Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:17:48 UTC

Update Date

2022-09-22 18:35:02 UTC

HMDB ID

HMDB0341140

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Butenafine HCl

Description

butenafine hydrochloride, also known as butenafine HCL or mentax, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. butenafine hydrochloride is a drug. butenafine hydrochloride is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 08221314092D          

 25 26  0  0  0  0            999 V2000
    3.3044   -2.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0025   -1.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1775   -3.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4465    0.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1258    2.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1258    1.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2679    2.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4113    2.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9824    2.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2679    1.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4113    1.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4465   -2.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -0.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8755   -1.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2679   -0.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9824    0.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4465   -1.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    2.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9824    1.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8755   -2.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    1.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5900   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2679   -0.0172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5437    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 18 12  2  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
 19  8  2  0  0  0  0
 19  9  1  0  0  0  0
 20 10  2  0  0  0  0
 20 17  1  0  0  0  0
 21 14  2  0  0  0  0
 21 15  1  0  0  0  0
 22 11  2  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 23  3  1  0  0  0  0
 23 21  1  0  0  0  0
 24  4  1  0  0  0  0
 24 16  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341140

> <DATABASE_NAME>
hmdb

> <SMILES>
Cl.CN(CC1=CC=C(C=C1)C(C)(C)C)CC1=CC=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C23H27N.ClH/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20;/h5-15H,16-17H2,1-4H3;1H

> <INCHI_KEY>
LJBSAUIFGPSHCN-UHFFFAOYSA-N

> <FORMULA>
C23H28ClN

> <MOLECULAR_WEIGHT>
353.928

> <EXACT_MASS>
353.191027608

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
38.69959670382633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine hydrochloride

> <ALOGPS_LOGP>
5.85

> <JCHEM_LOGP>
6.173648727666666

> <ALOGPS_LOGS>
-6.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.233430737971924

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
104.32939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.56e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butenafine hydrochloride

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-AUG-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-13         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   25 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7    9   10                                                       
CONECT    8    5   19                                                       
CONECT    9    7   19                                                       
CONECT   10    7   20                                                       
CONECT   11    6   22                                                       
CONECT   12   14   18                                                       
CONECT   13   15   18                                                       
CONECT   14   12   21                                                       
CONECT   15   13   21                                                       
CONECT   16   18   24                                                       
CONECT   17   20   24                                                       
CONECT   18   12   13   16                                                  
CONECT   19    8    9   22                                                  
CONECT   20   10   17   22                                                  
CONECT   21   14   15   23                                                  
CONECT   22   11   19   20                                                  
CONECT   23    1    2    3   21                                             
CONECT   24    4   16   17                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4-Tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanaminium chloride	ChEBI
4-Tert-butylbenzyl(methyl)(1-naphthalenemethyl)amine hydrochloride	ChEBI
Butenafine HCL	ChEBI
N-(p-Tert-butylbenzyl)-N-methyl-1-naphthalenemethylamine hydrochloride	ChEBI
Mentax	Kegg
Volley	Kegg
N-4-Tert-butylbenzyl-N-methyl-1-naphthalene methylamine hydrochloride	MeSH
Butenafine	MeSH

Chemical Formula

C₂₃H₂₈ClN

Average Molecular Weight

353.928

Monoisotopic Molecular Weight

353.191027608

IUPAC Name

[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine hydrochloride

Traditional Name

butenafine hydrochloride

CAS Registry Number

Not Available

SMILES

Cl.CN(CC1=CC=C(C=C1)C(C)(C)C)CC1=CC=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C23H27N.ClH/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20;/h5-15H,16-17H2,1-4H3;1H

InChI Key

LJBSAUIFGPSHCN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Phenylpropane
Phenylmethylamine
Benzylamine
Aralkylamine
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Hydrochloride
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

ammonium salt (CHEBI:31325 )
hydrochloride (CHEBI:31325 )

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	5.85	ALOGPS
logP	6.17	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.33 m³·mol⁻¹	ChemAxon
Polarizability	38.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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 - Butenafine HCl , positive-QTOF	splash10-014l-0906000000-3459e9006c906bb4c741	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butenafine HCl 10V, Positive-QTOF	splash10-0udi-0009000000-eabf1473f9ec6bed5eea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butenafine HCl 20V, Positive-QTOF	splash10-0udi-0009000000-eabf1473f9ec6bed5eea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butenafine HCl 40V, Positive-QTOF	splash10-0udi-0009000000-eabf1473f9ec6bed5eea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butenafine HCl 10V, Negative-QTOF	splash10-0udi-0009000000-90e1fd50405236ef0560	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butenafine HCl 20V, Negative-QTOF	splash10-0udi-0009000000-90e1fd50405236ef0560	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butenafine HCl 40V, Negative-QTOF	splash10-0udi-0009000000-90e1fd50405236ef0560	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

DBSALT000245

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C12490

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butenafine

METLIN ID

Not Available

PubChem Compound

443867

PDB ID

Not Available

ChEBI ID

31325

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 Butenafine HCl (HMDB0341140)

MOL for HMDB0341140 (Butenafine HCl)

3D MOL for HMDB0341140 (Butenafine HCl)

3D SDF for HMDB0341140 (Butenafine HCl)

3D-SDF for HMDB0341140 (Butenafine HCl)

PDB for HMDB0341140 (Butenafine HCl)

3D PDB for HMDB0341140 (Butenafine HCl)

SMILES for HMDB0341140 (Butenafine HCl)

INCHI for HMDB0341140 (Butenafine HCl)

Structure for HMDB0341140 (Butenafine HCl)

3D Structure for HMDB0341140 (Butenafine HCl)

Predicted Kovats Retention Indices

MS/MS Spectra