NP-MRD: Showing NP-Card for 3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one (NP0209806)

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Record Information

Version

2.0

Created at

2022-09-05 07:21:58 UTC

Updated at

2022-09-05 07:21:59 UTC

NP-MRD ID

NP0209806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one

Description

Dihydroisoalantolactone, also known as 4(15)-eudesmen-12,8b-olide, 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. Dihydroisoalantolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dihydroisoalantolactone has been detected, but not quantified in, herbs and spices. 3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one is found in Artemisia lancea, Callitris columellaris, Carpesium longifolium, Carpesium macrocephalum, Inula helenium and Inula racemosa. This could make dihydroisoalantolactone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.6756    1.6290    2.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    0.6724    1.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115    0.7546    1.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    0.8075   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6385   -0.4601   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817   -0.7108   -0.5956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8793   -2.1486   -0.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339    0.1640   -1.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -0.1368   -1.4698 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8796    0.6738   -2.2207 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1058    0.6681   -1.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537    1.1655   -2.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9121   -0.0291   -0.2754 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7867    0.4539    0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352    0.2893   -0.0552 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7715   -0.5520    0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7085   -0.4952    0.8248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2532    2.4601    2.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949    1.6799    2.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894    1.6116    1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2034   -0.2019    1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6099    1.6915   -0.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2223    0.8606   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1856   -1.3055   -0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -0.5007   -1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088   -2.2448   -1.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897   -2.6222   -0.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8157   -2.7721   -1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6136    1.2344   -1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8300   -0.0934   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -1.1750   -1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9552   -1.1419   -0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4368   -0.4092    1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737    0.7035    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4447    1.2848    0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3654    1.3678    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0379   -0.1899    1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1691   -1.5910    0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1099   -1.3921    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 15  1  0
  6 17  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 13 32  1  6
 15 36  1  1
 16 37  1  0
 16 38  1  0
 17 39  1  1
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  1
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  1  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>
NP0209806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CC3C(=C)CCCC3(C)CC2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h10-13H,1,4-8H2,2-3H3

> <INCHI_KEY>
YYJRTJYCOMIDIC-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.160130452874032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
3.2163206176666668

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.082164813493459

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.394

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8a-dimethyl-5-methylidene-octahydro-3H-naphtho[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
4(15)-Eudesmen-12,8b-olide	HMDB

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3340 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

3,8a-dimethyl-5-methylidene-dodecahydronaphtho[2,3-b]furan-2-one

Traditional Name

3,8a-dimethyl-5-methylidene-octahydro-3H-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1C2CC3C(=C)CCCC3(C)CC2OC1=O

InChI Identifier

InChI=1S/C15H22O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h10-13H,1,4-8H2,2-3H3

InChI Key

YYJRTJYCOMIDIC-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
Artemisia lancea	LOTUS Database	35616633
Callitris columellaris	LOTUS Database	35616633
Carpesium longifolium	LOTUS Database	35616633
Carpesium macrocephalum	LOTUS Database	35616633
Inula helenium	LOTUS Database	35616633
Inula racemosa	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
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	3.45	ALOGPS
logP	3.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-7.1	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	66.39 m³·mol⁻¹	ChemAxon
Polarizability	27.16 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

HMDB0035935

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014738

KNApSAcK ID

Not Available

Chemspider ID

4280210

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5104810

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one (NP0209806)

MOL for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

3D MOL for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

3D SDF for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

3D-SDF for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

PDB for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

3D PDB for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

SMILES for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

INCHI for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

Structure for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)

3D Structure for NP0209806 (3,8a-dimethyl-5-methylidene-octahydro-3h-naphtho[2,3-b]furan-2-one)