NP-MRD: Showing NP-Card for gamma-Caryophyllene (NP0045186)

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Record Information

Version

2.0

Created at

2022-03-10 18:59:26 UTC

Updated at

2022-03-10 22:20:49 UTC

NP-MRD ID

NP0045186

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Caryophyllene

Description

Iso-caryophyllene also called cis-beta-caryophyllene (E-BCP) is a cis-double-bond isomer of trans-beta-caryophyllene. Caryophyllene has three isomers, cis-beta-caryophyllene, trans-beta-caryophyllene and alpha-caryophyllene (also called alpha humulene). All three isomers are found together in plants. Iso-caryophyllene belongs to the class of organic compounds known as sesquiterpenoids. It is formally classified as a polycyclic hydrocarbon although it is biochemically a bicyclic sesquiterpenoid as it is synthesized via multiple isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Thus, isocaryophyllene is considered to be an isoprenoid lipid molecule. Iso-caryophyllene is a neutral, hydrophobic molecule, that is practically insoluble in water. It has a woody, spicy odor and can be used as a perfuming agent and a food additive (PMID: 27696789 ). Iso-caryophyllene is a naturally occurring sesquiterpenoid found in allspice, anise, basil, cinnamon, lime, black pepper, sage, spearmint, cloves, rosemary and hops and is widespread in plants (Jasminum, Origanum, and Pimpinella species). It is also one of more than 140 terpenoids that are found in cannabis plants (PMID:6991645 ) And the combination of these terpenoids produces the skunky, fruity odor characteristic of C. Savita. Iso-caryophyllene is also called a phytocannabinoid and is able to bind to the CB2 (cannabinoid) receptor (PMID: 27696789 ). Binding to CB2 results in the activation of Galphai/o protein, which leads to decline of cAMP production and in consequence inhibition of adenylyl cyclase. In addition, ligand‚Äö√Ñ√™coupled CB2 activate Ggammabeta proteins and stimulate both mitogen‚Äö√Ñ√™activated protein kinase (MAPK) and phosphoinositide 3‚Äö√Ñ√™kinase (PI3K) signaling pathways (PMID: 27696789 ). Iso-caryophyllene is thought to possess anti-cancer and anti-angiogenic activities through induction of apoptosis (2) repression of cell cycle, and (3) inhibition of angiogenesis and metastasis (PMID: 27696789 )

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    0.4601    3.3898   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1020    2.1838   -0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4457    2.0919    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1783    0.9350   -0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815   -0.0586    0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1352   -1.3174    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -2.2376    1.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4141   -1.8409   -0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0179   -1.4720   -0.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172   -0.2121   -0.0625 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5788    0.9540   -1.0091 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0583    1.0517   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416   -0.1814    0.1168 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6553   -1.3366   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039   -0.0217    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    3.5226   -1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    4.2809   -0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976    1.9476    1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0444    3.0235   -0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1769    1.2494   -0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6551    0.4692   -1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098    0.3117    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0206   -3.2399    1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843   -2.4261    1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2164   -1.7782    2.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9982   -1.5300   -1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695   -2.9699   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -1.3640   -1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6988   -2.2885   -0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420    0.0289    0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947    0.7051   -2.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7171    0.9534   -1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838    1.9424   -0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882   -1.5356   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6865   -2.2368    0.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7219   -0.9913   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6389    0.4630    2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354    0.5787    1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584   -1.0441    1.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 13 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 10 11  1  0
  2 11  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 10 30  1  1
  9 28  1  0
  9 29  1  0
  8 26  1  0
  8 27  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  5 22  1  0
  4 20  1  0
  4 21  1  0
  3 18  1  0
  3 19  1  0
  1 16  1  0
  1 17  1  0
M  END

  Mrv1652304022019462D          

 17 18  0  0  0  0            999 V2000
    0.9899   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0990   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2422    0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8297    0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545    1.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331    0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2509    1.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579   -1.2011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3579   -2.0261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4670   -2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670   -1.2011    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8135   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2147   -1.5498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870   -2.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1601   -2.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056   -1.5498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 12  1  0  0  0  0
  1  9  1  0  0  0  0
 12  2  1  0  0  0  0
  2 13  2  0  0  0  0
 10 15  1  6  0  0  0
 10 16  1  1  0  0  0
 12 14  1  1  0  0  0
  9 17  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0045186

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m1/s1

> <INCHI_KEY>
NPNUFJAVOOONJE-FLFDDASRSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.995274071404452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
4.519309391666669

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.45239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isocaryophyllene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0       1.848  -1.252   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.051  -1.252   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.319   0.264   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.549   1.598   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.102   2.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.345   1.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.115   0.264   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.335   2.778   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.668  -2.242   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.668  -3.782   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.872  -3.782   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.872  -2.242   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.385  -2.022   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      -2.267  -2.893   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       0.909  -5.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.166  -4.142   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       2.064  -2.893   0.000  0.00  0.00           H+0
CONECT    1    7    9                                                       
CONECT    2    3   12   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6                                                            
CONECT    9   10   12    1   17                                             
CONECT   10    9   11   15   16                                             
CONECT   11   10   12                                                       
CONECT   12   11    9    2   14                                             
CONECT   13    2                                                            
CONECT   14   12                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Gamma-Caryophyllene	HMDB
g-Caryophyllene	HMDB
Γ-caryophyllene	HMDB
Caryophyllene, (r,4Z,9S)-(+-)-isomer	HMDB
Caryophyllene	HMDB
Caryophyllene, (R-(r*,4E,9S))-isomer	HMDB
Caryophyllene, (R-(r,4Z,9S))-isomer	HMDB
Caryophyllene, (S-(r,4E,9S))-isomer	HMDB
Caryophyllene, (S-(r,4Z,9S))-isomer	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

Traditional Name

isocaryophyllene

CAS Registry Number

118-65-0

SMILES

[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C

InChI Identifier

InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m1/s1

InChI Key

NPNUFJAVOOONJE-FLFDDASRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acca sellowiana	LOTUS Database	35616633
Aloysia gratissima	LOTUS Database	35616633
Aloysia triphylla	LOTUS Database	35616633
Angelica archangelica	LOTUS Database	35616633
Aristolochia elegans	LOTUS Database	35616633
Artemisia filifolia	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Azadirachta indica	LOTUS Database	35616633
Baccharis coridifolia	LOTUS Database	35616633
Blepharocalyx tweediei	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Cassinia laevis	LOTUS Database	35616633
Citrus junos	LOTUS Database	35616633
Citrus wilsonii	LOTUS Database	35616633
Conyza bonariensis	LOTUS Database	35616633
Conyza sumatrensis	LOTUS Database	35616633
Croton flavens	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cuminum cyminum	LOTUS Database	35616633
Curcuma pierreana	LOTUS Database	35616633
Dendropanax trifidus	LOTUS Database	35616633
Eugenia uniflora	LOTUS Database	35616633
Heterotheca subaxillaris	LOTUS Database	35616633
Ocimum gratissimum	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Persicaria minor	LOTUS Database	35616633
Phyla dulcis	LOTUS Database	35616633
Piper nigrum	LOTUS Database	35616633
Salvia dorisiana	LOTUS Database	35616633
Santolina chamaecyparissus	LOTUS Database	35616633
Satureja cuneifolia	LOTUS Database	35616633
Tetradenia riparia	LOTUS Database	35616633
Vismia cayennensis	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

Caryophyllane sesquiterpenoid
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

sesquiterpenoid (CHEBI:5993 )
Caryophyllane sesquiterpenoids (C09691 )
Humulenes (C09691 )
Caryophyllane sesquiterpenoids (LMPR0103120002 )

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	5.35	ALOGPS
logP	4.52	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	0	ChemAxon
Refractivity	67.45 m³·mol⁻¹	ChemAxon
Polarizability	26 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

HMDB0061779

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00012474

Chemspider ID

Not Available

KEGG Compound ID

C09691

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281522

PDB ID

Not Available

ChEBI ID

5993

Good Scents ID

Not Available

References

General References

Fidyt K, Fiedorowicz A, Strzadala L, Szumny A: beta-caryophyllene and beta-caryophyllene oxide-natural compounds of anticancer and analgesic properties. Cancer Med. 2016 Oct;5(10):3007-3017. doi: 10.1002/cam4.816. Epub 2016 Sep 30. [PubMed:27696789 ]
Jelen HH, Mirocha CJ, Wasowicz E, Kaminski E: Production of volatile sesquiterpenes by Fusarium sambucinum strains with different abilities to synthesize trichothecenes. Appl Environ Microbiol. 1995 Nov;61(11):3815-20. doi: 10.1128/aem.61.11.3815-3820.1995. [PubMed:8526491 ]
Demirci B, Baser KH, Ozek T, Demirci F: Betulenols from Betula species. Planta Med. 2000 Jun;66(5):490-3. doi: 10.1055/s-2000-8591. [PubMed:10909279 ]
Hernandez T, Canales M, Avila JG, Garcia AM, Martinez A, Caballero J, de Vivar AR, Lira R: Composition and antibacterial activity of essential oil of Lantana achyranthifolia Desf. (Verbenaceae). J Ethnopharmacol. 2005 Jan 15;96(3):551-4. doi: 10.1016/j.jep.2004.09.044. [PubMed:15619577 ]
Ricci D, Fraternale D, Giamperi L, Bucchini A, Epifano F, Burini G, Curini M: Chemical composition, antimicrobial and antioxidant activity of the essential oil of Teucrium marum (Lamiaceae). J Ethnopharmacol. 2005 Apr 8;98(1-2):195-200. doi: 10.1016/j.jep.2005.01.022. [PubMed:15763383 ]
Sabulal B, Dan M, J AJ, Kurup R, Pradeep NS, Valsamma RK, George V: Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: Chemical characterization and antimicrobial activity. Phytochemistry. 2006 Nov;67(22):2469-73. doi: 10.1016/j.phytochem.2006.08.003. Epub 2006 Sep 14. [PubMed:16973189 ]
Legault J, Pichette A: Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel. J Pharm Pharmacol. 2007 Dec;59(12):1643-7. doi: 10.1211/jpp.59.12.0005. [PubMed:18053325 ]
Ashitani T, Borg-Karlson AK, Fujita K, Nagahama S: Reaction mechanism of direct episulfidation of caryophyllene and humulene. Nat Prod Res. 2008 Apr 15;22(6):495-8. doi: 10.1080/14786410701591903. [PubMed:18415856 ]
Sousa EO, Silva NF, Rodrigues FF, Campos AR, Lima SG, Costa JG: Chemical composition and resistance-modifying effect of the essential oil of Lantana camara Linn. Pharmacogn Mag. 2010 Apr;6(22):79-82. doi: 10.4103/0973-1296.62890. Epub 2010 May 5. [PubMed:20668570 ]

Showing NP-Card for gamma-Caryophyllene (NP0045186)

MOL for NP0045186 (gamma-Caryophyllene)

3D MOL for NP0045186 (gamma-Caryophyllene)

3D SDF for NP0045186 (gamma-Caryophyllene)

3D-SDF for NP0045186 (gamma-Caryophyllene)

PDB for NP0045186 (gamma-Caryophyllene)

3D PDB for NP0045186 (gamma-Caryophyllene)

SMILES for NP0045186 (gamma-Caryophyllene)

INCHI for NP0045186 (gamma-Caryophyllene)

Structure for NP0045186 (gamma-Caryophyllene)

3D Structure for NP0045186 (gamma-Caryophyllene)