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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:43:41 UTC

Update Date

2021-09-26 22:54:16 UTC

HMDB ID

HMDB0245672

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Drometrizole

Description

2-(2H-1,2,3-benzotriazol-2-yl)-4-methylphenol belongs to the class of organic compounds known as phenyl-1,2,3-triazoles. These are organic compounds containing a 1,2,3-triazole substituted by a phenyl group. Based on a literature review very few articles have been published on 2-(2H-1,2,3-benzotriazol-2-yl)-4-methylphenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Drometrizole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Drometrizole 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

  Mrv1572004191603102D          

 17 19  0  0  0  0            999 V2000
   -1.8212    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
  9  1  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245672

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(N2N=C3C=CC=CC3=N2)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H11N3O/c1-9-6-7-13(17)12(8-9)16-14-10-4-2-3-5-11(10)15-16/h2-8,17H,1H3

> <INCHI_KEY>
MCPKSFINULVDNX-UHFFFAOYSA-N

> <FORMULA>
C13H11N3O

> <MOLECULAR_WEIGHT>
225.251

> <EXACT_MASS>
225.090211986

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
24.18236567220858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,2,3-benzotriazol-2-yl)-4-methylphenol

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.1861999999999995

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.665730051769446

> <JCHEM_PKA_STRONGEST_BASIC>
-0.38314418261557803

> <JCHEM_POLAR_SURFACE_AREA>
50.94

> <JCHEM_REFRACTIVITY>
76.39590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
drometrizole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      -3.400   5.510   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       1.220   2.843   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -0.320   0.175   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    7    9                                                       
CONECT    7    6   13                                                       
CONECT    8    9   12                                                       
CONECT    9    1    6    8                                                  
CONECT   10    4   11   14                                                  
CONECT   11    5   10   15                                                  
CONECT   12    8   13   16                                                  
CONECT   13    7   12   17                                                  
CONECT   14   10   16                                                       
CONECT   15   11   16                                                       
CONECT   16   12   14   15                                                  
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0245672
HETATM    1  C1  UNL     1      -3.959   2.072   0.613  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.198   0.853   0.215  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.888  -0.255  -0.243  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.196  -1.387  -0.613  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.800  -1.406  -0.522  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.145  -2.557  -0.902  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.091  -0.315  -0.069  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.333  -0.313   0.031  1.00  0.00           N  
HETATM    9  N2  UNL     1       1.084   0.642  -0.484  1.00  0.00           N  
HETATM   10  C7  UNL     1       2.367   0.381  -0.237  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.515   1.077  -0.571  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.724   0.588  -0.193  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.817  -0.589   0.516  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.649  -1.273   0.841  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.410  -0.800   0.470  1.00  0.00           C  
HETATM   16  N3  UNL     1       1.135  -1.189   0.611  1.00  0.00           N  
HETATM   17  C13 UNL     1      -1.820   0.799   0.292  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.138   2.715  -0.272  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.319   2.662   1.299  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.926   1.832   1.091  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.979  -0.257  -0.320  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.698  -2.273  -0.976  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.139  -2.580  -0.841  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.463   1.997  -1.123  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.660   1.109  -0.437  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.761  -1.015   0.837  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.686  -2.200   1.396  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.306   1.683   0.655  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6    7
CONECT    6   23
CONECT    7    8   17   17
CONECT    8    9   16
CONECT    9   10   10
CONECT   10   11   15
CONECT   11   12   12   24
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15   27
CONECT   15   16   16
CONECT   17   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benazol II	MeSH
Benazol P	MeSH
2-(2'-Hydroxy-5'-methylphenyl)benzotriazole	MeSH
Tinuvin II	MeSH
2-(2'-Hydroxy-5-methylphenyl)benzotriazole	MeSH
Tinuvin P	MeSH

