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Showing metabocard for (R)-Menthofuran (HMDB0036089)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:09:27 UTC
Update Date2023-02-21 17:25:03 UTC
HMDB IDHMDB0036089
Secondary Accession Numbers
  • HMDB36089
Metabolite Identification
Common Name(R)-Menthofuran
Description(R)-Menthofuran belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on (R)-Menthofuran.
Structure
Data?1677000303
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0036089 ((R)-Menthofuran)


  Mrv0541 05061308532D          

 11 12  0  0  0  0            999 V2000
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0036089 ((R)-Menthofuran)

HMDB0036089
     RDKit          3D
(R)-Menthofuran
 25 26  0  0  0  0  0  0  0  0999 V2000
   -3.2101   -0.9020    0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2307    0.1581   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4304    1.4928   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    2.0588   -0.4952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958    1.2155   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607    0.0121    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281   -1.1497    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848   -0.6076    1.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618    0.3542    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709   -0.4362   -0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    1.4449   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -1.4148   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548   -1.6613    0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0657   -0.4523    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4370    1.8994   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2914   -1.6064   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5576   -1.8913    0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -0.0459    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8740   -1.3797    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7305    0.8221    0.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -1.3393   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300    0.1617   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -0.7770   -0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4538    1.6184   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3652    2.4258    0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  6  2  1  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
M  END
Download

3D SDF for HMDB0036089 ((R)-Menthofuran)


  Mrv0541 05061308532D          

 11 12  0  0  0  0            999 V2000
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036089

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2=C(C1)OC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3

> <INCHI_KEY>
YGWKXXYGDYYFJU-UHFFFAOYSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.2176

> <EXACT_MASS>
150.10446507

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
18.03804916942848

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
3.130279691666666

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4425252184058337

> <JCHEM_POLAR_SURFACE_AREA>
13.14

> <JCHEM_REFRACTIVITY>
45.6749

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,9-epoxy-p-mentha-3,8-diene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0036089 ((R)-Menthofuran)

HMDB0036089
     RDKit          3D
(R)-Menthofuran
 25 26  0  0  0  0  0  0  0  0999 V2000
   -3.2101   -0.9020    0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2307    0.1581   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4304    1.4928   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    2.0588   -0.4952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958    1.2155   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607    0.0121    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281   -1.1497    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848   -0.6076    1.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618    0.3542    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709   -0.4362   -0.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    1.4449   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021   -1.4148   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548   -1.6613    0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0657   -0.4523    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4370    1.8994   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2914   -1.6064   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5576   -1.8913    0.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -0.0459    1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8740   -1.3797    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7305    0.8221    0.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -1.3393   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300    0.1617   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -0.7770   -0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4538    1.6184   -1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3652    2.4258    0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  6  2  1  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
M  END
Download

PDB for HMDB0036089 ((R)-Menthofuran)

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       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    4    7                                                       
CONECT    4    3    9                                                       
CONECT    5    7   10                                                       
CONECT    6    8   11                                                       
CONECT    7    1    3    5                                                  
CONECT    8    2    6    9                                                  
CONECT    9    4    8   10                                                  
CONECT   10    5    9   11                                                  
CONECT   11    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0036089 ((R)-Menthofuran)

COMPND    HMDB0036089
HETATM    1  C1  UNL     1      -3.210  -0.902   0.282  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.231   0.158  -0.003  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.430   1.493  -0.328  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.278   2.059  -0.495  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.296   1.215  -0.310  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.861   0.012   0.001  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.028  -1.150   0.268  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.185  -0.608   1.054  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.962   0.354   0.208  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.771  -0.436  -0.799  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.162   1.445  -0.401  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.502  -1.415  -0.654  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.755  -1.661   0.955  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.066  -0.452   0.816  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.437   1.899  -0.405  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.291  -1.606  -0.685  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.558  -1.891   0.848  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.781  -0.046   1.916  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.874  -1.380   1.427  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.730   0.822   0.893  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.257  -1.339  -1.158  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.030   0.162  -1.700  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.732  -0.777  -0.351  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.454   1.618  -1.475  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.365   2.426   0.099  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    6
CONECT    3    4   15
CONECT    4    5
CONECT    5    6    6   11
CONECT    6    7
CONECT    7    8   16   17
CONECT    8    9   18   19
CONECT    9   10   11   20
CONECT   10   21   22   23
CONECT   11   24   25
END
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SMILES for HMDB0036089 ((R)-Menthofuran)

CC1CCC2=C(C1)OC=C2C
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INCHI for HMDB0036089 ((R)-Menthofuran)

InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3,9-Epoxy-p-mentha-3,8-dieneChEBI
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuranChEBI
4,5,6,7-Tetrahydro-3,6-dimethylcoumaroneChEBI
(+)-3,9-Epoxy-P-mentha-3,8-dieneHMDB
(+)-MenthofuranHMDB
(6R)-3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuranHMDB
(R)-(+)-MenthofuranHMDB
(R)-4,5,6,7-tetrahydro-3,6-DimethylbenzofuranHMDB
3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuranHMDB
3,9-Epoxy-(+)-P-mentha-3,8-dieneHMDB
4,5,6,7-tetrahydro-3,6-Dimethyl-(R)-benzofuranHMDB
4,5,6,7-tetrahydro-3,6-Dimethyl-benzofuranHMDB
MenthofuranHMDB
Menthofuran, (R)-isomerMeSH, HMDB
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Traditional Name3,9-epoxy-p-mentha-3,8-diene
CAS Registry Number17957-94-7
SMILES
CC1CCC2=C(C1)OC=C2C
InChI Identifier
InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3
InChI KeyYGWKXXYGDYYFJU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Menthofuran monoterpenoid
  • Bicyclic monoterpenoid
  • Aromatic monoterpenoid
  • Benzofuran
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point86.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point80.00 to 82.00 °C. @ 13.00 mm HgThe Good Scents Company Information System
Water Solubility16.36 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.562 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP3.98ALOGPS
logP3.13ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.67 m³·mol⁻¹ChemAxon
Polarizability18.04 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.92931661259
DarkChem[M-H]-128.73231661259
DeepCCS[M+H]+134.7830932474
DeepCCS[M-H]-131.69230932474
DeepCCS[M-2H]-168.81630932474
DeepCCS[M+Na]+143.91730932474
AllCCS[M+H]+130.832859911
AllCCS[M+H-H2O]+126.132859911
AllCCS[M+NH4]+135.232859911
AllCCS[M+Na]+136.432859911
AllCCS[M-H]-135.832859911
AllCCS[M+Na-2H]-136.932859911
AllCCS[M+HCOO]-138.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.25 minutes32390414
Predicted by Siyang on May 30, 202218.5616 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.77 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1960.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid714.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid271.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid470.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid378.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid705.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid870.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)413.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1514.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid607.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1773.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid529.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid472.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate563.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA600.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water22.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-MenthofuranCC1CCC2=C(C1)OC=C2C1510.1Standard polar33892256
(R)-MenthofuranCC1CCC2=C(C1)OC=C2C1131.3Standard non polar33892256
(R)-MenthofuranCC1CCC2=C(C1)OC=C2C1163.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (R)-Menthofuran EI-B (Non-derivatized)splash10-0a4i-4900000000-ad7d24da86fd955477a72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-Menthofuran EI-B (Non-derivatized)splash10-0a4i-4900000000-ad7d24da86fd955477a72018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Menthofuran GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi9-1900000000-c7d34068fe20520e5e882017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Menthofuran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Menthofuran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Positive-QTOFsplash10-0udi-0900000000-295d2c3abad7c8ff4f632015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Positive-QTOFsplash10-0udi-3900000000-5e060ac38ef1d423776f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Positive-QTOFsplash10-0gb9-9100000000-30417e50d66ad0fe9af62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Positive-QTOFsplash10-0udi-0900000000-295d2c3abad7c8ff4f632015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Positive-QTOFsplash10-0udi-3900000000-5e060ac38ef1d423776f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Positive-QTOFsplash10-0gb9-9100000000-30417e50d66ad0fe9af62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Negative-QTOFsplash10-0002-0900000000-881d258a03659e0f39302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Negative-QTOFsplash10-0002-0900000000-01ff41b309657177e5e52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Negative-QTOFsplash10-066r-3900000000-177076fd487978d174f12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Negative-QTOFsplash10-0002-0900000000-881d258a03659e0f39302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Negative-QTOFsplash10-0002-0900000000-01ff41b309657177e5e52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Negative-QTOFsplash10-066r-3900000000-177076fd487978d174f12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Positive-QTOFsplash10-0udi-1900000000-a36c450a85a702daacb32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Positive-QTOFsplash10-0zfs-9800000000-283087fbd503dd3860782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Positive-QTOFsplash10-002f-9100000000-bb914f0c52d327a80b1b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 10V, Negative-QTOFsplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 20V, Negative-QTOFsplash10-0002-0900000000-8ae160b4249f862d1a002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Menthofuran 40V, Negative-QTOFsplash10-05ne-7900000000-12e4673f2e9f1e3c406d2021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014927
KNApSAcK IDC00003049
Chemspider ID292309
KEGG Compound IDC09868
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMenthofuran
METLIN IDNot Available
PubChem Compound329983
PDB IDNot Available
ChEBI ID50542
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1019781
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  2. Thomassen D, Slattery JT, Nelson SD: Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. J Pharmacol Exp Ther. 1988 Mar;244(3):825-9. [PubMed:3252034 ]
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  4. Chen LJ, Lebetkin EH, Burka LT: Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. Drug Metab Dispos. 2003 Oct;31(10):1208-13. [PubMed:12975329 ]
  5. Stephens ES, Walsh AA, Scott EE: Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes. Drug Metab Dispos. 2012 Sep;40(9):1797-802. doi: 10.1124/dmd.112.045161. Epub 2012 Jun 13. [PubMed:22696418 ]
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  7. Khojasteh-Bakht SC, Nelson SD, Atkins WM: Glutathione S-transferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones. Arch Biochem Biophys. 1999 Oct 1;370(1):59-65. [PubMed:10496977 ]
  8. Haigou R, Miyazawa M: Metabolism of (+)-terpinen-4-ol by cytochrome P450 enzymes in human liver microsomes. J Oleo Sci. 2012;61(1):35-43. [PubMed:22188805 ]
  9. Atsbaha Zebelo S, Bertea CM, Bossi S, Occhipinti A, Gnavi G, Maffei ME: Chrysolina herbacea modulates terpenoid biosynthesis of Mentha aquatica L. PLoS One. 2011 Mar 9;6(3):e17195. doi: 10.1371/journal.pone.0017195. [PubMed:21408066 ]
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  11. Khojasteh-Bakht SC, Koenigs LL, Peter RM, Trager WF, Nelson SD: (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Drug Metab Dispos. 1998 Jul;26(7):701-4. [PubMed:9660853 ]
  12. Khojasteh-Bakht SC, Chen W, Koenigs LL, Peter RM, Nelson SD: Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide. Drug Metab Dispos. 1999 May;27(5):574-80. [PubMed:10220485 ]
  13. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  14. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  15. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
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