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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:35:19 UTC

Update Date

2021-09-26 23:03:08 UTC

HMDB ID

HMDB0251256

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Difenoxin

Description

Difenoxin, also known as diphenoxilic acid or diphenoxilate, belongs to the class of organic compounds known as diphenylacetonitriles. These are cyclic aromatic compounds containing a diphenylacetonitrile moiety, which consists of a diphenylmethane linked to and acetonitrile to form 2,2-diphenylacetonitrile. Based on a literature review very few articles have been published on Difenoxin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Difenoxin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Difenoxin 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

1501
  Mrv0541 02231215312D          

 32 35  0  0  0  0            999 V2000
    3.6020    2.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704    3.6842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    0.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -1.5553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    2.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716    2.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3283    3.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469    2.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -2.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9603    4.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8788    2.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7356    3.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -4.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 13  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 21  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  5 13  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 14  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 21  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 23  2  0  0  0  0
 17 25  1  0  0  0  0
 18 24  2  0  0  0  0
 18 26  1  0  0  0  0
 19 22  2  0  0  0  0
 20 22  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 25 29  2  0  0  0  0
 26 30  2  0  0  0  0
 27 31  2  0  0  0  0
 28 32  2  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END

HMDB0251256
     RDKit          3D
Difenoxin
 60 63  0  0  0  0  0  0  0  0999 V2000
   -1.4296   -1.0979    2.4038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600   -0.7962    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6460   -0.4283    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.5683   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.3079   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3062    0.0136    0.3351 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716    1.1350    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850    1.1962   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1956   -0.0596    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -0.0912    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919   -1.1326    2.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6769    0.9450    2.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.0290   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0072   -0.7645   -1.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2794   -0.6681   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1541    0.2445   -1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7407    1.0459   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4387    0.9373    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871   -1.1962   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -1.2278    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7612   -1.3475   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5784   -2.6523    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5828   -3.5818    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7657   -3.2180   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9595   -1.9392   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539   -1.0232   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484    1.0081    0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119    1.5976    1.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640    2.9325    1.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618    3.6882    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003    3.1037   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3519    1.7897   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949   -0.4147   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686   -1.6300   -0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157    0.2922   -1.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    1.3847   -0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3976    1.1399    1.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    2.0530    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9709    2.1067   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    1.0227   -1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186    0.8430    3.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2810   -1.4738   -1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5800   -1.3271   -2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1749    0.3176   -1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4397    1.7612    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199    1.6164    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2771   -1.0578   -1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634   -2.1886   -0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4134   -1.9148   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9896   -1.7701    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6463   -2.9379    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492   -4.5912    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872   -3.9334   -0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8683   -1.5962   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822   -0.0274   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752    1.0153    2.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4953    3.3596    2.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358    4.7104    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    3.7286   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    1.3305   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  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 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9 19  1  0
 19 20  1  0
  3 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  3 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 20  6  1  0
 26 21  1  0
 32 27  1  0
 18 13  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 32 60  1  0
M  END

1501
  Mrv0541 02231215312D          

 32 35  0  0  0  0            999 V2000
    3.6020    2.8717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704    3.6842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    0.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -1.5553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396    2.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716    2.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3283    3.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469    2.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -2.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9603    4.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8788    2.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7356    3.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8396   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -4.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 13  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 21  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  5 13  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 14  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 21  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 23  2  0  0  0  0
 17 25  1  0  0  0  0
 18 24  2  0  0  0  0
 18 26  1  0  0  0  0
 19 22  2  0  0  0  0
 20 22  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 25 29  2  0  0  0  0
 26 30  2  0  0  0  0
 27 31  2  0  0  0  0
 28 32  2  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251256

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H28N2O2/c29-22-28(24-12-6-2-7-13-24,25-14-8-3-9-15-25)18-21-30-19-16-27(17-20-30,26(31)32)23-10-4-1-5-11-23/h1-15H,16-21H2,(H,31,32)

> <INCHI_KEY>
UFIVBRCCIRTJTN-UHFFFAOYSA-N

> <FORMULA>
C28H28N2O2

> <MOLECULAR_WEIGHT>
424.5341

> <EXACT_MASS>
424.21507815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
47.561259541801356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
2.649648205037271

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3836011909163433

> <JCHEM_PKA_STRONGEST_BASIC>
9.406326236510976

> <JCHEM_POLAR_SURFACE_AREA>
64.33

> <JCHEM_REFRACTIVITY>
137.2442

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
difenoxin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251256
     RDKit          3D
Difenoxin
 60 63  0  0  0  0  0  0  0  0999 V2000
   -1.4296   -1.0979    2.4038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600   -0.7962    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6460   -0.4283    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.5683   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.3079   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3062    0.0136    0.3351 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716    1.1350    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850    1.1962   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1956   -0.0596    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -0.0912    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919   -1.1326    2.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6769    0.9450    2.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.0290   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0072   -0.7645   -1.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2794   -0.6681   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1541    0.2445   -1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7407    1.0459   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4387    0.9373    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871   -1.1962   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -1.2278    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7612   -1.3475   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5784   -2.6523    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5828   -3.5818    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7657   -3.2180   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9595   -1.9392   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539   -1.0232   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484    1.0081    0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119    1.5976    1.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640    2.9325    1.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618    3.6882    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003    3.1037   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3519    1.7897   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949   -0.4147   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686   -1.6300   -0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157    0.2922   -1.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    1.3847   -0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3976    1.1399    1.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    2.0530    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9709    2.1067   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    1.0227   -1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186    0.8430    3.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2810   -1.4738   -1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5800   -1.3271   -2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1749    0.3176   -1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4397    1.7612    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199    1.6164    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2771   -1.0578   -1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634   -2.1886   -0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4134   -1.9148   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9896   -1.7701    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6463   -2.9379    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492   -4.5912    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872   -3.9334   -0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8683   -1.5962   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822   -0.0274   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752    1.0153    2.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4953    3.3596    2.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358    4.7104    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    3.7286   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    1.3305   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  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 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9 19  1  0
 19 20  1  0
  3 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  3 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 20  6  1  0
 26 21  1  0
 32 27  1  0
 18 13  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 32 60  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1501                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.724   5.361   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.531   6.877   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       9.034   0.947   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      10.780  -2.903   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.034   4.027   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.368   3.257   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.700   3.257   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.368   1.717   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.700   1.717   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034  -0.593   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.214   5.017   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.700  -1.363   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   5.361   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.700  -2.903   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.946   6.534   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.661   4.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.700  -4.443   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.160  -2.903   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.126   7.523   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.840   5.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.240  -2.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.573   6.997   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.034  -5.213   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.390  -4.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.366  -5.213   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.390  -1.570   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.034  -6.753   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.850  -4.237   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.366  -6.753   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.850  -1.570   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.700  -7.523   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.080  -2.903   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3    8    9   10                                                  
CONECT    4   21                                                            
CONECT    5    6    7   11   13                                             
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    3    6                                                       
CONECT    9    3    7                                                       
CONECT   10    3   12                                                       
CONECT   11    5   15   16                                                  
CONECT   12   10   14                                                       
CONECT   13    1    2    5                                                  
CONECT   14   12   17   18   21                                             
CONECT   15   11   19                                                       
CONECT   16   11   20                                                       
CONECT   17   14   23   25                                                  
CONECT   18   14   24   26                                                  
CONECT   19   15   22                                                       
CONECT   20   16   22                                                       
CONECT   21    4   14                                                       
CONECT   22   19   20                                                       
CONECT   23   17   27                                                       
CONECT   24   18   28                                                       
CONECT   25   17   29                                                       
CONECT   26   18   30                                                       
CONECT   27   23   31                                                       
CONECT   28   24   32                                                       
CONECT   29   25   31                                                       
CONECT   30   26   32                                                       
CONECT   31   27   29                                                       
CONECT   32   28   30                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0251256
HETATM    1  N1  UNL     1      -1.430  -1.098   2.404  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.960  -0.796   1.398  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.646  -0.428   0.164  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.662  -0.568  -0.984  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.475   0.308  -0.827  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.306   0.014   0.335  1.00  0.00           N  
HETATM    7  C5  UNL     1       1.172   1.135   0.630  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.385   1.196  -0.236  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.196  -0.060   0.183  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.252  -0.091   1.652  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.892  -1.133   2.268  1.00  0.00           O  
HETATM   12  O2  UNL     1       3.677   0.945   2.465  1.00  0.00           O  
HETATM   13  C9  UNL     1       4.566   0.029  -0.372  1.00  0.00           C  
HETATM   14  C10 UNL     1       5.007  -0.765  -1.411  1.00  0.00           C  
HETATM   15  C11 UNL     1       6.279  -0.668  -1.918  1.00  0.00           C  
HETATM   16  C12 UNL     1       7.154   0.245  -1.380  1.00  0.00           C  
HETATM   17  C13 UNL     1       6.741   1.046  -0.346  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.439   0.937   0.161  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.387  -1.196  -0.341  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.029  -1.228   0.244  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.761  -1.348  -0.041  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.578  -2.652   0.433  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.583  -3.582   0.272  1.00  0.00           C  
HETATM   24  C20 UNL     1      -5.766  -3.218  -0.358  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.959  -1.939  -0.828  1.00  0.00           C  
HETATM   26  C22 UNL     1      -4.954  -1.023  -0.662  1.00  0.00           C  
HETATM   27  C23 UNL     1      -3.048   1.008   0.320  1.00  0.00           C  
HETATM   28  C24 UNL     1      -3.112   1.598   1.561  1.00  0.00           C  
HETATM   29  C25 UNL     1      -3.464   2.933   1.768  1.00  0.00           C  
HETATM   30  C26 UNL     1      -3.762   3.688   0.660  1.00  0.00           C  
HETATM   31  C27 UNL     1      -3.700   3.104  -0.586  1.00  0.00           C  
HETATM   32  C28 UNL     1      -3.352   1.790  -0.771  1.00  0.00           C  
HETATM   33  H1  UNL     1      -2.195  -0.415  -1.952  1.00  0.00           H  
HETATM   34  H2  UNL     1      -1.369  -1.630  -0.989  1.00  0.00           H  
HETATM   35  H3  UNL     1       0.116   0.292  -1.766  1.00  0.00           H  
HETATM   36  H4  UNL     1      -0.820   1.385  -0.723  1.00  0.00           H  
HETATM   37  H5  UNL     1       1.398   1.140   1.712  1.00  0.00           H  
HETATM   38  H6  UNL     1       0.561   2.053   0.415  1.00  0.00           H  
HETATM   39  H7  UNL     1       2.971   2.107  -0.058  1.00  0.00           H  
HETATM   40  H8  UNL     1       2.097   1.023  -1.287  1.00  0.00           H  
HETATM   41  H9  UNL     1       4.019   0.843   3.385  1.00  0.00           H  
HETATM   42  H10 UNL     1       4.281  -1.474  -1.812  1.00  0.00           H  
HETATM   43  H11 UNL     1       6.580  -1.327  -2.753  1.00  0.00           H  
HETATM   44  H12 UNL     1       8.175   0.318  -1.788  1.00  0.00           H  
HETATM   45  H13 UNL     1       7.440   1.761   0.073  1.00  0.00           H  
HETATM   46  H14 UNL     1       5.220   1.616   0.966  1.00  0.00           H  
HETATM   47  H15 UNL     1       2.277  -1.058  -1.439  1.00  0.00           H  
HETATM   48  H16 UNL     1       2.863  -2.189  -0.190  1.00  0.00           H  
HETATM   49  H17 UNL     1       0.413  -1.915  -0.420  1.00  0.00           H  
HETATM   50  H18 UNL     1       0.990  -1.770   1.234  1.00  0.00           H  
HETATM   51  H19 UNL     1      -2.646  -2.938   0.936  1.00  0.00           H  
HETATM   52  H20 UNL     1      -4.449  -4.591   0.636  1.00  0.00           H  
HETATM   53  H21 UNL     1      -6.587  -3.933  -0.507  1.00  0.00           H  
HETATM   54  H22 UNL     1      -6.868  -1.596  -1.331  1.00  0.00           H  
HETATM   55  H23 UNL     1      -5.082  -0.027  -1.013  1.00  0.00           H  
HETATM   56  H24 UNL     1      -2.875   1.015   2.461  1.00  0.00           H  
HETATM   57  H25 UNL     1      -3.495   3.360   2.785  1.00  0.00           H  
HETATM   58  H26 UNL     1      -4.036   4.710   0.764  1.00  0.00           H  
HETATM   59  H27 UNL     1      -3.946   3.729  -1.462  1.00  0.00           H  
HETATM   60  H28 UNL     1      -3.299   1.330  -1.752  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   21   27
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7   20
CONECT    7    8   37   38
CONECT    8    9   39   40
CONECT    9   10   13   19
CONECT   10   11   11   12
CONECT   12   41
CONECT   13   14   14   18
CONECT   14   15   42
CONECT   15   16   16   43
CONECT   16   17   44
CONECT   17   18   18   45
CONECT   18   46
CONECT   19   20   47   48
CONECT   20   49   50
CONECT   21   22   22   26
CONECT   22   23   51
CONECT   23   24   24   52
CONECT   24   25   53
CONECT   25   26   26   54
CONECT   26   55
CONECT   27   28   28   32
CONECT   28   29   56
CONECT   29   30   30   57
CONECT   30   31   58
CONECT   31   32   32   59
CONECT   32   60
END

