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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:15 UTC

Update Date

2023-02-21 17:21:56 UTC

HMDB ID

HMDB0032336

Secondary Accession Numbers

HMDB32336

Metabolite Identification

Common Name

3-Hydroxy-4-phenylbutan-2-one

Description

3-Hydroxy-4-phenylbutan-2-one, also known as 2-butanone, 3-hydroxy-4-phenyl or 4-phenyl-3-hydroxybutan-2-one, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Based on a literature review very few articles have been published on 3-Hydroxy-4-phenylbutan-2-one.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7    9   10                                                       
CONECT    8    1   10   11                                                  
CONECT    9    5    6    7                                                  
CONECT   10    7    8   12                                                  
CONECT   11    8                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Butanone, 3-hydroxy-4-phenyl	HMDB
4-Phenyl-3-hydroxybutan-2-one	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

3-hydroxy-4-phenylbutan-2-one

Traditional Name

3-hydroxy-4-phenylbutan-2-one

CAS Registry Number

5355-63-5

SMILES

CC(=O)C(O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C10H12O2/c1-8(11)10(12)7-9-5-3-2-4-6-9/h2-6,10,12H,7H2,1H3

InChI Key

QBCUUJGHWFKMDC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Acyloin
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032336)
Cytoplasm (HMDB: HMDB0032336)

Source

Endogenous

Endogenous (HMDB: HMDB0032336)

Exogenous

Food

Food (HMDB: HMDB0032336)

Exogenous (HMDB: HMDB0032336)

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	5.58 g/L	ALOGPS
logP	0.98	ALOGPS
logP	1.51	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	13.33	ChemAxon
pKa (Strongest Basic)	-3.5	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	3	ChemAxon
Refractivity	47.01 m³·mol⁻¹	ChemAxon
Polarizability	17.81 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
DarkChem	[M+H]+	136.635	31661259
DarkChem	[M-H]-	131.54	31661259
DeepCCS	[M+H]+	133.883	30932474
DeepCCS	[M-H]-	131.053	30932474
DeepCCS	[M-2H]-	167.246	30932474
DeepCCS	[M+Na]+	142.67	30932474
AllCCS	[M+H]+	136.1	32859911
AllCCS	[M+H-H2O]+	131.7	32859911
AllCCS	[M+NH4]+	140.2	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	136.7	32859911
AllCCS	[M+Na-2H]-	137.8	32859911
AllCCS	[M+HCOO]-	139.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4-phenylbutan-2-one	CC(=O)C(O)CC1=CC=CC=C1	2237.5	Standard polar	33892256
3-Hydroxy-4-phenylbutan-2-one	CC(=O)C(O)CC1=CC=CC=C1	1316.5	Standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one	CC(=O)C(O)CC1=CC=CC=C1	1353.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4-phenylbutan-2-one,1TMS,isomer #1	CC(=O)C(CC1=CC=CC=C1)O[Si](C)(C)C	1426.1	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,1TMS,isomer #2	CC(O[Si](C)(C)C)=C(O)CC1=CC=CC=C1	1564.9	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,1TMS,isomer #3	C=C(O[Si](C)(C)C)C(O)CC1=CC=CC=C1	1441.3	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,2TMS,isomer #1	CC(O[Si](C)(C)C)=C(CC1=CC=CC=C1)O[Si](C)(C)C	1600.7	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,2TMS,isomer #1	CC(O[Si](C)(C)C)=C(CC1=CC=CC=C1)O[Si](C)(C)C	1613.2	Standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(CC1=CC=CC=C1)O[Si](C)(C)C	1492.9	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,2TMS,isomer #2	C=C(O[Si](C)(C)C)C(CC1=CC=CC=C1)O[Si](C)(C)C	1599.9	Standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,1TBDMS,isomer #1	CC(=O)C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1669.0	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,1TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C(O)CC1=CC=CC=C1	1811.9	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)C(O)CC1=CC=CC=C1	1673.3	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2057.3	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2019.2	Standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1963.4	Semi standard non polar	33892256
3-Hydroxy-4-phenylbutan-2-one,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2007.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-d9ff230ad8227dc09f8f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9400000000-0387fd331cb4da681111	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 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 - 3-Hydroxy-4-phenylbutan-2-one 10V, Positive-QTOF	splash10-014j-0900000000-87ba6264b385da4a4371	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 20V, Positive-QTOF	splash10-00kb-5900000000-eee31f6b3f93199787a5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 40V, Positive-QTOF	splash10-002f-9300000000-c7a29e18aa616a733c2a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 10V, Negative-QTOF	splash10-03di-1900000000-609dcbe4c5a60d549fb6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 20V, Negative-QTOF	splash10-02ml-4900000000-e644257bd3f96137fdbb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 40V, Negative-QTOF	splash10-0006-9300000000-4b4f7e92df5cff520b70	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 10V, Negative-QTOF	splash10-03di-3900000000-41261ce8c11c78004423	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 20V, Negative-QTOF	splash10-0006-9000000000-8e87b2544a6e8cef4779	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 40V, Negative-QTOF	splash10-0006-9200000000-e5489837cad018fa78df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 10V, Positive-QTOF	splash10-0096-8900000000-43b81600100235971366	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 20V, Positive-QTOF	splash10-0006-9200000000-828db0951cfecbbc1e2c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 40V, Positive-QTOF	splash10-0006-9100000000-0cbe88a7f712999d760f	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Cytoplasm
Extracellular

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

FDB009609

KNApSAcK ID

Not Available

Chemspider ID

4934307

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6428929

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

(). EAFUS: Everything Added to Food in the United States.. .

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

3-Hydroxy-4-phenylbutan-2-one → [(3-oxo-1-phenylbutan-2-yl)oxy]sulfonic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

3-Hydroxy-4-phenylbutan-2-one → 3,4,5-trihydroxy-6-[(3-oxo-1-phenylbutan-2-yl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for 3-Hydroxy-4-phenylbutan-2-one (HMDB0032336)

MOL for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

3D MOL for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

3D SDF for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

3D-SDF for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

PDB for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

3D PDB for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

SMILES for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

INCHI for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

Structure for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

3D Structure for HMDB0032336 (3-Hydroxy-4-phenylbutan-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions