NP-MRD: Showing NP-Card for 8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one (NP0181082)

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Record Information

Version

2.0

Created at

2022-09-03 19:32:10 UTC

Updated at

2022-09-03 19:32:10 UTC

NP-MRD ID

NP0181082

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one

Description

Isoalantolactone, also known as isohelenin, belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Isoalantolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isoalantolactone has been detected, but not quantified in, herbs and spices. This could make isoalantolactone a potential biomarker for the consumption of these foods. Alantolactone occurs in the roots of Inula helenium and other Inula species. In 1895 the German scientists Julius Bredt and Wilhelm Posh extracted helenin from Inula helenium and determined its physical and chemical properties. Helenin is a phytochemical mixture found in many plant species, including the Inula helenium (elecampane) of the family Asteraceae. It is a mixture of two isomeric sesquiterpene lactones, alantolactone and isoalantolactone. Helenin can be extracted from the roots of Inula helenium using alcohol or other non-polar solvents to produce a mixture with a composition of about 40% alantolactone and 60% isoalantolactone. 8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one is found in Abutilon indicum, Artemisia feddei, Carpesium longifolium, Carpesium macrocephalum, Inula helenium, Inula magnifica, Inula racemosa, Inula salicina, Lophocolea heterophylla, Ratibida columnifera, Telekia speciosa, Tritomaria quinquedentata and Xanthium indicum. Alantolactone has a variety of in vitro biochemical properties, including:Induces apoptosis and cell cycle arrest in lung squamous cancer cellssuppresses STAT3 activationhas antiinflammatory effects by inhibiting chemokine production and STAT1 phosphorylationanti-fungalanti-microbialCertain individuals have experienced contact dermatitis when exposed to alantolactone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.6835    1.5502   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528    0.4320   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079   -0.6691    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6136   -0.8140    1.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4650   -1.6192    0.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958   -0.9110    0.5389 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2000   -1.7355   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287   -0.8665   -0.5746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0825   -1.2518   -2.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1843   -1.3530    0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7965   -0.4411    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8435    0.4953    1.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334    1.2950    0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1539    2.6136    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950    0.5867   -0.5387 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7099    1.0592   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -0.0201   -0.6333 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6306    1.7754    0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    2.3103   -0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -0.3079    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6896   -2.3452   -0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1223   -2.4637    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2712   -0.7776   -2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158   -2.3439   -2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0746   -0.8376   -2.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034   -1.6012   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324   -2.3397    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3286   -1.0055    1.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5862    0.1878    0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697    1.2103    2.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399    0.0473    2.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7005    3.1606   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5271    3.1642    1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2895    1.0578   -1.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227    1.8353    0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814    1.5593   -1.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8438   -0.6370   -1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
  6  7  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
 15  8  1  0
  2 17  1  0
  7  8  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  6
 16 35  1  0
 16 36  1  0
 17 37  1  6
  6 20  1  1
  7 21  1  0
  7 22  1  0
  1 18  1  0
  1 19  1  0
M  END


  Mrv0541 05061308482D          

 17 19  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  2  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3

> <INCHI_KEY>
CVUANYCQTOGILD-UHFFFAOYSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.3181

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.456967674758026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.357975322

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.864710029813113

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.1974

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.942   0.369   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.466   1.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.371   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.911   3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.466   4.326   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   15                                                       
CONECT    7   11   12                                                       
CONECT    8   13   15                                                       
CONECT    9    1    5   12                                                  
CONECT   10    2   11   14                                                  
CONECT   11    7   10   13                                                  
CONECT   12    7    9   15                                                  
CONECT   13    8   11   17                                                  
CONECT   14   10   16   17                                                  
CONECT   15    3    6    8   12                                             
CONECT   16   14                                                            
CONECT   17   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
Isohelenin	HMDB

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3181 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

Traditional Name

8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C

InChI Identifier

InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3

InChI Key

CVUANYCQTOGILD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abutilon indicum	LOTUS Database	35616633
Artemisia feddei	LOTUS Database	35616633
Carpesium longifolium	LOTUS Database	35616633
Carpesium macrocephalum	LOTUS Database	35616633
Inula helenium	LOTUS Database	35616633
Inula magnifica	LOTUS Database	35616633
Inula racemosa	LOTUS Database	35616633
Inula salicina	LOTUS Database	35616633
Lophocolea heterophylla	LOTUS Database	35616633
Ratibida columnaris	LOTUS Database	35616633
Telekia speciosa	LOTUS Database	35616633
Trilophozia quinquedentata	LOTUS Database	35616633
Xanthium indicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.15	ALOGPS
logP	3.36	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.2 m³·mol⁻¹	ChemAxon
Polarizability	26.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035934

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Helenin

METLIN ID

Not Available

PubChem Compound

605266

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one (NP0181082)

MOL for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

3D MOL for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

3D SDF for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

3D-SDF for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

PDB for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

3D PDB for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

SMILES for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

INCHI for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

Structure for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)

3D Structure for NP0181082 (8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one)