NP-MRD: Showing NP-Card for Gamma-Curcumene (NP0045061)

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Record Information

Version

2.0

Created at

2022-03-10 18:57:19 UTC

Updated at

2022-03-10 22:20:50 UTC

NP-MRD ID

NP0045061

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gamma-Curcumene

Description

Gamma-Curcumene, also known as curcumene, belongs to the class of organic compounds known as sesquiterpenoids. These 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-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ) 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. Gamma-Curcumene is one of the terpenes found in Cannabis sativa (PMID: 6991645 ). It has also been identified in the essential oil of Lantana camara (west Indian lantana) (7.5% Relative to total oil composition) (PMID: 20645797 ), Valeriana wallichii (Indian Valerian) (10.7% Relative to total volatile composition) and helichrysum essential oil (13.9% Relative to total oil components) (DOI: 10.1016/J.Biopen.2017.04.001).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    5.4154    0.5378   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066    0.3269   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    1.5495   -0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776   -0.8787   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1657   -1.5151   -0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9887   -0.6342   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3207   -1.3845    0.1428 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3811   -2.1384    1.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952   -0.4628   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2956    0.8135   -0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144    1.7245   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6426    1.2929   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8045    2.2499   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9629   -0.1027   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475   -1.0425    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8365    0.9642    0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9206   -0.4225   -0.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6161    1.2128   -1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2822    1.5739   -0.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    1.6501    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7607    2.4787   -0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3154   -1.6712   -0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1290   -2.2997   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602   -2.0504    0.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0030    0.1579    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9287   -0.1801   -1.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -2.1098   -0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622   -1.4913    2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949   -2.9339    1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3397   -2.6773    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861    1.2517   -0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714    2.7878   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5318    3.1213   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6444    1.6954   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0920    2.5957    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6571   -0.1607    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6360   -0.5063   -0.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8795   -1.4050    1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -1.9178   -0.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15  9  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  7 27  1  6
  6 25  1  0
  6 26  1  0
  5 23  1  0
  5 24  1  0
  4 22  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652303192001383D          

 15 15  0  0  0  0            999 V2000
   -5.1873    0.7492    0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2456   -1.5550    1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    0.1514    0.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5810    1.5727   -0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035   -1.1695   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676   -0.1792   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6400   -0.8533   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3619   -0.6021    0.8625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8601    1.1804   -0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281   -0.6084    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4099    1.2496   -0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518   -0.3234    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297    0.2060    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781    0.2566   -0.7260 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5235    0.2843   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
 14  4  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 12  2  3  0  0  0
  7 14  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  2  0  0  0  0
  9 11  1  0  0  0  0
  9 13  1  0  0  0  0
 10 15  2  0  0  0  0
 11 15  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045061

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC=C(C)C)C1=CC=C(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14H,5,7,9,11H2,1-4H3/t14-/m1/s1

> <INCHI_KEY>
NGIVKZGKEPRIGG-CQSZACIVSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.407833193366674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene

> <ALOGPS_LOGP>
6.07

> <JCHEM_LOGP>
4.821593256333333

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
71.3554

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-curcumene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -5.187   0.749   0.392  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.246  -1.555   1.152  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.696   0.151   0.698  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.581   1.573  -0.560  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.003  -1.169  -0.542  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.068  -0.179  -0.438  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.640  -0.853  -0.078  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.362  -0.602   0.863  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.860   1.180  -0.697  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.928  -0.608   0.555  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.410   1.250  -0.991  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.152  -0.323   0.355  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.230   0.206   0.322  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.078   0.257  -0.726  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.524   0.284  -0.332  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    6    7                                                       
CONECT    6    5   12                                                       
CONECT    7    5   14                                                       
CONECT    8   10   13                                                       
CONECT    9   11   13                                                       
CONECT   10    8   15                                                       
CONECT   11    9   15                                                       
CONECT   12    1    2    6                                                  
CONECT   13    3    8    9                                                  
CONECT   14    4    7   15                                                  
CONECT   15   10   11   14                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
g-Curcumene	Generator
Γ-curcumene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene

Traditional Name

gamma-curcumene

CAS Registry Number

Not Available

SMILES

C[C@H](CCC=C(C)C)C1=CC=C(C)CC1

InChI Identifier

InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14H,5,7,9,11H2,1-4H3/t14-/m1/s1

InChI Key

NGIVKZGKEPRIGG-CQSZACIVSA-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
Ageratina adenophora	Plant	KNApSAcK
Anthemis aciphylla	LOTUS Database	35616633
Anthemis aciphylla BOISS.var.discoidea BOISS	Plant	KNApSAcK
Artemisia frigida	LOTUS Database	35616633
Artemisia schmidtiana	LOTUS Database	35616633
Asteriscus sericeus	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Callitropsis nootkatensis	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Cotula cinerea	LOTUS Database	35616633
Curcuma longa	Plant	KNApSAcK
Encelia canescens	LOTUS Database	35616633
Guatteriopsis blepharophylla	Plant	KNApSAcK
Helichrysum italicum	Plant	KNApSAcK
Helichrysum stenopterum	LOTUS Database	35616633
Hypericum androsaemum	LOTUS Database	35616633
Juglans regia	LOTUS Database	35616633
Murraya paniculata	Plant	KNApSAcK
Olearia teretifolia	LOTUS Database	35616633
Osyris quadripartita	LOTUS Database	35616633
Osyris tenuifolia	Plant	KNApSAcK
Plazia daphnoides	LOTUS Database	35616633
Salvia africana-lutea	LOTUS Database	35616633
Santolina corsica Jordan et Fourr	Plant	KNApSAcK
Sideritis montana	LOTUS Database	35616633
Tanacetum macrophyllum	Plant	KNApSAcK
Ursinia nana	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

Bisabolane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

alicyclic compound (CHEBI:63696 )
sesquiterpene (CHEBI:63696 )

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	6.07	ALOGPS
logP	4.82	ChemAxon
logS	-4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.36 m³·mol⁻¹	ChemAxon
Polarizability	26.41 Å³	ChemAxon
Number of Rings	1	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

C00030346

Chemspider ID

Not Available

KEGG Compound ID

C20179

BioCyc ID

CPD-11393

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304273

PDB ID

Not Available

ChEBI ID

63696

Good Scents ID

Not Available

References

General References

Kurade NP, Jaitak V, Kaul VK, Sharma OP: Chemical composition and antibacterial activity of essential oils of Lantana camara, Ageratum houstonianum and Eupatorium adenophorum. Pharm Biol. 2010 May;48(5):539-44. doi: 10.3109/13880200903193336. [PubMed:20645797 ]
Deguerry F, Pastore L, Wu S, Clark A, Chappell J, Schalk M: The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases. Arch Biochem Biophys. 2006 Oct 15;454(2):123-36. doi: 10.1016/j.abb.2006.08.006. Epub 2006 Aug 23. [PubMed:16970904 ]

Showing NP-Card for Gamma-Curcumene (NP0045061)

MOL for NP0045061 (Gamma-Curcumene)

3D MOL for NP0045061 (Gamma-Curcumene)

3D SDF for NP0045061 (Gamma-Curcumene)

3D-SDF for NP0045061 (Gamma-Curcumene)

PDB for NP0045061 (Gamma-Curcumene)

3D PDB for NP0045061 (Gamma-Curcumene)

SMILES for NP0045061 (Gamma-Curcumene)

INCHI for NP0045061 (Gamma-Curcumene)

Structure for NP0045061 (Gamma-Curcumene)

3D Structure for NP0045061 (Gamma-Curcumene)