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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2023-02-21 17:18:16 UTC

HMDB ID

HMDB0014738

Secondary Accession Numbers

HMDB14738

Metabolite Identification

Common Name

Monobenzone

Description

Monobenzone is the monobenzyl ether of hydroquinone used medically for depigmentation. Monobenzone occurs as a white, almost tasteless crystalline powder, soluble in alcohol and practically insoluble in water. The topical application of monobenzone in animals increases the excretion of melanin from the melanocytes. The same action is thought to be responsible for the depigmenting effect of the drug in humans. Monobenzone may cause destruction of melanocytes and permanent depigmentation.

Structure

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

600
  Mrv0541 02231214482D          

 15 16  0  0  0  0            999 V2000
    2.3644    0.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    2.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    3.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014738

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(OCC2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2

> <INCHI_KEY>
VYQNWZOUAUKGHI-UHFFFAOYSA-N

> <FORMULA>
C13H12O2

> <MOLECULAR_WEIGHT>
200.2332

> <EXACT_MASS>
200.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.9104443930156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(benzyloxy)phenol

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
3.236482346

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.914679353242907

> <JCHEM_PKA_STRONGEST_BASIC>
-4.848361687075011

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
59.11470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
superlite

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 600                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.414   0.624   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414  -5.536   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.747   2.934   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.747   1.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -0.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   3.704   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   3.704   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -1.686   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -1.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   5.244   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   5.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747   6.014   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -3.226   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747  -3.226   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -3.996   0.000  0.00  0.00           C+0
CONECT    1    4    5                                                       
CONECT    2   15                                                            
CONECT    3    4    6    7                                                  
CONECT    4    1    3                                                       
CONECT    5    1    8    9                                                  
CONECT    6    3   10                                                       
CONECT    7    3   11                                                       
CONECT    8    5   13                                                       
CONECT    9    5   14                                                       
CONECT   10    6   12                                                       
CONECT   11    7   12                                                       
CONECT   12   10   11                                                       
CONECT   13    8   15                                                       
CONECT   14    9   15                                                       
CONECT   15    2   13   14                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0014738
HETATM    1  O1  UNL     1       5.736  -0.345   0.006  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.359  -0.225   0.148  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.812   0.235   1.328  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.447   0.352   1.466  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.565   0.022   0.449  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.183   0.152   0.619  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.649  -0.206  -0.469  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.071  -0.011  -0.128  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.807  -1.033   0.445  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.132  -0.887   0.775  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.787   0.307   0.542  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.070   1.326  -0.025  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.732   1.187  -0.361  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.114  -0.437  -0.729  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.480  -0.555  -0.867  1.00  0.00           C  
HETATM   16  H1  UNL     1       6.222   0.470  -0.354  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.450   0.511   2.164  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.002   0.716   2.397  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.478  -1.294  -0.712  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.356   0.332  -1.412  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.313  -1.973   0.634  1.00  0.00           H  
HETATM   22  H7  UNL     1      -4.662  -1.722   1.222  1.00  0.00           H  
HETATM   23  H8  UNL     1      -5.835   0.423   0.802  1.00  0.00           H  
HETATM   24  H9  UNL     1      -4.613   2.266  -0.201  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.190   2.001  -0.805  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.426  -0.694  -1.520  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.897  -0.916  -1.795  1.00  0.00           H  
CONECT    1    2   16
CONECT    2    3    3   15
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   14
CONECT    6    7
CONECT    7    8   19   20
CONECT    8    9    9   13
CONECT    9   10   21
CONECT   10   11   11   22
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   25
CONECT   14   15   15   26
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(Benzyloxyl)phenol	ChEBI
4-(Phenylmethoxy)phenol	ChEBI
4-Benzyloxy-phenol	ChEBI
4-Benzyloxyphenol	ChEBI
Benzyl p-hydroxyphenyl ether	ChEBI
Hydroquinone benzyl ether	ChEBI
Hydroquinone monobenzyl ether	ChEBI
Monobenzona	ChEBI
Monobenzonum	ChEBI
MONOBENZYL ether OF hydroquinone	ChEBI
Monobenzyl hydroquinone	ChEBI
p-(Benzyloxy)phenol	ChEBI
p-Hydroxyphenyl benzyl ether	ChEBI
Benoquin	Kegg
Benzoquin	HMDB
Benzyl hydroquinone	HMDB
Monobenzyl ether hydroquinone	HMDB
Novo-depigman	HMDB
ICN brand OF monobenzone	HMDB
Agerite alba	HMDB

Chemical Formula

C₁₃H₁₂O₂

Average Molecular Weight

200.2332

Monoisotopic Molecular Weight

200.083729628

IUPAC Name

4-(benzyloxy)phenol

Traditional Name

superlite

CAS Registry Number

103-16-2

SMILES

OC1=CC=C(OCC2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2

InChI Key

VYQNWZOUAUKGHI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzyl ether (CHEBI:34380 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014738)
Membrane (HMDB: HMDB0014738)

Source

Exogenous

Exogenous (HMDB: HMDB0014738)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	110 - 118 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.039 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	3.08	ALOGPS
logP	3.24	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.11 m³·mol⁻¹	ChemAxon
Polarizability	21.91 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	145.481	31661259
DarkChem	[M-H]-	145.465	31661259
DeepCCS	[M+H]+	141.852	30932474
DeepCCS	[M-H]-	139.456	30932474
DeepCCS	[M-2H]-	174.815	30932474
DeepCCS	[M+Na]+	149.298	30932474
AllCCS	[M+H]+	144.6	32859911
AllCCS	[M+H-H2O]+	140.3	32859911
AllCCS	[M+NH4]+	148.6	32859911
AllCCS	[M+Na]+	149.7	32859911
AllCCS	[M-H]-	147.6	32859911
AllCCS	[M+Na-2H]-	147.5	32859911
AllCCS	[M+HCOO]-	147.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Monobenzone	OC1=CC=C(OCC2=CC=CC=C2)C=C1	3194.8	Standard polar	33892256
Monobenzone	OC1=CC=C(OCC2=CC=CC=C2)C=C1	1844.5	Standard non polar	33892256
Monobenzone	OC1=CC=C(OCC2=CC=CC=C2)C=C1	1847.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Monobenzone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(OCC2=CC=CC=C2)C=C1	1922.8	Semi standard non polar	33892256
Monobenzone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(OCC2=CC=CC=C2)C=C1	2212.1	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 - Monobenzone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9110000000-025722658da7cc1290d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monobenzone GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9330000000-3eaa17644c5b236db8da	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monobenzone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monobenzone 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 - Monobenzone 10V, Positive-QTOF	splash10-0udi-1190000000-3595b5030a4ebc2347c2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 20V, Positive-QTOF	splash10-0udl-9380000000-a97bc5e4be8acb8419d1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 40V, Positive-QTOF	splash10-0006-9000000000-5b165e47c98443994ad9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 10V, Negative-QTOF	splash10-0002-0900000000-e7b44cd98d5e6c8549d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 20V, Negative-QTOF	splash10-052b-0900000000-1bff4b9e2c443589d41d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 40V, Negative-QTOF	splash10-0a4i-8900000000-278866faee3a03db76a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 10V, Positive-QTOF	splash10-0006-9030000000-e38d4949da6c58c74761	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 20V, Positive-QTOF	splash10-0006-9020000000-20fb8a2262c9d69aa52d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 40V, Positive-QTOF	splash10-0006-9000000000-8acc13cd061317ce9128	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 10V, Negative-QTOF	splash10-0002-0900000000-4efe2cdd426a723e9362	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 20V, Negative-QTOF	splash10-0006-9000000000-ecda9a2576e7b8e3a651	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monobenzone 40V, Negative-QTOF	splash10-002f-9000000000-06b6cf392bec57e4cb4a	2021-10-11	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00600	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00600	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00600

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7356

KEGG Compound ID

C14244

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Monobenzone

METLIN ID

Not Available

PubChem Compound

7638

PDB ID

Not Available

ChEBI ID

34380

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

Not Available

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

References

Chen YR, Y-Y R, Lin TY, Huang CP, Tang WC, Chen ST, Lin SB: Identification of an Alkylhydroquinone from Rhus succedanea as an Inhibitor of Tyrosinase and Melanogenesis. J Agric Food Chem. 2009 Mar 25;57(6):2200-5. doi: 10.1021/jf802617a. [PubMed:19159217 ]

Showing metabocard for Monobenzone (HMDB0014738)

MOL for HMDB0014738 (Monobenzone)

3D MOL for HMDB0014738 (Monobenzone)

3D SDF for HMDB0014738 (Monobenzone)

3D-SDF for HMDB0014738 (Monobenzone)

PDB for HMDB0014738 (Monobenzone)

3D PDB for HMDB0014738 (Monobenzone)

SMILES for HMDB0014738 (Monobenzone)

INCHI for HMDB0014738 (Monobenzone)

Structure for HMDB0014738 (Monobenzone)

3D Structure for HMDB0014738 (Monobenzone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References