamide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. N-Cyclohexylformamide is found in Mus musculus and Vitis vinifera. It was first documented in 1997 (PMID: 9132002). Based on a literature review a small amount of articles have been published on N-Cyclohexylformamide (PMID: 17984079) (PMID: 11882632) (PMID: 20733993) (PMID: 9760265).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002824 (N-Cyclohexylformamide)


     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   -3.4205   -1.6240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3609   -0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0330    0.5725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -0.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1962    1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902    1.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2079    0.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6393   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1529   -1.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6291    0.6758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141    1.5533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7740   -1.3384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.4845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1366    2.6583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8336    2.7899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    2.0588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2170    1.2844    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761   -0.6265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1050   -1.5325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5796   -2.7123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6095   -2.8438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749   -2.1128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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  4  1  0
  2 10  1  0
  3 11  1  0
  4 12  1  6
  5 13  1  6
  5 14  1  0
  6 15  1  6
  6 16  1  0
  7 17  1  6
  7 18  1  0
  8 19  1  6
  8 20  1  0
  9 21  1  1
  9 22  1  0
M  END
Download

3D MOL for NP0002824 (N-Cyclohexylformamide)

NP0002824
     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    3.2664   -0.6718    1.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858    0.0199    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9372    0.3497   -0.4873 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290   -0.1057    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0109    1.1432    0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    0.6531    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530    0.2019    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -1.0348   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -0.9183   -0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889    0.3654   -0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    0.9120   -1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -0.6997    1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296    1.7488   -0.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6861    1.6378    1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    1.4045    1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139   -0.2907    1.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1526   -0.0029    0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249    1.0536   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -1.3696   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6513   -1.8435    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0111   -0.5898   -1.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -1.9630   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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  4  1  0
  2 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
M  END
Download

3D SDF for NP0002824 (N-Cyclohexylformamide)


     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   -3.4205   -1.6240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3609   -0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0330    0.5725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -0.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1962    1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902    1.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2079    0.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6393   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1529   -1.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6291    0.6758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141    1.5533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7740   -1.3384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.4845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1366    2.6583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8336    2.7899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    2.0588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2170    1.2844    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761   -0.6265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1050   -1.5325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5796   -2.7123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6095   -2.8438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749   -2.1128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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  4  1  0
  2 10  1  0
  3 11  1  0
  4 12  1  6
  5 13  1  6
  5 14  1  0
  6 15  1  6
  6 16  1  0
  7 17  1  6
  7 18  1  0
  8 19  1  6
  8 20  1  0
  9 21  1  1
  9 22  1  0
M  END
> <DATABASE_ID>
NP0002824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=CNC1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO/c9-6-8-7-4-2-1-3-5-7/h6-7H,1-5H2,(H,8,9)

> <INCHI_KEY>
SWGXDLRCJNEEGZ-UHFFFAOYSA-N

> <FORMULA>
C7H13NO

> <MOLECULAR_WEIGHT>
127.1842

> <EXACT_MASS>
127.099714043

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.436237626750293

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-cyclohexylformamide

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
0.9439595613333335

> <ALOGPS_LOGS>
-0.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.447375199051702

> <JCHEM_PKA_STRONGEST_BASIC>
0.09265071582334106

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
35.8863

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclohexylformamide

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002824 (N-Cyclohexylformamide)

NP0002824
     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    3.2664   -0.6718    1.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858    0.0199    0.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9372    0.3497   -0.4873 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290   -0.1057    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0109    1.1432    0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2712    0.6531    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530    0.2019    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340   -1.0348   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -0.9183   -0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889    0.3654   -0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    0.9120   -1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -0.6997    1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2296    1.7488   -0.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6861    1.6378    1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    1.4045    1.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139   -0.2907    1.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1526   -0.0029    0.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249    1.0536   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -1.3696   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6513   -1.8435    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0111   -0.5898   -1.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -1.9630   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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  4  1  0
  2 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
M  END
Download

PDB for NP0002824 (N-Cyclohexylformamide)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0002824 (N-Cyclohexylformamide)

COMPND    NP0002824
HETATM    1  O1  UNL     1       3.266  -0.672   1.134  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.186   0.020   0.075  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.937   0.350  -0.487  1.00  0.00           N  
HETATM    4  C2  UNL     1       0.729  -0.106   0.150  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.011   1.143   0.649  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.271   0.653   1.307  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.153   0.202   0.134  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.534  -1.035  -0.425  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.100  -0.918  -0.784  1.00  0.00           C  
HETATM   10  H1  UNL     1       4.089   0.365  -0.409  1.00  0.00           H  
HETATM   11  H2  UNL     1       1.866   0.912  -1.348  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.961  -0.700   1.067  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.230   1.749  -0.256  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.686   1.638   1.347  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.750   1.404   1.925  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.014  -0.291   1.849  1.00  0.00           H  
HETATM   17  H8  UNL     1      -3.153  -0.003   0.508  1.00  0.00           H  
HETATM   18  H9  UNL     1      -2.125   1.054  -0.586  1.00  0.00           H  
HETATM   19  H10 UNL     1      -2.095  -1.370  -1.325  1.00  0.00           H  
HETATM   20  H11 UNL     1      -1.651  -1.843   0.330  1.00  0.00           H  
HETATM   21  H12 UNL     1       0.011  -0.590  -1.853  1.00  0.00           H  
HETATM   22  H13 UNL     1       0.333  -1.963  -0.780  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   11
CONECT    4    5    9   12
CONECT    5    6   13   14
CONECT    6    7   15   16
CONECT    7    8   17   18
CONECT    8    9   19   20
CONECT    9   21   22
END
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SMILES for NP0002824 (N-Cyclohexylformamide)

O=CNC1CCCCC1
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INCHI for NP0002824 (N-Cyclohexylformamide)

InChI=1S/C7H13NO/c9-6-8-7-4-2-1-3-5-7/h6-7H,1-5H2,(H,8,9)
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View in JSmol
Synonyms
ValueSource
CYCLOHEXYLFORMAMIDEChEBI
FormamidocyclohexaneChEBI
N-CyclohexylformamidChEBI
N-FormylcyclohexylamineChEBI
N-ZyklohexylformamidChEBI
Chemical FormulaC7H13NO
Average Mass127.1842 Da
Monoisotopic Mass127.09971 Da
IUPAC NameN-cyclohexylformamide
Traditional Namecyclohexylformamide
CAS Registry NumberNot Available
SMILES
O=CNC1CCCCC1
InChI Identifier
InChI=1S/C7H13NO/c9-6-8-7-4-2-1-3-5-7/h6-7H,1-5H2,(H,8,9)
InChI KeySWGXDLRCJNEEGZ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mus musculusLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentSecondary carboxylic acid amides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.23ALOGPS
logP0.94ChemAxon
logS-0.83ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)0.093ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.89 m³·mol⁻¹ChemAxon
Polarizability14.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0255105
DrugBank IDDB03559
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID12476
KEGG Compound IDC11519
BioCyc IDN-CYCLOHEXYLFORMAMIDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13017
PDB IDNot Available
ChEBI ID17945
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Imig JD, Zhao X, Capdevila JH, Morisseau C, Hammock BD: Soluble epoxide hydrolase inhibition lowers arterial blood pressure in angiotensin II hypertension. Hypertension. 2002 Feb;39(2 Pt 2):690-4. doi: 10.1161/hy0202.103788. [PubMed:11882632 ]
  3. Guliashvili T, Tibbelin J, Ryu J, Ottosson H: Unsuccessful attempts to add alcohols to transient 2-amino-2-siloxy-silenes - leading to a new benign route for base-free alcohol protection. Dalton Trans. 2010 Oct 21;39(39):9379-85. doi: 10.1039/c0dt00323a. Epub 2010 Aug 24. [PubMed:20733993 ]
  4. Ramaswamy S, Scholze M, Plapp BV: Binding of formamides to liver alcohol dehydrogenase. Biochemistry. 1997 Mar 25;36(12):3522-7. doi: 10.1021/bi962491z. [PubMed:9132002 ]
  5. Deng H, Schindler JF, Berst KB, Plapp BV, Callender R: A Raman spectroscopic characterization of bonding in the complex of horse liver alcohol dehydrogenase with NADH and N-cyclohexylformamide. Biochemistry. 1998 Oct 6;37(40):14267-78. doi: 10.1021/bi981477e. [PubMed:9760265 ]