NP-MRD: Showing NP-Card for 1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene (NP0251465)

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Record Information

Version

2.0

Created at

2022-09-07 14:40:26 UTC

Updated at

2022-09-07 14:40:26 UTC

NP-MRD ID

NP0251465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene

Description

3,7(11)-Eudesmadiene, also known as selina-3,7(11)-dien or aristolochene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3,7(11)-Eudesmadiene is possibly neutral. Outside of the human body, 3,7(11)-Eudesmadiene is found, on average, in the highest concentration within gingers. 3,7(11)-Eudesmadiene has also been detected, but not quantified in, alcoholic beverages and fats and oils. 1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene is found in Abies firma, Asarum caulescens, Cymbopogon schoenanthus and Humulus lupulus. This could make 3,7(11)-eudesmadiene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.0265    2.9857   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6184    1.6444   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218    1.4908   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4813    0.0962   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6758   -0.7492    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239   -0.7575    0.2189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0665   -1.9841   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4254   -1.0687    1.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9546   -1.4422    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953   -0.2816    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169   -0.2250    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -1.2551    0.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4857    0.8854   -0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918    0.7724   -0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7686    0.4600   -0.5013 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2062    3.1550   -0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6142    3.1666    0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7542    3.8080   -0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6126    2.3167    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5457    0.0717   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -0.1884   -1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0589   -1.7784    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.2464    1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768   -2.9136   -0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581   -1.9664   -1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005   -1.9161   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3470   -0.1898    2.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219   -1.9366    1.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9968   -2.3679    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -1.6411    1.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6564   -1.3445    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737   -2.2108    0.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863   -0.9701    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4835    1.1048   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8508    1.7980   -0.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.6883   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806    1.0547   -1.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689    1.6913    0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9024    0.2438   -1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
 11 10  2  3
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  6
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 15  1  0
 15 14  1  0
 14 10  1  0
 15  6  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
  9 29  1  0
  9 30  1  0
  8 27  1  0
  8 28  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  5 22  1  0
  5 23  1  0
  4 20  1  0
  4 21  1  0
  3 19  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 15 39  1  6
 14 37  1  0
 14 38  1  0
M  END


  Mrv0541 05061309322D          

 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  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  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>
NP0251465

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,14H,5,7-10H2,1-4H3

> <INCHI_KEY>
WNRBYZQFEBIUGD-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
26.241188396587766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4a,8-dimethyl-2-(propan-2-ylidene)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

> <ALOGPS_LOGP>
5.78

> <JCHEM_LOGP>
4.417717896666666

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
68.25829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene

> <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
3,7(11)-Selinadiene	HMDB
Aristolochene	HMDB
Eudesma-3,7(11)-diene	HMDB
Selina-3,7(11)-dien	HMDB
Selina-3,7(11)-diene	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

4a,8-dimethyl-2-(propan-2-ylidene)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

Traditional Name

1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene

CAS Registry Number

Not Available

SMILES

CC(C)=C1CCC2(C)CCC=C(C)C2C1

InChI Identifier

InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,14H,5,7-10H2,1-4H3

InChI Key

WNRBYZQFEBIUGD-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 firma	LOTUS Database	35616633
Asarum caulescens	LOTUS Database	35616633
Cymbopogon schoenanthus	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

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

a sesquiterpenoid (CPD-8748 )

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	5.78	ALOGPS
logP	4.42	ChemAxon
logS	-3.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.26 m³·mol⁻¹	ChemAxon
Polarizability	26.24 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

HMDB0037060

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016043

KNApSAcK ID

C00012708

Chemspider ID

455601

KEGG Compound ID

Not Available

BioCyc ID

CPD-8748

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

522296

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene (NP0251465)

MOL for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

3D MOL for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

3D SDF for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

3D-SDF for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

PDB for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

3D PDB for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

SMILES for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

INCHI for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

Structure for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)

3D Structure for NP0251465 (1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene)