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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:17:30 UTC

Update Date

2022-09-22 18:35:02 UTC

HMDB ID

HMDB0341139

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bufexamac

Description

Bufexamac, also known as bufexamic acid or anderm, belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids. Bufexamac is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004221604442D          

 16 16  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 13 15  1  4  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341139

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCOC1=CC=C(CC(O)=NO)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO3/c1-2-3-8-16-11-6-4-10(5-7-11)9-12(14)13-15/h4-7,15H,2-3,8-9H2,1H3,(H,13,14)

> <INCHI_KEY>
MXJWRABVEGLYDG-UHFFFAOYSA-N

> <FORMULA>
C12H17NO3

> <MOLECULAR_WEIGHT>
223.272

> <EXACT_MASS>
223.120843411

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.350957424610392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-hydroxy2-(4-butoxyphenyl)ethanimidic acid

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.7867016403333333

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.589282961938682

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.535046256451295

> <JCHEM_PKA_STRONGEST_BASIC>
0.3947210826969536

> <JCHEM_POLAR_SURFACE_AREA>
62.05000000000001

> <JCHEM_REFRACTIVITY>
61.81090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
jomax

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      17.338  -3.850   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      16.004  -1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      18.672  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    3   16                                                       
CONECT    9   10   12                                                       
CONECT   10    4    5    9                                                  
CONECT   11    6    7   16                                                  
CONECT   12    9   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13                                                            
CONECT   16    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(p-Butoxyphenyl)-acetohydroxamic acid	ChEBI
4-Butoxy-N-hydroxybenzeneacetamide	ChEBI
4-Butoxyphenylacetohydroxamic acid	ChEBI
Acide p-butoxyphenylacethydroxamique	ChEBI
Bufexamaco	ChEBI
Bufexamacum	ChEBI
Bufexamic acid	ChEBI
p-Butoxyphenylacetohydroxamic acid	ChEBI
Anderm	Kegg
2-(p-Butoxyphenyl)-acetohydroxamate	Generator
4-Butoxyphenylacetohydroxamate	Generator
Bufexamate	Generator
p-Butoxyphenylacetohydroxamate	Generator
Allergipuran	MeSH
Bioglan brand OF bufexamac	MeSH
Bufexamac scheurich brand	MeSH
Sanofi synthelabo brand OF bufexamac	MeSH
Whitehall brand OF bufexamac	MeSH
Windol	MeSH
AHP brand OF bufexamac	MeSH
Bufexamac-ratiopharm	MeSH
Droxaryl	MeSH
Malipuran	MeSH
Scheurich brand OF bufexamac	MeSH
P Butoxyphenylacethydroxamic acid	MeSH
Merck dura brand OF bufexamac	MeSH
Bufexamac dermapharm brand	MeSH
Bufexamac galenpharma brand	MeSH
Bufexamac ratiopharm	MeSH
Pfizer brand OF bufexamac	MeSH
Bufexamac	MeSH
Bufal	MeSH
Bufederm	MeSH
Bufexamac ratiopharm brand	MeSH
Dermapharm brand OF bufexamac	MeSH
Jomax	MeSH
Paraderm	MeSH
P-Butoxyphenylacethydroxamic acid	MeSH
Bufexamac ahp brand	MeSH
Bufexamac pfizer brand	MeSH
Pierre fabre brand OF bufexamac	MeSH
Bufexamac bioglan brand	MeSH
Bufexamac whitehall brand	MeSH
Bufexamacratiopharm	MeSH
GALENpharma brand OF bufexamac	MeSH
Parfenac	MeSH
Duradermal	MeSH
Ratiopharm brand OF bufexamac	MeSH

Chemical Formula

C₁₂H₁₇NO₃

Average Molecular Weight

223.272

Monoisotopic Molecular Weight

223.120843411

IUPAC Name

N-hydroxy2-(4-butoxyphenyl)ethanimidic acid

Traditional Name

jomax

CAS Registry Number

Not Available

SMILES

CCCCOC1=CC=C(CC(O)=NO)C=C1

InChI Identifier

InChI=1S/C12H17NO3/c1-2-3-8-16-11-6-4-10(5-7-11)9-12(14)13-15/h4-7,15H,2-3,8-9H2,1H3,(H,13,14)

InChI Key

MXJWRABVEGLYDG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetamides

Direct Parent

Phenylacetamides

Alternative Parents

Substituents

Phenylacetamide
Phenoxy compound
Phenol ether
Alkyl aryl ether
Hydroxamic acid
Carboxylic acid derivative
Ether
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:31317 )
hydroxamic acid (CHEBI:31317 )

Ontology

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	2.5	ALOGPS
logP	2.79	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.54	ChemAxon
pKa (Strongest Basic)	0.39	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.81 m³·mol⁻¹	ChemAxon
Polarizability	24.35 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 Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , negative-QTOF	splash10-00di-1090000000-f24ae0d85b1376dd6695	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , negative-QTOF	splash10-00di-5390000000-1064111002b4036cfbbb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , negative-QTOF	splash10-0aor-7900000000-789660a43653a49880b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , negative-QTOF	splash10-066r-5900000000-91ae318ee7bf4a0c8ebb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , negative-QTOF	splash10-014i-4900000000-15c66804db050221c331	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , negative-QTOF	splash10-014i-3900000000-a41498b64629a3eda39c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-qTof , Positive-QTOF	splash10-08mi-0920000000-e2854ce6292c5d0a1c8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-qTof , Positive-QTOF	splash10-0a4i-4910100000-7ff98d442e9aa0a2f64d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , positive-QTOF	splash10-03di-0920000000-9e2d982e08339f818cf6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , positive-QTOF	splash10-0bt9-0900000000-435c1f72113403e534fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , positive-QTOF	splash10-0a4i-0900000000-9de68224c670d85b5621	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , positive-QTOF	splash10-0a4i-0900000000-496edd1f1dfb18e3bc93	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , positive-QTOF	splash10-0a4i-1900000000-3e269c82012ba53557c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac LC-ESI-QFT , positive-QTOF	splash10-0a4i-2900000000-80c7b8b429b26dfbbfc6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac , positive-QTOF	splash10-08mi-0920000000-e2854ce6292c5d0a1c8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bufexamac , positive-QTOF	splash10-0a4i-4910100000-7ff98d442e9aa0a2f64d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufexamac 10V, Negative-QTOF	splash10-00di-2790000000-a888ce6056e5f170d8f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufexamac 20V, Negative-QTOF	splash10-0cdm-7920000000-844caa547238084d9a5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufexamac 40V, Negative-QTOF	splash10-052b-7900000000-dd69ba5273b008ba5b9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufexamac 10V, Positive-QTOF	splash10-00di-3790000000-4039782277746e9f762f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufexamac 20V, Positive-QTOF	splash10-0bt9-3910000000-1551e839edb87240079d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufexamac 40V, Positive-QTOF	splash10-0a4i-9300000000-0b2e57d6765bd1d7de8e	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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 Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13346

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

Bufexamac

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

31317

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

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for Bufexamac (HMDB0341139)

MOL for HMDB0341139 (Bufexamac)

3D MOL for HMDB0341139 (Bufexamac)

3D SDF for HMDB0341139 (Bufexamac)

3D-SDF for HMDB0341139 (Bufexamac)

PDB for HMDB0341139 (Bufexamac)

3D PDB for HMDB0341139 (Bufexamac)

SMILES for HMDB0341139 (Bufexamac)

INCHI for HMDB0341139 (Bufexamac)

Structure for HMDB0341139 (Bufexamac)

3D Structure for HMDB0341139 (Bufexamac)

Predicted Kovats Retention Indices

MS/MS Spectra