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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:13:45 UTC

Update Date

2021-09-26 22:55:05 UTC

HMDB ID

HMDB0246194

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate

Description

2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate, also known as naphthol as-D chloroacetate, belongs to the class of organic compounds known as naphthalene-2-carboxanilides. These are naphthalene-2-carboxamides, where the carboxamide group is substituted with an aniline. Based on a literature review very few articles have been published on 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-(o-tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate 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


  Mrv1652309112101142D          

 25 27  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   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
    2.1434    2.0625    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.1434   -1.2375    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

HMDB0246194
     RDKit          3D
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.9769    2.3480   -0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607    1.1828   -0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215    1.2168   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7116    0.1676    0.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0462   -0.9614    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494   -0.9927    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426    0.0486    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5384    0.0634   -0.1099 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -0.9604    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180   -2.0272    0.6814 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -0.9061   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316   -2.0826    0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827   -2.1930    0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5787   -3.3535    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -3.4381    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6437   -2.3652   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9850   -1.2131   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5998   -1.1263   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099    0.0116   -0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.1556   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    1.3869   -0.8261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1181    2.4365    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7293    2.1474    1.1667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    3.8081   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    3.9708   -1.7727 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4092    2.9512   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3275    2.0217   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478    3.0219   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5635    2.1074   -0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7848    0.1826    0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5318   -1.8189    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1516   -1.8962    0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522    0.9345   -0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9884   -2.9285    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828   -4.1887    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4355   -4.3829    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -2.4305   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4778   -0.3200   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    0.8714   -1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494    4.5831    0.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2040    3.9675    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
  7  2  1  0
 20 11  1  0
 18 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  8 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 24 40  1  0
 24 41  1  0
M  END


  Mrv1652309112101142D          

 25 27  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   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
    2.1434    2.0625    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.1434   -1.2375    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246194

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C20H16ClNO3/c1-13-6-2-5-9-17(13)22-20(24)16-10-14-7-3-4-8-15(14)11-18(16)25-19(23)12-21/h2-11H,12H2,1H3,(H,22,24)

> <INCHI_KEY>
FMVKYSCWHDVMGO-UHFFFAOYSA-N

> <FORMULA>
C20H16ClNO3

> <MOLECULAR_WEIGHT>
353.8

> <EXACT_MASS>
353.0818711

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
35.55611319043091

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2-methylphenyl)carbamoyl]naphthalen-2-yl 2-chloroacetate

> <ALOGPS_LOGP>
4.24

> <JCHEM_LOGP>
4.712633552000001

> <ALOGPS_LOGS>
-6.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.83807786372791

