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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-03-07 21:31:29 UTC

Update Date

2023-02-21 17:29:27 UTC

HMDB ID

HMDB0059824

Secondary Accession Numbers

HMDB59824

Metabolite Identification

Common Name

4-Hydroxy-3-methylacetophenone

Description

4-Hydroxy-3-methylacetophenone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-Hydroxy-3-methylacetophenone is an extremely weak basic (essentially neutral) compound (based on its pKa). These are organic compounds containing the acetophenone structure.

Structure

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

70135
  Mrv0541 12191221362D          

 21 21  0  0  0  0            999 V2000
    3.0789   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.9841    0.0000 O   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
    3.0789    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4909    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
    3.0789    1.5716    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
    1.9215    0.5899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.5899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -0.7466    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3942   -0.4604    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -1.1591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -1.3463    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0492    1.5412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    2.2399    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5377    2.4271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -1.9841    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 21  1  0  0  0  0
  2 10  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  2  0  0  0  0
  3  9  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  4 10  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 15  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 18  1  0  0  0  0
 11 19  1  0  0  0  0
 11 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059824

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]OC1=C(C([H])=C(C([H])=C1[H])C(=O)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O2/c1-6-5-8(7(2)10)3-4-9(6)11/h3-5,11H,1-2H3

> <INCHI_KEY>
LXBHHIZIQVZGFN-UHFFFAOYSA-N

> <FORMULA>
C9H10O2

> <MOLECULAR_WEIGHT>
150.1745

> <EXACT_MASS>
150.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.0710087528464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-hydroxy-3-methylphenyl)ethan-1-one

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.7407494023333332

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.72573976673659

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.152676412808889

> <JCHEM_PKA_STRONGEST_BASIC>
-6.911846045163828

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
43.4829

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-hydroxy-3-methylphenyl)ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-DEC-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 70135                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-DEC-12         0                                  
HETATM    1  O   UNK     0       5.747  -3.226   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414   3.704   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.414  -0.916   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   0.624   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -1.686   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   0.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -1.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747   2.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   3.704   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       3.587   1.101   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       7.908   1.101   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       7.908  -1.394   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.603  -0.859   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.253  -2.164   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.557  -2.513   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       7.558   2.877   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       7.908   4.181   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       6.604   4.531   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       6.574  -3.704   0.000  0.00  0.00           H+0
CONECT    1    6   21                                                       
CONECT    2   10                                                            
CONECT    3    5    6    9                                                  
CONECT    4    5    7   10                                                  
CONECT    5    3    4   12                                                  
CONECT    6    1    3    8                                                  
CONECT    7    4    8   13                                                  
CONECT    8    6    7   14                                                  
CONECT    9    3   15   16   17                                             
CONECT   10    2    4   11                                                  
CONECT   11   10   18   19   20                                             
CONECT   12    5                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19   11                                                            
CONECT   20   11                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-3-methylacetophenone	MeSH

Chemical Formula

C₉H₁₀O₂

Average Molecular Weight

150.1745

Monoisotopic Molecular Weight

150.068079564

IUPAC Name

1-(4-hydroxy-3-methylphenyl)ethan-1-one

Traditional Name

1-(4-hydroxy-3-methylphenyl)ethanone

CAS Registry Number

Not Available

SMILES

[H]OC1=C(C([H])=C(C([H])=C1[H])C(=O)C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C9H10O2/c1-6-5-8(7(2)10)3-4-9(6)11/h3-5,11H,1-2H3

InChI Key

LXBHHIZIQVZGFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acetophenone
Aryl alkyl ketone
O-cresol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0059824)

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
Water Solubility	2.79 g/L	ALOGPS
logP	1.85	ALOGPS
logP	1.74	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	8.15	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	43.48 m³·mol⁻¹	ChemAxon
Polarizability	16.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	134.79	31661259
DarkChem	[M-H]-	130.51	31661259
DeepCCS	[M+H]+	147.296	30932474
DeepCCS	[M-H]-	144.817	30932474
DeepCCS	[M-2H]-	178.986	30932474
DeepCCS	[M+Na]+	154.613	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	126.9	32859911
AllCCS	[M+NH4]+	135.3	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M-H]-	130.1	32859911
AllCCS	[M+Na-2H]-	131.5	32859911
AllCCS	[M+HCOO]-	133.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methylacetophenone	[H]OC1=C(C([H])=C(C([H])=C1[H])C(=O)C([H])([H])[H])C([H])([H])[H]	1813.2	Standard polar	33892256
4-Hydroxy-3-methylacetophenone	[H]OC1=C(C([H])=C(C([H])=C1[H])C(=O)C([H])([H])[H])C([H])([H])[H]	1275.8	Standard non polar	33892256
4-Hydroxy-3-methylacetophenone	[H]OC1=C(C([H])=C(C([H])=C1[H])C(=O)C([H])([H])[H])C([H])([H])[H]	1218.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methylacetophenone,1TMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C)C(C)=C1	1529.8	Semi standard non polar	33892256
4-Hydroxy-3-methylacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(C)=C1	1792.1	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 - 4-Hydroxy-3-methylacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pbi-3900000000-9c038162198f68e9fbcd	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methylacetophenone GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-7970000000-e793431297d2c47b3b69	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methylacetophenone 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 - 4-Hydroxy-3-methylacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-ed83600c70888f455b65	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 20V, Positive-QTOF	splash10-0udi-0900000000-6d0b9b55bb9468bc58e6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 40V, Positive-QTOF	splash10-057i-9600000000-12944568eb965fa1caed	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 10V, Negative-QTOF	splash10-0002-0900000000-3e68d6dc1d3bc39c73bc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 20V, Negative-QTOF	splash10-0002-0900000000-67145e9fb157501be8dc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 40V, Negative-QTOF	splash10-0a4l-7900000000-9077f4012e18e41b9f4b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 10V, Negative-QTOF	splash10-0002-0900000000-e0b12c10ffeec106d759	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 20V, Negative-QTOF	splash10-0002-1900000000-3f0725541cd3b32bbb70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 40V, Negative-QTOF	splash10-0006-9200000000-70163cf31ad1f4b6c157	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 10V, Positive-QTOF	splash10-0udi-1900000000-1b8ecd054743887d48a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 20V, Positive-QTOF	splash10-053u-4900000000-e825aa01a2fbe72cd961	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methylacetophenone 40V, Positive-QTOF	splash10-002f-9100000000-f3baa647d0cc9f697c28	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70135

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

Not Available

Showing metabocard for 4-Hydroxy-3-methylacetophenone (HMDB0059824)

MOL for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

3D MOL for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

3D SDF for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

3D-SDF for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

PDB for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

3D PDB for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

SMILES for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

INCHI for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

Structure for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

3D Structure for HMDB0059824 (4-Hydroxy-3-methylacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra