NP-MRD: Showing NP-Card for 4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene (NP0163712)

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Record Information

Version

2.0

Created at

2022-09-02 22:25:49 UTC

Updated at

2022-09-02 22:25:49 UTC

NP-MRD ID

NP0163712

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene

Description

Beta-Cadinene, also known as β-cadinene or cadina-3,9-diene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Beta-Cadinene is possibly neutral. Beta-Cadinene is a green and woody tasting compound. Outside of the human body, beta-Cadinene has been detected, but not quantified in, several different foods, such as common oregano, common thymes, gingers, and sweet basils. 4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene is found in Acorus gramineus, Baccharis genistelloides, Larix gmelinii, Solidago canadensis and Valeriana officinalis. This could make beta-cadinene 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
    2.3998   -2.9034   -0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -1.5279   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493   -0.5330   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012    0.8914   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651    1.1011    0.1277 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3939    2.4086   -0.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561    3.4617   -0.7256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8788    2.6520    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896    1.5204    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3748    0.3125   -0.1957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3850   -0.7409    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3450   -1.1690    1.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3646   -1.9136   -0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0290   -0.0518   -0.2732 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5278   -1.2023    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0577   -3.0333   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6051   -0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -3.1437    0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459   -0.7798   -0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844    1.4794    0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2682    1.2601   -1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996    1.0291    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3205    3.1930   -0.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913    4.4151   -0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9789    3.7175   -1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867    3.6158   -0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4069    1.3214    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7485    1.7627    0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056    0.6832   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3801   -0.2591    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401   -0.6921    2.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231   -1.0449    2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1235   -2.2756    1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -2.8434   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -1.8739   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2642   -1.9632   -1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221   -0.2565   -1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379   -2.1232    0.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7661   -0.8891    1.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  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
 14  5  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 11 30  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 10 29  1  6
  9 27  1  0
  9 28  1  0
  8 26  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  5 22  1  1
  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 38  1  0
 15 39  1  0
 14 37  1  6
M  END


  Mrv1652307201900082D          

 15 16  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -0.4125    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
    1.4289    0.8250    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
    2.8579    0.0000    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163712

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CC=C(C)C2CC=C(C)CC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-6,10,13-15H,7-9H2,1-4H3

> <INCHI_KEY>
USDOQCCMRDNVAH-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.269889222572793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,8,8a-hexahydronaphthalene

> <ALOGPS_LOGP>
5.29

> <JCHEM_LOGP>
4.448347697666667

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.5984

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   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       2.667  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    4    9                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
b-Cadinene	Generator
Β-cadinene	Generator
(-)-beta-Cadinene	HMDB
Cadina-3,9-diene	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,8,8a-hexahydronaphthalene

Traditional Name

4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene

CAS Registry Number

Not Available

SMILES

CC(C)C1CC=C(C)C2CC=C(C)CC12

InChI Identifier

InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-6,10,13-15H,7-9H2,1-4H3

InChI Key

USDOQCCMRDNVAH-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
Acorus gramineus	LOTUS Database	35616633
Baccharis genistelloides	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Valeriana officinalis	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
Cadinane 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-8796 )

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	5.29	ALOGPS
logP	4.45	ChemAxon
logS	-4.3	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	68.6 m³·mol⁻¹	ChemAxon
Polarizability	26.27 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

HMDB0041576

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

521380

PDB ID

Not Available

ChEBI ID

27723

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene (NP0163712)

MOL for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

3D MOL for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

3D SDF for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

3D-SDF for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

PDB for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

3D PDB for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

SMILES for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

INCHI for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

Structure for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)

3D Structure for NP0163712 (4-isopropyl-1,6-dimethyl-3,4,4a,5,8,8a-hexahydronaphthalene)