NP-MRD: Showing NP-Card for 4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene (NP0254997)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 19:19:58 UTC

Updated at

2022-09-07 19:19:59 UTC

NP-MRD ID

NP0254997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene

Description

Beta-Selinene, also known as β-selinene or beta-eudesmene, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Thus, beta-selinene is considered to be an isoprenoid lipid molecule. Beta-Selinene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Beta-Selinene is a herbal tasting compound. Outside of the human body, beta-Selinene is found, on average, in the highest concentration within a few different foods, such as wild celeries, wild carrots, and carrots and in a lower concentration in parsley, lovages, and safflowers. Beta-Selinene has also been detected, but not quantified in, several different foods, such as alcoholic beverages, chinese cinnamons, roman camomiles, ceylon cinnamons, and sweet basils. This could make beta-selinene a potential biomarker for the consumption of these foods. 4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene is found in Abies magnifica, Abies sibirica, Alpinia intermedia, Asarum caulescens, Ayapana triplinervis, Callitris intratropica, Cedrela odorata, Coronidium glutinosum, Cyperus rotundus, Dacrydium cupressinum, Dendropanax trifidus, Eugenia uniflora, Fitchia speciosa, Gossypium hirsutum, Guarea guidonia, Humulus lupulus, Ichthyothere terminalis, Keteleeria davidiana, Laggera alata, Linzia glabra, Molopospermum peloponnesiacum, Neolitsea aciculata, Piper aduncum, Rudbeckia mollis, Senecio nebrodensis, Valeriana officinalis, Vismia cayennensis and Xanthium strumarium. A selinene that is decahydronaphthalene substituted by a isopropenyl group at position 7, a methyl group at position 4a and a methylidene group at position 1.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    2.2958    1.8526    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962    0.5627    0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141    0.1860    1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563   -0.5293   -0.3607 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3773   -1.4805    0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0014   -2.0114    0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590   -1.0176    0.1575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7985   -1.5283   -1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0813   -0.8374    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2031    0.5556    1.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3212    1.6172    0.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3701    1.3343   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909    1.9972   -1.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788    0.3012   -0.1380 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6881    0.0608   -1.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192    2.5953    0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4430    2.2347   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6956    0.2337    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730   -0.7927    1.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9591    0.9287    1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -1.0064   -1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0716   -2.3462    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4619   -0.9913    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0383   -2.8796   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054   -2.4617    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1508   -2.1474   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -2.2219   -0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3242   -0.7305   -1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -1.1966    0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7567   -1.4785    2.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799    0.7761    2.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    0.6060    2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458    2.5654    1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384    1.7934    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653    2.7538   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7967    1.7701   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021    0.6056    0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655   -0.6568   -1.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312    0.9836   -1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 12 14  1  0
 14 15  1  0
 15  4  1  0
 14  7  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  1 16  1  0
  1 17  1  0
  4 21  1  6
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  1
 15 38  1  0
 15 39  1  0
M  END


  Mrv0541 05061308102D          

 15 16  0  0  0  0            999 V2000
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
    2.8579    1.6500    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 11  1  2  0  0  0  0
 11  2  1  0  0  0  0
 12  3  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC2(C)CCCC(=C)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3

> <INCHI_KEY>
YOVSPTNQHMDJAG-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
26.02296702692417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-decahydronaphthalene

> <ALOGPS_LOGP>
5.26

> <JCHEM_LOGP>
4.577243062000001

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
66.37989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene

> <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      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   15                                                            
CONECT    5    6    8                                                       
CONECT    6    5   12                                                       
CONECT    7    9   13                                                       
CONECT    8    5   15                                                       
CONECT    9    7   15                                                       
CONECT   10   13   14                                                       
CONECT   11    1    2   13                                                  
CONECT   12    3    6   14                                                  
CONECT   13    7   10   11                                                  
CONECT   14   10   12   15                                                  
CONECT   15    4    8    9   14                                             
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
7-Isopropenyl-4a-methyl-1-methylenedecahydronaphthalene	ChEBI
b-Selinene	Generator
Β-selinene	Generator
(+)-beta-Selinene	HMDB
beta-Eudesmene	HMDB
Cyperene II	HMDB
Eudesma-4(14),11-diene	HMDB
Selina-4(10),11-diene	HMDB
Selina-4(14),11-diene	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-decahydronaphthalene

Traditional Name

4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene

CAS Registry Number

Not Available

SMILES

CC(=C)C1CCC2(C)CCCC(=C)C2C1

InChI Identifier

InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3

InChI Key

YOVSPTNQHMDJAG-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
Abies magnifica	LOTUS Database	35616633
Abies sibirica	LOTUS Database	35616633
Alpinia intermedia	LOTUS Database	35616633
Asarum caulescens	LOTUS Database	35616633
Ayapana triplinervis	LOTUS Database	35616633
Callitris intratropica	LOTUS Database	35616633
Cedrela odorata	LOTUS Database	35616633
Coronidium glutinosum	LOTUS Database	35616633
Cyperus rotundus	LOTUS Database	35616633
Dacrydium cupressinum	LOTUS Database	35616633
Dendropanax trifidus	LOTUS Database	35616633
Eugenia uniflora	LOTUS Database	35616633
Fitchia speciosa	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Guarea guidonia	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Ichthyothere terminalis	LOTUS Database	35616633
Keteleeria davidiana	LOTUS Database	35616633
Laggera alata	LOTUS Database	35616633
Linzia glabra	LOTUS Database	35616633
Molopospermum peloponnesiacum	LOTUS Database	35616633
Neolitsea aciculata	LOTUS Database	35616633
Piper aduncum	LOTUS Database	35616633
Rudbeckia mollis	LOTUS Database	35616633
Senecio nebrodensis	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633
Vismia cayennensis	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

selinene (CHEBI:49271 )
Eudesmane sesquiterpenoids (LMPR0103190009 )
a sesquiterpenoid (CPD-11504 )

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	5.26	ALOGPS
logP	4.58	ChemAxon
logS	-4.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.38 m³·mol⁻¹	ChemAxon
Polarizability	26.02 Å³	ChemAxon
Number of Rings	2	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

HMDB0034997

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

Not Available

METLIN ID

Not Available

PubChem Compound

519361

PDB ID

Not Available

ChEBI ID

49271

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene (NP0254997)

MOL for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

3D MOL for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

3D SDF for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

3D-SDF for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

PDB for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

3D PDB for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

SMILES for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

INCHI for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

Structure for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)

3D Structure for NP0254997 (4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene)