Np mrd loader

Showing NP-Card for Menthofuran (NP0048448)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-17 20:56:38 UTC
Updated at2022-03-17 20:56:38 UTC
NP-MRD IDNP0048448
Secondary Accession NumbersNone
Natural Product Identification
Common NameMenthofuran
Description(R)-Menthofuran belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring (R)-Menthofuran is an extremely weak basic (essentially neutral) compound (based on its pKa) (R)-Menthofuran is a coffee, earthy, and musty tasting compound. Outside of the human body, (R)-Menthofuran has been detected, but not quantified in, a few different foods, such as herbs and spices, mentha (mint), and orange mints. This could make (R)-menthofuran a potential biomarker for the consumption of these foods. Menthofuran is found in Agathosma betulina, Clinopodium ashei, Clinopodium serpyllifolium, Cunila microcephala, Curcuma longa, Euodia hortensis, Mentha longifolia, Mentha piperita, Mentha piperita L. , Mentha pulegium, Mentha spp. , Mentha verticillata, Methanothermobacter thermautotrophicus, Minthostachys andina and Pycnanthemum floridanum. Menthofuran was first documented in 1988 (PMID: 3252034). A monoterpenoid that is 4,5,6,7-tetrahydro-1-benzofuran substituted by methyl groups at positions 3 and 6 (PMID: 18044925) (PMID: 23199997) (PMID: 24050256) (PMID: 22054099).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048448 (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 NP0048448 (Menthofuran)

Download
3D SDF for NP0048448 (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>
NP0048448

> <DATABASE_NAME>
NP-MRD

> <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 NP0048448 (Menthofuran)
Download
PDB for NP0048448 (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

Download
3D PDB for NP0048448 (Menthofuran)
Download
SMILES for NP0048448 (Menthofuran)
CC1CCC2=C(C1)OC=C2C
Download
INCHI for NP0048448 (Menthofuran)
InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3
Download
View in JSmol
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)-isomerHMDB
Chemical FormulaC10H14O
Average Mass150.2176 Da
Monoisotopic Mass150.10447 Da
IUPAC Name3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Traditional Name3,9-epoxy-p-mentha-3,8-diene
CAS Registry Number494-90-6
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agathosma betulinaLOTUS Database
Calamintha asheiLOTUS Database
Clinopodium serpyllifoliumLOTUS Database
Cunila microcephalaLOTUS Database
Curcuma longaLOTUS Database
Euodia hortensisLOTUS Database
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha longifoliaLOTUS Database
Mentha piperitaLOTUS Database
Mentha piperita L.Plant
Mentha pulegiumLOTUS Database
Mentha spicataFooDB
Mentha spp.Plant
Mentha verticillataLOTUS Database
Mentha x piperitaFooDB
Methanothermobacter thermautotrophicusLOTUS Database
Minthostachys andinaLOTUS Database
Pycnanthemum floridanumLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0036089  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. De Lucia M, Mainieri F, Verotta L, Maffei M, Panzella L, Crescenzi O, Napolitano A, Barone V, Appendino G, d'Ischia M: Nitration versus nitrosation chemistry of menthofuran: remarkable fragmentation and dimerization pathways and expeditious entry into dehydromenthofurolactone. J Org Chem. 2007 Dec 21;72(26):10123-9. doi: 10.1021/jo701992r. Epub 2007 Nov 29. [PubMed:18044925  ] 
  2. Tyagi AK, Gottardi D, Malik A, Guerzoni ME: Anti-yeast activity of mentha oil and vapours through in vitro and in vivo (real fruit juices) assays. Food Chem. 2013 Apr 15;137(1-4):108-14. doi: 10.1016/j.foodchem.2012.10.015. Epub 2012 Oct 26. [PubMed:23199997  ] 
  3. Caboni P, Saba M, Tocco G, Casu L, Murgia A, Maxia A, Menkissoglu-Spiroudi U, Ntalli N: Nematicidal activity of mint aqueous extracts against the root-knot nematode Meloidogyne incognita. J Agric Food Chem. 2013 Oct 16;61(41):9784-8. doi: 10.1021/jf403684h. Epub 2013 Oct 3. [PubMed:24050256  ] 
  4. Miyazawa M, Haigou R: Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes. Xenobiotica. 2011 Dec;41(12):1056-62. doi: 10.3109/00498254.2011.596230. [PubMed:22054099  ] 
  5. 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  ]