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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-21 06:14:14 UTC

Update Date

2023-02-21 17:30:51 UTC

HMDB ID

HMDB0062402

Secondary Accession Numbers

HMDB62402

Metabolite Identification

Common Name

4-Hydroxy-1-(3-pyridinyl)-1-butanone

Description

4-Hydroxy-1-(3-pyridinyl)-1-butanone, also known as 4-HPB, belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 4-Hydroxy-1-(3-pyridinyl)-1-butanone is a strong basic compound (based on its pKa). 4-Hydroxy-1-(3-pyridinyl)-1-butanone is a potentially toxic compound.

Structure

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

HEADER    PROTEIN                                 07-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-14         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    8                                                       
CONECT    4    2    9                                                       
CONECT    5    1   10                                                       
CONECT    6    2   11                                                       
CONECT    7    8   10                                                       
CONECT    8    3    7    9                                                  
CONECT    9    4    8   12                                                  
CONECT   10    5    7                                                       
CONECT   11    6                                                            
CONECT   12    9                                                            
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
4-Hydoxy-1-(3-pyridyl)-1-butanone	HMDB
4-HPB	HMDB

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

4-hydroxy-1-(pyridin-3-yl)butan-1-one

Traditional Name

4-hydroxy-1-(pyridin-3-yl)butan-1-one

CAS Registry Number

59578-62-0

SMILES

OCCCC(=O)C1=CN=CC=C1

InChI Identifier

InChI=1S/C9H11NO2/c11-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,11H,2,4,6H2

InChI Key

KTXUGZHJVRHQGP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Pyridine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ketone (CHEBI:82563 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0062402)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (HMDB: HMDB0062402)

Biochemical pathway

Physiological pathway

Base excision repair (HMDB: HMDB0062402)

Disease pathway

Anticonvulsants (HMDB: HMDB0062402)

Metabolic pathway

Nucleotide excision repair (HMDB: HMDB0062402)

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	34.8 g/l	ALOGPS
LogP	0.01	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.01	ALOGPS
logP	0.022	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	15.05	ChemAxon
pKa (Strongest Basic)	3.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	45.46 m³·mol⁻¹	ChemAxon
Polarizability	17.58 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	136.48	31661259
DarkChem	[M-H]-	135.143	31661259
DeepCCS	[M+H]+	136.608	30932474
DeepCCS	[M-H]-	132.778	30932474
DeepCCS	[M-2H]-	170.426	30932474
DeepCCS	[M+Na]+	145.965	30932474
AllCCS	[M+H]+	135.7	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	139.8	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	138.0	32859911
AllCCS	[M+HCOO]-	139.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-1-(3-pyridinyl)-1-butanone	OCCCC(=O)C1=CN=CC=C1	2195.4	Standard polar	33892256
4-Hydroxy-1-(3-pyridinyl)-1-butanone	OCCCC(=O)C1=CN=CC=C1	1564.5	Standard non polar	33892256
4-Hydroxy-1-(3-pyridinyl)-1-butanone	OCCCC(=O)C1=CN=CC=C1	1610.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-1-(3-pyridinyl)-1-butanone,1TMS,isomer #1	C[Si](C)(C)OCCCC(=O)C1=CC=CN=C1	1669.6	Semi standard non polar	33892256
4-Hydroxy-1-(3-pyridinyl)-1-butanone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCC(=O)C1=CC=CN=C1	1899.3	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 - 4-Hydroxy-1-(3-pyridinyl)-1-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-1d69cae726aabf1a1626	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-6900000000-de673401d11393d3ee69	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 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-1-(3-pyridinyl)-1-butanone 10V, Positive-QTOF	splash10-00kb-0900000000-f49142ef3f7d1a71dd5c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 20V, Positive-QTOF	splash10-0002-4900000000-30131ee6b868ce84fdda	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 40V, Positive-QTOF	splash10-0536-9400000000-2447d8d61ceebbc3970a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 10V, Negative-QTOF	splash10-03di-0900000000-98c52d3e909d15016e8d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 20V, Negative-QTOF	splash10-03di-2900000000-1f70a4b9bf9cb80166f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 40V, Negative-QTOF	splash10-004l-9300000000-12a7c2e33732063d597c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 10V, Negative-QTOF	splash10-03di-2900000000-a8b302c48b6b0ed1dc10	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 20V, Negative-QTOF	splash10-004i-9400000000-6303587fcc08df66c63e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 40V, Negative-QTOF	splash10-004i-9400000000-ac340138c7eadea045da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 10V, Positive-QTOF	splash10-00xr-1900000000-c1364b13ecb7dfef59b5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 20V, Positive-QTOF	splash10-00dl-5900000000-1c253bf34b80bdf230d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-1-(3-pyridinyl)-1-butanone 40V, Positive-QTOF	splash10-0059-9200000000-495fdca0cb893d74588e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

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

C19565

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107819

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

M00985

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-1-(3-pyridinyl)-1-butanone (HMDB0062402)

MOL for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

3D MOL for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

3D SDF for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

3D-SDF for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

PDB for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

3D PDB for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

SMILES for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

INCHI for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

Structure for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

3D Structure for HMDB0062402 (4-Hydroxy-1-(3-pyridinyl)-1-butanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra