NP-MRD: Showing NP-Card for Œ≥-Cadinene (NP0137081)

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Record Information

Version

1.0

Created at

2022-05-30 16:41:07 UTC

Updated at

2022-05-30 16:41:07 UTC

NP-MRD ID

NP0137081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Œ≥-Cadinene

Description

(-)-Gamma-cadinene, also known as g-cadinene, belongs to the class of organic compounds known as sesquiterpenoids. Œ≥-Cadinene is found in Cedrela odorata, Conyza bonariensis, Cupressus sempervirens, Dendropanax trifidus, Juglans regia, Laurencia dendroidea, Piper aduncum, Shorea robusta, Teucrium polium, Teucrium scorodonia and Chrysopogon zizanioides. It was first documented in 2004 (PMID: 15516500). These are terpenes with three consecutive isoprene units (-)-gamma-cadinene is possibly neutral (PMID: 22164798).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    0.6495    2.9759    1.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438    2.1942    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4127    2.2333    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6651    1.1628   -0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909   -0.1923   -0.1082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1396   -0.9187    0.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5464   -0.9471    0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7001   -2.3490    1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1978   -0.1603    0.4243 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0878   -1.2342   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3391   -1.0407   -0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1871   -2.1969   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0085    0.2790   -0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2832    1.2118    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8236    1.1929    0.0825 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7022    2.9713    1.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0448    3.7076    2.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7517    3.1960    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845    1.9780    1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554    1.2042   -0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1307    1.4877   -1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612   -0.8319   -1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1589   -0.3913    1.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0805   -1.7849    0.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972   -1.1835   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146   -0.0296    0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5885   -2.8772    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8352   -2.4418    1.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5271   -2.9167    1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478   -0.1651    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7085   -2.2418   -0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564   -2.0015   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -3.1599   -0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1740   -2.1529   -0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235    0.7071   -1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0662    0.2351   -0.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343    0.8968    1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6333    2.2562    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8178    1.3271   -1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
 10  9  1  0
  9  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  5  6  1  0
  6  7  1  0
  6  8  1  0
  9 15  1  0
  2 15  1  0
 15 39  1  6
 14 37  1  0
 14 38  1  0
 13 35  1  0
 13 36  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 10 31  1  0
  9 30  1  1
  5 22  1  6
  4 20  1  0
  4 21  1  0
  3 18  1  0
  3 19  1  0
  1 16  1  0
  1 17  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
M  END


  Mrv1652309272007312D          

 17 18  0  0  0  0            999 V2000
 9998.914110001.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.198710001.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.629510001.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9141 9998.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.771210000.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6275 9998.5263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627510001.0119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.914110000.5944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.199610000.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1996 9999.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9141 9998.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.341310000.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.626810000.1819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6268 9999.3568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3413 9998.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0558 9999.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055810000.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8  1  1  6  0  0  0
 11  4  2  0  0  0  0
 17  5  1  0  0  0  0
 11 14  1  0  0  0  0
 14  6  1  1  0  0  0
  8 13  1  0  0  0  0
 13  7  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0137081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCC(C)=C[C@]1([H])[C@H](CCC2=C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m1/s1

> <INCHI_KEY>
WRHGORWNJGOVQY-RBSFLKMASA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.38047424511312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aS,8aS)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

> <ALOGPS_LOGP>
4.48

> <JCHEM_LOGP>
4.506281368000001

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.52590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-cadinene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8664.6408669.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3048670.101   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.9758670.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.6408663.139   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.9738667.785   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0    8665.9718663.916   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8665.9718668.556   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8664.6408667.776   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.3068667.006   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3068665.466   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6408664.696   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.3048667.776   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9708667.006   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.9708665.466   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.3048664.696   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.6378665.466   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.6378667.006   0.000  0.00  0.00           C+0
CONECT    1    2    3    8                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   11                                                            
CONECT    5   17                                                            
CONECT    6   14                                                            
CONECT    7   13                                                            
CONECT    8    9    1   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    4   14                                                  
CONECT   12   13   17                                                       
CONECT   13   12   14    8    7                                             
CONECT   14   13   15   11    6                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16    5                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
gamma-Cadinene	ChEBI
g-Cadinene	Generator
Γ-cadinene	Generator
(-)-g-Cadinene	Generator
(-)-Γ-cadinene	Generator
gamma-Cadinene, (+)-gamma(1)-isomer	MeSH
gamma-Cadinene, (-)-isomer	MeSH
gamma-Cadinene, (+)-isomer	MeSH
1beta,6alpha,7betaH-Cadina-4,10(15)-diene	PhytoBank
1β,6α,7βH-Cadina-4,10(15)-diene	PhytoBank
1beta,6alpha,7βH-Cadina-4,10(15)-diene	PhytoBank
(-)-gamma-Cadinene	PhytoBank
(±)-Cadina-4,10(15)-diene	PhytoBank
(±)-gamma-Cadinene	PhytoBank
(±)-γ-Cadinene	PhytoBank
gamma-Cardinene	PhytoBank
γ-Cardinene	PhytoBank

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1R,4aS,8aS)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

Traditional Name

gamma-cadinene

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC(C)=C[C@]1([H])[C@H](CCC2=C)C(C)C

InChI Identifier

InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m1/s1

InChI Key

WRHGORWNJGOVQY-RBSFLKMASA-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
Cedrela odorata	LOTUS Database	35616633
Conyza bonariensis	LOTUS Database	35616633
Cupressus sempervirens	LOTUS Database	35616633
Dendropanax trifidus	LOTUS Database	35616633
Juglans regia	LOTUS Database	35616633
Laurencia dendroidea	LOTUS Database	35616633
Piper aduncum	LOTUS Database	35616633
Shorea robusta	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Teucrium scorodonia	LOTUS Database	35616633
Vetiveria zizanioides	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

cadinene (CHEBI:63203 )

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	4.48	ALOGPS
logP	4.51	ChemAxon
logS	-4.5	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	67.53 m³·mol⁻¹	ChemAxon
Polarizability	26.38 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00030345 C00036278

Chemspider ID

Not Available

KEGG Compound ID

C19738

BioCyc ID

CPD-12881

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92313

PDB ID

Not Available

ChEBI ID

63203

Good Scents ID

Not Available

References

General References

Iijima Y, Davidovich-Rikanati R, Fridman E, Gang DR, Bar E, Lewinsohn E, Pichersky E: The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil. Plant Physiol. 2004 Nov;136(3):3724-36. doi: 10.1104/pp.104.051318. Epub 2004 Oct 29. [PubMed:15516500 ]
Arjouni MY, Bahri F, Romane A, El Fels MA: Chemical composition and antimicrobial activity of essential oil of Cupressus atlantica. Nat Prod Commun. 2011 Oct;6(10):1519-22. [PubMed:22164798 ]

Showing NP-Card for Œ≥-Cadinene (NP0137081)

MOL for NP0137081 (Œ≥-Cadinene)

3D MOL for NP0137081 (Œ≥-Cadinene)

3D SDF for NP0137081 (Œ≥-Cadinene)

3D-SDF for NP0137081 (Œ≥-Cadinene)

PDB for NP0137081 (Œ≥-Cadinene)

3D PDB for NP0137081 (Œ≥-Cadinene)

SMILES for NP0137081 (Œ≥-Cadinene)

INCHI for NP0137081 (Œ≥-Cadinene)

Structure for NP0137081 (Œ≥-Cadinene)

3D Structure for NP0137081 (Œ≥-Cadinene)