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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:35:57 UTC

Update Date

2021-09-26 23:06:22 UTC

HMDB ID

HMDB0253255

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hydroxyaniline mustard

Description

Hydroxyaniline 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  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

$$$$

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

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-N,N-Bis(2-chloroethyl)aminophenol	HMDB
Hydroxyaniline mustard hydrobromide	HMDB
Hydroxyaniline mustard hydrochloride	HMDB
p-(Di-2-chloroethyl)aminophenol	HMDB
Phenol mustard drug	HMDB

Chemical Formula

C₁₀H₁₃Cl₂NO

Average Molecular Weight

234.12

Monoisotopic Molecular Weight

233.0374194

IUPAC Name

4-[bis(2-chloroethyl)amino]phenol

Traditional Name

hydroxyaniline mustard

CAS Registry Number

Not 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 Key

WRVLEDLJKOSANT-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.79	ALOGPS
logP	3.11	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.3	ChemAxon
pKa (Strongest Basic)	2.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.15 m³·mol⁻¹	ChemAxon
Polarizability	23.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	148.21	30932474
DeepCCS	[M-H]-	145.619	30932474
DeepCCS	[M-2H]-	181.248	30932474
DeepCCS	[M+Na]+	155.848	30932474
AllCCS	[M+H]+	146.5	32859911
AllCCS	[M+H-H2O]+	142.8	32859911
AllCCS	[M+NH4]+	149.9	32859911
AllCCS	[M+Na]+	150.9	32859911
AllCCS	[M-H]-	146.1	32859911
AllCCS	[M+Na-2H]-	146.8	32859911
AllCCS	[M+HCOO]-	147.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyaniline mustard	OC1=CC=C(C=C1)N(CCCl)CCCl	2909.8	Standard polar	33892256
Hydroxyaniline mustard	OC1=CC=C(C=C1)N(CCCl)CCCl	2102.3	Standard non polar	33892256
Hydroxyaniline mustard	OC1=CC=C(C=C1)N(CCCl)CCCl	1951.3	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 - Hydroxyaniline mustard GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1900000000-18c811bc1712e2f3103c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyaniline mustard GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyaniline mustard GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyaniline mustard GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Hydroxyaniline mustard 10V, Positive-QTOF	splash10-001i-0090000000-524f8b38cf6871dcc95f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyaniline mustard 20V, Positive-QTOF	splash10-001i-0690000000-9b171dd6dade25a9f70d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyaniline mustard 40V, Positive-QTOF	splash10-01q0-3900000000-40d1b49b5ae0ba941f89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyaniline mustard 10V, Negative-QTOF	splash10-01q9-7900000000-6d4dc08f2bd671453626	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyaniline mustard 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyaniline mustard 40V, Negative-QTOF	splash10-001i-9000000000-0477745f5eb6c39cf478	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

64161

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71000

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 Hydroxyaniline mustard (HMDB0253255)

MOL for HMDB0253255 (Hydroxyaniline mustard)

3D MOL for HMDB0253255 (Hydroxyaniline mustard)

3D SDF for HMDB0253255 (Hydroxyaniline mustard)

3D-SDF for HMDB0253255 (Hydroxyaniline mustard)

PDB for HMDB0253255 (Hydroxyaniline mustard)

3D PDB for HMDB0253255 (Hydroxyaniline mustard)

SMILES for HMDB0253255 (Hydroxyaniline mustard)

INCHI for HMDB0253255 (Hydroxyaniline mustard)

Structure for HMDB0253255 (Hydroxyaniline mustard)

3D Structure for HMDB0253255 (Hydroxyaniline mustard)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra