NP-MRD: Showing NP-Card for β-elemene (NP0320016)

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Record Information

Version

1.0

Created at

2022-09-11 21:21:37 UTC

Updated at

2022-09-11 21:21:37 UTC

NP-MRD ID

NP0320016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-elemene

Description

(-)-Beta-Elemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively (-)-beta-Elemene is possibly neutral. Outside of the human body, (-)-beta-Elemene has been detected, but not quantified in, herbs and spices and root vegetables. β-elemene is found in Acca sellowiana, Acorus gramineus, Artemisia carvifolia, Artemisia herba-alba, Asarum megacalyx, Callitris columellaris, Cinnamomum camphora, Citrus unshiu, Clavularia viridis, Commiphora kataf, Conocephalum conicum, Cyperus conglomeratus, Dacrydium cupressinum, Dictyopteris divaricata, Eugenia uniflora, Frullania tamarisci, Mesosphaerum suaveolens, Juniperus rigida, Linzia glabra, Machilus japonica, Machilus thunbergii, Mentha piperita, Mentha suaveolens, Micromeria croatica, Nelumbo lutea, Nigella damascena, Perezia carthamoides, Petasites albus, Piper aduncum, Riccardia multifida, Santolina chamaecyparissus, Saussurea costus, Scapania undulata, Sinularia flexibilis, Tagetes minuta, Thujopsis dolabrata, Thymus marschallianus, Tritomaria quinquedentata, Trixis inula, Valeriana officinalis and Xylopia aromatica. This could make (-)-beta-elemene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -2.9826   -0.7848    1.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4982   -0.0559    0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359   -0.5846   -0.1042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9575   -1.5886   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5222   -1.4080    0.8372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8168   -1.6805    0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5508   -0.3625    0.2425 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9953   -0.4638   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5251   -1.6041   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359    0.7399    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514    0.6105   -0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5947    0.4686   -0.8393 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2287    1.7932   -0.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9516    2.4914   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500    2.3598    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408   -0.4447    2.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5976   -1.7501    1.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9802    0.8931    0.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794   -2.5770   -0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573   -1.7318   -1.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815   -1.2005   -1.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9641   -2.4373    0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3739   -0.9710    1.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4043   -2.4176    0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076   -1.9620   -0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3979    0.0373    1.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -2.5307   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6005   -1.6337   -0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7236    0.6155   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2762    0.7187    1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    1.6803   -0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1595    1.6345   -0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4089    0.5391   -1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105    0.3450   -1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1452    2.1736   -2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    3.4308   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9743    1.5973    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657    2.9686    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142    3.0917    0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  1  0
  8  9  2  3
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  1
  2  1  2  3
  3 12  1  0
 12 11  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  3
 11  7  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
  9 27  1  0
  9 28  1  0
  7 26  1  1
  6 24  1  0
  6 25  1  0
  5 22  1  0
  5 23  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  2 18  1  0
  1 16  1  0
  1 17  1  0
 12 34  1  6
 11 32  1  0
 11 33  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 14 35  1  0
 14 36  1  0
M  END


  Mrv0541 02241218072D          

 15 15  0  0  0  0            999 V2000
   -0.7130    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005    1.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279   -1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130    1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0320016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC(C)(C=C)C(C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3

> <INCHI_KEY>
OPFTUNCRGUEPRZ-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
26.046312286940775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
4.736980978333334

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
68.22619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-β-elemene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.331   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.331  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.001  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.331  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.331   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.001   1.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.665   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.000   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.000  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.665  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.665  -2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.331   2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.666  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.000  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.666  -2.695   0.000  0.00  0.00           C+0
CONECT    1    2    6    7   12                                             
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    2    9   11                                                  
CONECT   11   10                                                            
CONECT   12    1                                                            
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(-)-b-Elemene	Generator
(-)-Β-elemene	Generator
Elemene	MetaCyc
2,4-Diisopropenyl-1-methyl-1-vinylcyclohexane	MetaCyc
1-Ethenyl-1-methyl-2,4-bis(1-methylethenyl)-cyclohexane	MetaCyc
levo-beta-Elemene	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane

Traditional Name

(-)-β-elemene

CAS Registry Number

Not Available

SMILES

CC(=C)C1CCC(C)(C=C)C(C1)C(C)=C

InChI Identifier

InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3

InChI Key

OPFTUNCRGUEPRZ-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
Acca sellowiana	LOTUS Database	35616633
Acorus gramineus	LOTUS Database	35616633
Artemisia carvifolia	LOTUS Database	35616633
Artemisia herba-alba	LOTUS Database	35616633
Asarum megacalyx	LOTUS Database	35616633
Callitris columellaris	LOTUS Database	35616633
Cinnamomum camphora	LOTUS Database	35616633
Citrus unshiu	LOTUS Database	35616633
Clavularia viridis	LOTUS Database	35616633
Commiphora kataf	LOTUS Database	35616633
Conocephalum conicum	LOTUS Database	35616633
Cyperus conglomeratus	LOTUS Database	35616633
Dacrydium cupressinum	LOTUS Database	35616633
Dictyopteris divaricata	LOTUS Database	35616633
Eugenia uniflora	LOTUS Database	35616633
Frullania tamarisci	LOTUS Database	35616633
Hyptis suaveolens	LOTUS Database	35616633
Juniperus rigida	LOTUS Database	35616633
Linzia glabra	LOTUS Database	35616633
Machilus japonica	LOTUS Database	35616633
Machilus thunbergii	LOTUS Database	35616633
Mentha piperita	LOTUS Database	35616633
Mentha rotundifolia	LOTUS Database	35616633
Micromeria croatica	LOTUS Database	35616633
Nelumbo lutea	LOTUS Database	35616633
Nigella damascena	LOTUS Database	35616633
Perezia carthamoides	LOTUS Database	35616633
Petasites albus	LOTUS Database	35616633
Piper aduncum	LOTUS Database	35616633
Riccardia multifida	LOTUS Database	35616633
Santolina chamaecyparissus	LOTUS Database	35616633
Saussurea costus	LOTUS Database	35616633
Scapania undulata	LOTUS Database	35616633
Sinularia flexibilis	LOTUS Database	35616633
Tagetes minuta	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633
Thymus marschallianus	LOTUS Database	35616633
Trilophozia quinquedentata	LOTUS Database	35616633
Trixis inula	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633
Xylopia aromatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Elemane sesquiterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

a sesquiterpenoid (CPD-8232 )

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	5.4	ALOGPS
logP	4.74	ChemAxon
logS	-4.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.23 m³·mol⁻¹	ChemAxon
Polarizability	26.05 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

HMDB0035816

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014578

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

10583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for β-elemene (NP0320016)

MOL for NP0320016 (β-elemene)

3D MOL for NP0320016 (β-elemene)

3D SDF for NP0320016 (β-elemene)

3D-SDF for NP0320016 (β-elemene)

PDB for NP0320016 (β-elemene)

3D PDB for NP0320016 (β-elemene)

SMILES for NP0320016 (β-elemene)

INCHI for NP0320016 (β-elemene)

Structure for NP0320016 (β-elemene)

3D Structure for NP0320016 (β-elemene)