Chemical Formula

C₁₃H₁₁N₃O

Average Molecular Weight

225.251

Monoisotopic Molecular Weight

225.090211986

IUPAC Name

2-(2H-1,2,3-benzotriazol-2-yl)-4-methylphenol

Traditional Name

drometrizole

CAS Registry Number

Not Available

SMILES

CC1=CC(N2N=C3C=CC=CC3=N2)=C(O)C=C1

InChI Identifier

InChI=1S/C13H11N3O/c1-9-6-7-13(17)12(8-9)16-14-10-4-2-3-5-11(10)15-16/h2-8,17H,1H3

InChI Key

MCPKSFINULVDNX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenyl-1,2,3-triazoles. These are organic compounds containing a 1,2,3-triazole substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Triazoles

Direct Parent

Phenyl-1,2,3-triazoles

Alternative Parents

Substituents

Phenyl-1,2,3-triazole
Benzotriazole
P-cresol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.64	ALOGPS
logP	3.19	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-0.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.94 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.4 m³·mol⁻¹	ChemAxon
Polarizability	24.18 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]+	157.252	30932474
DeepCCS	[M-H]-	154.856	30932474
DeepCCS	[M-2H]-	187.822	30932474
DeepCCS	[M+Na]+	163.297	30932474
AllCCS	[M+H]+	149.8	32859911
AllCCS	[M+H-H2O]+	145.7	32859911
AllCCS	[M+NH4]+	153.6	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	152.7	32859911
AllCCS	[M+Na-2H]-	152.0	32859911
AllCCS	[M+HCOO]-	151.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Drometrizole	CC1=CC(N2N=C3C=CC=CC3=N2)=C(O)C=C1	2896.0	Standard polar	33892256
Drometrizole	CC1=CC(N2N=C3C=CC=CC3=N2)=C(O)C=C1	2043.3	Standard non polar	33892256
Drometrizole	CC1=CC(N2N=C3C=CC=CC3=N2)=C(O)C=C1	2076.7	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 - Drometrizole GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-2970000000-287e90851ed6ea6bad58	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Drometrizole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Drometrizole GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Drometrizole 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 - Drometrizole 10V, Positive-QTOF	splash10-004i-0090000000-ea9c1f034b3c17b33ecd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 20V, Positive-QTOF	splash10-004i-2490000000-fd0e18d49aa52fffc397	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 40V, Positive-QTOF	splash10-0006-9400000000-048d50480b8fc8894dec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 10V, Negative-QTOF	splash10-00di-0090000000-8479687603f666680e66	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 20V, Negative-QTOF	splash10-00di-0490000000-3f813bb8dd36ce1c9590	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 40V, Negative-QTOF	splash10-014i-1900000000-eb91ccde455a0abb6c3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 10V, Positive-QTOF	splash10-004i-0290000000-30a70b201dd6726bc648	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 20V, Positive-QTOF	splash10-05fr-2900000000-c3bc7879770445a52de8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 40V, Positive-QTOF	splash10-05i4-3910000000-dfc47510b0ccf5a81487	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 10V, Negative-QTOF	splash10-00xr-0890000000-ea41c68ca58a55ef68a0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 20V, Negative-QTOF	splash10-00xr-0490000000-b2f1c96426576ecca8d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drometrizole 40V, Negative-QTOF	splash10-00kf-0910000000-a06aa5dc40f57d748b80	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

16197

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1300601

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 Drometrizole (HMDB0245672)

MOL for HMDB0245672 (Drometrizole)

3D MOL for HMDB0245672 (Drometrizole)

3D SDF for HMDB0245672 (Drometrizole)

3D-SDF for HMDB0245672 (Drometrizole)

PDB for HMDB0245672 (Drometrizole)

3D PDB for HMDB0245672 (Drometrizole)

SMILES for HMDB0245672 (Drometrizole)

INCHI for HMDB0245672 (Drometrizole)

Structure for HMDB0245672 (Drometrizole)

3D Structure for HMDB0245672 (Drometrizole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra