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Showing metabocard for Hydroxyaniline mustard (HMDB0253255)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 11:35:57 UTC
Update Date2021-09-26 23:06:22 UTC
HMDB IDHMDB0253255
Secondary Accession NumbersNone
Metabolite Identification
Common NameHydroxyaniline mustard
DescriptionHydroxyaniline mustard, also known as phenol mustard drug, belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom. Based on a literature review very few articles have been published on Hydroxyaniline mustard. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hydroxyaniline mustard is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hydroxyaniline mustard 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0253255 (Hydroxyaniline mustard)

  Mrv1652309112113362D          

 14 14  0  0  0  0            999 V2000
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 N   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
Download

3D MOL for HMDB0253255 (Hydroxyaniline mustard)

HMDB0253255
     RDKit          3D
Hydroxyaniline mustard
 27 27  0  0  0  0  0  0  0  0999 V2000
    4.6947    0.3140    0.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002    0.2314    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896   -0.4843   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940   -0.5487   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5578    0.0734   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739   -0.0585   -0.4943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    1.1585   -0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708    1.6748    0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491    0.7758    0.7237 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468   -1.3814   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156   -2.0103    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2522   -2.0465    2.0596 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0556    0.7850    0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447    0.8629    0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.8500    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4349   -0.9894   -1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440   -1.1237   -1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231    2.0309   -0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405    1.1398   -1.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8136    2.7183    0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    1.9285    1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4911   -2.1187   -0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -1.5211   -1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1573   -1.8247    0.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244   -3.1489    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149    1.2929    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640    1.4203    1.7673 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  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  2  0
 14  2  1  0
  1 15  1  0
  3 16  1  0
  4 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
M  END
Download

3D SDF for HMDB0253255 (Hydroxyaniline mustard)

  Mrv1652309112113362D          

 14 14  0  0  0  0            999 V2000
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 N   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253255

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)N(CCCl)CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C10H13Cl2NO/c11-5-7-13(8-6-12)9-1-3-10(14)4-2-9/h1-4,14H,5-8H2

> <INCHI_KEY>
WRVLEDLJKOSANT-UHFFFAOYSA-N

> <FORMULA>
C10H13Cl2NO

> <MOLECULAR_WEIGHT>
234.12

> <EXACT_MASS>
233.0374194

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.65710833343085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[bis(2-chloroethyl)amino]phenol

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.106704041

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.299058933285103

> <JCHEM_PKA_STRONGEST_BASIC>
2.794537801188919

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
61.15410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyaniline mustard

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0253255 (Hydroxyaniline mustard)

HMDB0253255
     RDKit          3D
Hydroxyaniline mustard
 27 27  0  0  0  0  0  0  0  0999 V2000
    4.6947    0.3140    0.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002    0.2314    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896   -0.4843   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940   -0.5487   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5578    0.0734   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8739   -0.0585   -0.4943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    1.1585   -0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4708    1.6748    0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491    0.7758    0.7237 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468   -1.3814   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156   -2.0103    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2522   -2.0465    2.0596 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0556    0.7850    0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447    0.8629    0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.8500    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4349   -0.9894   -1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440   -1.1237   -1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231    2.0309   -0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405    1.1398   -1.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8136    2.7183    0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    1.9285    1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4911   -2.1187   -0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -1.5211   -1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1573   -1.8247    0.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244   -3.1489    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149    1.2929    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640    1.4203    1.7673 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  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  2  0
 14  2  1  0
  1 15  1  0
  3 16  1  0
  4 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
M  END
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PDB for HMDB0253255 (Hydroxyaniline mustard)

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       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.002  -3.080   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       5.335   0.000   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      10.669   0.000   0.000  0.00  0.00          Cl+0
HETATM   14  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0253255 (Hydroxyaniline mustard)

COMPND    HMDB0253255
HETATM    1  O1  UNL     1       4.695   0.314   0.238  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.300   0.231   0.067  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.790  -0.484  -0.985  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.394  -0.549  -1.128  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.558   0.073  -0.260  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.874  -0.058  -0.494  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.550   1.159  -0.578  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.471   1.675   0.438  1.00  0.00           C  
HETATM    9 CL1  UNL     1      -3.949   0.776   0.724  1.00  0.00          CL  
HETATM   10  C7  UNL     1      -1.347  -1.381  -0.579  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.116  -2.010   0.500  1.00  0.00           C  
HETATM   12 CL2  UNL     1      -1.252  -2.047   2.060  1.00  0.00          CL  
HETATM   13  C9  UNL     1       1.056   0.785   0.786  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.445   0.863   0.948  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.034   0.850   1.026  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.435  -0.989  -1.690  1.00  0.00           H  
HETATM   17  H3  UNL     1       1.044  -1.124  -1.971  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.823   2.031  -0.837  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.141   1.140  -1.571  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.814   2.718   0.114  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.946   1.928   1.417  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.491  -2.119  -0.817  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.975  -1.521  -1.537  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.157  -1.825   0.642  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.124  -3.149   0.224  1.00  0.00           H  
HETATM   26  H12 UNL     1       0.415   1.293   1.497  1.00  0.00           H  
HETATM   27  H13 UNL     1       2.864   1.420   1.767  1.00  0.00           H  
CONECT    1    2   15
CONECT    2    3    3   14
CONECT    3    4   16
CONECT    4    5    5   17
CONECT    5    6   13
CONECT    6    7   10
CONECT    7    8   18   19
CONECT    8    9   20   21
CONECT   10   11   22   23
CONECT   11   12   24   25
CONECT   13   14   14   26
CONECT   14   27
END
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SMILES for HMDB0253255 (Hydroxyaniline mustard)

OC1=CC=C(C=C1)N(CCCl)CCCl
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INCHI for HMDB0253255 (Hydroxyaniline mustard)

InChI=1S/C10H13Cl2NO/c11-5-7-13(8-6-12)9-1-3-10(14)4-2-9/h1-4,14H,5-8H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-N,N-Bis(2-chloroethyl)aminophenolHMDB
Hydroxyaniline mustard hydrobromideHMDB
Hydroxyaniline mustard hydrochlorideHMDB
p-(Di-2-chloroethyl)aminophenolHMDB
Phenol mustard drugHMDB
Chemical FormulaC10H13Cl2NO
Average Molecular Weight234.12
Monoisotopic Molecular Weight233.0374194
IUPAC Name4-[bis(2-chloroethyl)amino]phenol
Traditional Namehydroxyaniline mustard
CAS Registry NumberNot Available
SMILES
OC1=CC=C(C=C1)N(CCCl)CCCl
InChI Identifier
InChI=1S/C10H13Cl2NO/c11-5-7-13(8-6-12)9-1-3-10(14)4-2-9/h1-4,14H,5-8H2
InChI KeyWRVLEDLJKOSANT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • P-aminophenol
  • Aminophenol
  • Nitrogen mustard
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Aniline or substituted anilines
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary amine
  • Organopnictogen compound
  • Alkyl halide
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Alkyl chloride
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID64161
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71000
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]