HMDB0251256
     RDKit          3D
Difenoxin
 60 63  0  0  0  0  0  0  0  0999 V2000
   -1.4296   -1.0979    2.4038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600   -0.7962    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6460   -0.4283    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.5683   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.3079   -0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3062    0.0136    0.3351 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716    1.1350    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850    1.1962   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1956   -0.0596    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -0.0912    1.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919   -1.1326    2.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6769    0.9450    2.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.0290   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0072   -0.7645   -1.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2794   -0.6681   -1.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1541    0.2445   -1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7407    1.0459   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4387    0.9373    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871   -1.1962   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -1.2278    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7612   -1.3475   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5784   -2.6523    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5828   -3.5818    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7657   -3.2180   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9595   -1.9392   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539   -1.0232   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484    1.0081    0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119    1.5976    1.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640    2.9325    1.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7618    3.6882    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003    3.1037   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3519    1.7897   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949   -0.4147   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3686   -1.6300   -0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157    0.2922   -1.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    1.3847   -0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3976    1.1399    1.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    2.0530    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9709    2.1067   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    1.0227   -1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186    0.8430    3.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2810   -1.4738   -1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5800   -1.3271   -2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1749    0.3176   -1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4397    1.7612    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2199    1.6164    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2771   -1.0578   -1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8634   -2.1886   -0.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4134   -1.9148   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9896   -1.7701    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6463   -2.9379    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492   -4.5912    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872   -3.9334   -0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8683   -1.5962   -1.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822   -0.0274   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752    1.0153    2.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4953    3.3596    2.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358    4.7104    0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    3.7286   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2987    1.3305   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  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 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9 19  1  0
 19 20  1  0
  3 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
  3 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 20  6  1  0
 26 21  1  0
 32 27  1  0
 18 13  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  0
 28 56  1  0
 29 57  1  0
 30 58  1  0
 31 59  1  0
 32 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(3-Cyano-3,3-diphenylpropyl)-4-phenylisonipecotic acid	ChEBI
Difenoxina	ChEBI
Difenoxinum	ChEBI
Diphenoxilic acid	ChEBI
Diphenoxylic acid	ChEBI
1-(3-Cyano-3,3-diphenylpropyl)-4-phenylisonipecotate	Generator
Diphenoxilate	Generator
Diphenoxylate	Generator
Difenoxin hydrochloride, 14C-labeled	MeSH
Difenoxin hydrochloride	MeSH

Chemical Formula

C₂₈H₂₈N₂O₂

Average Molecular Weight

424.5341

Monoisotopic Molecular Weight

424.21507815

IUPAC Name

1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid

Traditional Name

difenoxin

CAS Registry Number

Not Available

SMILES

OC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C28H28N2O2/c29-22-28(24-12-6-2-7-13-24,25-14-8-3-9-15-25)18-21-30-19-16-27(17-20-30,26(31)32)23-10-4-1-5-11-23/h1-15H,16-21H2,(H,31,32)

InChI Key

UFIVBRCCIRTJTN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylacetonitriles. These are cyclic aromatic compounds containing a diphenylacetonitrile moiety, which consists of a diphenylmethane linked to and acetonitrile to form 2,2-diphenylacetonitrile.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylacetonitriles

Direct Parent

Diphenylacetonitriles

Alternative Parents

Substituents

Diphenylacetonitrile
Diphenylmethane
Phenylpiperidine
Piperidinecarboxylic acid
Aralkylamine
Piperidine
Amino acid or derivatives
Amino acid
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonitrile
Nitrile
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amine (CHEBI:4534 )
piperidinemonocarboxylic acid (CHEBI:4534 )
nitrile (CHEBI:4534 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0251256)

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	4.39	ALOGPS
logP	2.65	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.33 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.24 m³·mol⁻¹	ChemAxon
Polarizability	47.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	201.899	30932474
DeepCCS	[M-H]-	199.541	30932474
DeepCCS	[M-2H]-	232.833	30932474
DeepCCS	[M+Na]+	208.061	30932474
AllCCS	[M+H]+	205.4	32859911
AllCCS	[M+H-H2O]+	203.1	32859911
AllCCS	[M+NH4]+	207.5	32859911
AllCCS	[M+Na]+	208.2	32859911
AllCCS	[M-H]-	204.0	32859911
AllCCS	[M+Na-2H]-	203.9	32859911
AllCCS	[M+HCOO]-	203.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.6236 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2208.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	253.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	223.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	573.0 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	499.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	233.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1185.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	553.3 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	1460.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	329.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	242.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	220.1 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Difenoxin	OC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1	3872.1	Standard polar	33892256
Difenoxin	OC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1	3197.2	Standard non polar	33892256
Difenoxin	OC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)C1=CC=CC=C1	3325.9	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 - Difenoxin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00vi-4594000000-592428f9d29c6f985192	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Difenoxin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Difenoxin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Difenoxin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Difenoxin 10V, Positive-QTOF	splash10-056r-0013900000-6d0509703a1aeec27ae9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 20V, Positive-QTOF	splash10-0c2c-0339300000-d349b4585ed57b3e9a0a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 40V, Positive-QTOF	splash10-00di-0963000000-a9637f11bc12d510f9c7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 10V, Negative-QTOF	splash10-00di-0003900000-8b709fa8ebb5bb2baa07	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 20V, Negative-QTOF	splash10-00b9-1549500000-ffaf76069ceaf59f5fc4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 40V, Negative-QTOF	splash10-06vl-4920000000-60617e604e89a34bbb59	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 10V, Positive-QTOF	splash10-004i-0002900000-e1c2bfc5313761b048d0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 20V, Positive-QTOF	splash10-004i-0119200000-59d346f8462209b6d01d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 40V, Positive-QTOF	splash10-014l-0912200000-8accad1ed1e964ebcd7a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 10V, Negative-QTOF	splash10-00di-0000900000-ca723da07ef4bcdae414	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 20V, Negative-QTOF	splash10-00dl-0007900000-db96e710b14faa0dc476	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Difenoxin 40V, Negative-QTOF	splash10-00di-4758900000-42912b18f7a0e713fb55	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

DB01501

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31620

KEGG Compound ID

C07871

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Difenoxin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

4534

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 Difenoxin (HMDB0251256)

MOL for HMDB0251256 (Difenoxin)

3D MOL for HMDB0251256 (Difenoxin)

3D SDF for HMDB0251256 (Difenoxin)

3D-SDF for HMDB0251256 (Difenoxin)

PDB for HMDB0251256 (Difenoxin)

3D PDB for HMDB0251256 (Difenoxin)

SMILES for HMDB0251256 (Difenoxin)

INCHI for HMDB0251256 (Difenoxin)

Structure for HMDB0251256 (Difenoxin)

3D Structure for HMDB0251256 (Difenoxin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra