NP-MRD: Showing NP-Card for alpha-Curcumene (NP0044883)

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Record Information

Version

2.0

Created at

2022-03-10 18:45:44 UTC

Updated at

2022-03-10 22:18:03 UTC

NP-MRD ID

NP0044883

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Curcumene

Description

Alpha-Curcumene, or 2-methyl-6-p-tolyl-2-heptene, also known as ar-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; PMID:17467679 ), In the cytoplasm. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261 ). 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. Alpha-curcumene is possibly neutral. It has an herbal ordor. Alpha-curcumene has been detected in anise and carrot seeds, ginger and turmeric rhizomes and rhizome oils, and black pepper fruit and seeds and oils ( http://Www.Thegoodscentscompany.Com/data/rw1053941.Html#touses). It is also a component of Cannabis sativa (PMID: 6991645 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.2312   -0.8161   -1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0799    0.5268   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1267    1.5428   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579    0.8198    0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9903   -0.1564    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253    0.3119    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562   -0.7936    0.4521 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3404   -1.0303    1.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407   -0.4408    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -1.2842   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191   -0.9518   -1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3367    0.1792   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296    0.4846   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6221    1.0060    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396    0.7211    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1378   -1.6236   -0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1937   -0.9309   -1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662   -0.9154   -1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505    2.3441   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1413    1.0836   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9241    1.9517   -1.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954    1.8071    0.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2098   -1.0823   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -0.3344    1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255    1.2743    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6313    0.3182   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0773   -1.7342   -0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750   -0.0844    2.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2545   -1.6339    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5183   -1.6015    2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158   -2.1941   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2691   -1.6086   -1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8827    1.5762   -1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9507   -0.0681   -2.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3959    0.0716   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823    1.9054    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    1.3604    1.2303 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  2  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
 15 37  1  0
M  END

40681-06-9.mol
  Mrv1652303202019022D          

 15 15  0  0  0  0            999 V2000
   -2.5006   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -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  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  4  8  1  0  0  0  0
  1 15  1  0  0  0  0
  8  7  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044883

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m0/s1

> <INCHI_KEY>
VMYXUZSZMNBRCN-AWEZNQCLSA-N

> <FORMULA>
C15H22

> <MOLECULAR_WEIGHT>
202.341

> <EXACT_MASS>
202.172150708

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.114838897608152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-4-[(2S)-6-methylhept-5-en-2-yl]benzene

> <ALOGPS_LOGP>
6.15

> <JCHEM_LOGP>
5.391390631

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
69.0926

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.91e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-curcumene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 40681-06-9.mol                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -4.668  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.668   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.667   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.334   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.668   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.002  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    8                                                            
CONECT    8    9    4    7                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂

Average Mass

202.3410 Da

Monoisotopic Mass

202.17215 Da

IUPAC Name

1-methyl-4-[(2S)-6-methylhept-5-en-2-yl]benzene

Traditional Name

α-curcumene

CAS Registry Number

4176-06-1

SMILES

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

InChI Identifier

InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m0/s1

InChI Key

VMYXUZSZMNBRCN-AWEZNQCLSA-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
Antillogorgia rigida	LOTUS Database	35616633
Apium graveolens var. dulce	FooDB	Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Baeckea frutescens	-	KNApSAcK
Cannabis sativa	NULL	Not Available
Carica papaya L.	Plant	KNApSAcK
Chrysothamnus viscidiflorus	LOTUS Database	35616633
Citrus aurantiifolia	Plant	KNApSAcK
Citrus aurantium	Plant	KNApSAcK
Citrus limon	Plant	KNApSAcK
Citrus maxima	Plant	KNApSAcK
Citrus paradisi	Plant	KNApSAcK
Citrus reticulata	Plant	KNApSAcK
Curcuma amanda Roxb	Plant	KNApSAcK
Curcuma aromatica	Plant	KNApSAcK
Curcuma longa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dumortiera hirsuta	LOTUS Database	35616633
Endiandra xanthocarpa	LOTUS Database	35616633
Helichrysum italicum	Plant	KNApSAcK
Levisticum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Murraya paniculata	Plant	KNApSAcK
Persicaria minor	LOTUS Database	35616633
Picea koraiensis	LOTUS Database	35616633
Pimenta dioica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pinus sibirica	Plant	KNApSAcK
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Polygonum minus	Plant	KNApSAcK
Pseudopterogorgia rigida	-	KNApSAcK
Rhododendron dauricum	LOTUS Database	35616633
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber montanum	Plant	KNApSAcK
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
P-cymene
Toluene
Benzenoid
Monocyclic benzene moiety
Aromatic hydrocarbon
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Bisabolane sesquiterpenoids (LMPR0103060015 )

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	6.15	ALOGPS
logP	5.39	ChemAxon
logS	-5.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.09 m³·mol⁻¹	ChemAxon
Polarizability	26.11 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

FDB001523

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3083834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for alpha-Curcumene (NP0044883)

MOL for NP0044883 (alpha-Curcumene)

3D MOL for NP0044883 (alpha-Curcumene)

3D SDF for NP0044883 (alpha-Curcumene)

3D-SDF for NP0044883 (alpha-Curcumene)

PDB for NP0044883 (alpha-Curcumene)

3D PDB for NP0044883 (alpha-Curcumene)

SMILES for NP0044883 (alpha-Curcumene)

INCHI for NP0044883 (alpha-Curcumene)

Structure for NP0044883 (alpha-Curcumene)

3D Structure for NP0044883 (alpha-Curcumene)