> <JCHEM_PKA_STRONGEST_BASIC>
-4.038131277441282

> <JCHEM_POLAR_SURFACE_AREA>
55.4

> <JCHEM_REFRACTIVITY>
98.96849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2-methylphenyl)carbamoyl]naphthalen-2-yl chloroacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246194
     RDKit          3D
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.9769    2.3480   -0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607    1.1828   -0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215    1.2168   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7116    0.1676    0.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0462   -0.9614    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494   -0.9927    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426    0.0486    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5384    0.0634   -0.1099 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -0.9604    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180   -2.0272    0.6814 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -0.9061   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316   -2.0826    0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827   -2.1930    0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5787   -3.3535    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -3.4381    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6437   -2.3652   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9850   -1.2131   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5998   -1.1263   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099    0.0116   -0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.1556   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    1.3869   -0.8261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1181    2.4365    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7293    2.1474    1.1667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    3.8081   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    3.9708   -1.7727 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4092    2.9512   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3275    2.0217   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478    3.0219   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5635    2.1074   -0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7848    0.1826    0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5318   -1.8189    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1516   -1.8962    0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522    0.9345   -0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9884   -2.9285    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828   -4.1887    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4355   -4.3829    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -2.4305   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4778   -0.3200   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    0.8714   -1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494    4.5831    0.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2040    3.9675    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
  7  2  1  0
 20 11  1  0
 18 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  8 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 24 40  1  0
 24 41  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   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
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0       1.334  -6.930   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0246194
HETATM    1  C1  UNL     1      -2.977   2.348  -0.938  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.661   1.183  -0.323  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.022   1.217  -0.152  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.712   0.168   0.409  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.046  -0.961   0.819  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.649  -0.993   0.642  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.943   0.049   0.082  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.538   0.063  -0.110  1.00  0.00           N  
HETATM    9  C8  UNL     1      -0.630  -0.960   0.190  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.118  -2.027   0.681  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.810  -0.906  -0.009  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.532  -2.083   0.286  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.883  -2.193   0.110  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.579  -3.354   0.402  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.943  -3.438   0.212  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.644  -2.365  -0.273  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.985  -1.213  -0.568  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.600  -1.126  -0.376  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.910   0.012  -0.662  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.521   0.156  -0.490  1.00  0.00           C  
HETATM   21  O2  UNL     1       0.964   1.387  -0.826  1.00  0.00           O  
HETATM   22  C19 UNL     1       1.118   2.436   0.108  1.00  0.00           C  
HETATM   23  O3  UNL     1       1.729   2.147   1.167  1.00  0.00           O  
HETATM   24  C20 UNL     1       0.588   3.808  -0.148  1.00  0.00           C  
HETATM   25 CL1  UNL     1      -0.054   3.971  -1.773  1.00  0.00          CL  
HETATM   26  H1  UNL     1      -2.409   2.951  -0.231  1.00  0.00           H  
HETATM   27  H2  UNL     1      -2.327   2.022  -1.777  1.00  0.00           H  
HETATM   28  H3  UNL     1      -3.748   3.022  -1.414  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.564   2.107  -0.473  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.785   0.183   0.549  1.00  0.00           H  
HETATM   31  H6  UNL     1      -5.532  -1.819   1.267  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.152  -1.896   0.978  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.152   0.935  -0.531  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.988  -2.928   0.667  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.983  -4.189   0.787  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.436  -4.383   0.462  1.00  0.00           H  
HETATM   37  H12 UNL     1       6.719  -2.430  -0.423  1.00  0.00           H  
HETATM   38  H13 UNL     1       5.478  -0.320  -0.957  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.464   0.871  -1.048  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.349   4.583   0.078  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.204   3.967   0.639  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3    7
CONECT    3    4   29
CONECT    4    5    5   30
CONECT    5    6   31
CONECT    6    7    7   32
CONECT    7    8
CONECT    8    9   33
CONECT    9   10   10   11
CONECT   11   12   12   20
CONECT   12   13   34
CONECT   13   14   14   18
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   19
CONECT   19   20   20   39
CONECT   20   21
CONECT   21   22
CONECT   22   23   23   24
CONECT   24   25   40   41
END

HMDB0246194
     RDKit          3D
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.9769    2.3480   -0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607    1.1828   -0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215    1.2168   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7116    0.1676    0.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0462   -0.9614    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494   -0.9927    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426    0.0486    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5384    0.0634   -0.1099 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -0.9604    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180   -2.0272    0.6814 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -0.9061   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316   -2.0826    0.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827   -2.1930    0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5787   -3.3535    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -3.4381    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6437   -2.3652   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9850   -1.2131   -0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5998   -1.1263   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099    0.0116   -0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.1556   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    1.3869   -0.8261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1181    2.4365    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7293    2.1474    1.1667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    3.8081   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    3.9708   -1.7727 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4092    2.9512   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3275    2.0217   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478    3.0219   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5635    2.1074   -0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7848    0.1826    0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5318   -1.8189    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1516   -1.8962    0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522    0.9345   -0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9884   -2.9285    0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828   -4.1887    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4355   -4.3829    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7194   -2.4305   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4778   -0.3200   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    0.8714   -1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494    4.5831    0.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2040    3.9675    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
  7  2  1  0
 20 11  1  0
 18 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  8 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 24 40  1  0
 24 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetic acid	Generator
Naphthol as-D chloroacetate	HMDB

Chemical Formula

C₂₀H₁₆ClNO₃

Average Molecular Weight

353.8

Monoisotopic Molecular Weight

353.0818711

IUPAC Name

3-[(2-methylphenyl)carbamoyl]naphthalen-2-yl 2-chloroacetate

Traditional Name

3-[(2-methylphenyl)carbamoyl]naphthalen-2-yl chloroacetate

CAS Registry Number

Not Available

SMILES

CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl

InChI Identifier

InChI=1S/C20H16ClNO3/c1-13-6-2-5-9-17(13)22-20(24)16-10-14-7-3-4-8-15(14)11-18(16)25-19(23)12-21/h2-11H,12H2,1H3,(H,22,24)

InChI Key

FMVKYSCWHDVMGO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalene-2-carboxanilides. These are naphthalene-2-carboxamides, where the carboxamide group is substituted with an aniline.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalenecarboxylic acids and derivatives

Direct Parent

Naphthalene-2-carboxanilides

Alternative Parents

Substituents

Naphthalene-2-carboxanilide
Aromatic anilide
Toluene
Monocyclic benzene moiety
Alpha-halocarboxylic acid or derivatives
Alpha-halocarboxylic acid derivative
Secondary carboxylic acid amide
Carboxylic acid ester
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	4.24	ALOGPS
logP	4.71	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	12.84	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.97 m³·mol⁻¹	ChemAxon
Polarizability	35.56 Å³	ChemAxon
Number of Rings	3	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]+	175.063	30932474
DeepCCS	[M-H]-	172.705	30932474
DeepCCS	[M-2H]-	206.554	30932474
DeepCCS	[M+Na]+	181.781	30932474
AllCCS	[M+H]+	180.7	32859911
AllCCS	[M+H-H2O]+	177.6	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.4	32859911
AllCCS	[M-H]-	178.8	32859911
AllCCS	[M+Na-2H]-	177.9	32859911
AllCCS	[M+HCOO]-	177.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate	CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl	4246.8	Standard polar	33892256
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate	CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl	2964.3	Standard non polar	33892256
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate	CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl	3236.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate,1TMS,isomer #1	CC1=CC=CC=C1N(C(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl)[Si](C)(C)C	2958.7	Semi standard non polar	33892256
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate,1TMS,isomer #1	CC1=CC=CC=C1N(C(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl)[Si](C)(C)C	2895.5	Standard non polar	33892256
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate,1TMS,isomer #1	CC1=CC=CC=C1N(C(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl)[Si](C)(C)C	3897.2	Standard polar	33892256
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate,1TBDMS,isomer #1	CC1=CC=CC=C1N(C(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl)[Si](C)(C)C(C)(C)C	3215.8	Semi standard non polar	33892256
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate,1TBDMS,isomer #1	CC1=CC=CC=C1N(C(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl)[Si](C)(C)C(C)(C)C	3094.1	Standard non polar	33892256
2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate,1TBDMS,isomer #1	CC1=CC=CC=C1N(C(=O)C1=CC2=CC=CC=C2C=C1OC(=O)CCl)[Si](C)(C)C(C)(C)C	3898.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-3891000000-7ae3fecb774189e8cc4c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate 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 - 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate 10V, Positive-QTOF	splash10-0udj-0059000000-56d059a822d73ad80dac	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate 20V, Positive-QTOF	splash10-006t-0890000000-acc304ac0bfb3a054f8e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate 40V, Positive-QTOF	splash10-05fu-3930000000-c72f960f85c552401fab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate 10V, Negative-QTOF	splash10-0fvi-0059000000-f1bdc95eb8213f3a91fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate 20V, Negative-QTOF	splash10-01dl-4596000000-a09ed9b9dfe9420c3075	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate 40V, Negative-QTOF	splash10-00kf-1900000000-4e8dcc90de4425883c16	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

140845

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160247

PDB ID

Not Available

ChEBI ID

Not Available

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 2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate (HMDB0246194)

MOL for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

3D MOL for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

3D SDF for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

3D-SDF for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

PDB for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

3D PDB for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

SMILES for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

INCHI for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

Structure for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

3D Structure for HMDB0246194 (2-(O-Tolylcarbamoyl)naphthalen-3-yl 2-chloroacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra