NP-MRD: Showing NP-Card for β-bisabolene (NP0286921)

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Record Information

Version

1.0

Created at

2022-09-09 15:44:01 UTC

Updated at

2022-09-09 15:44:01 UTC

NP-MRD ID

NP0286921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-bisabolene

Description

Beta-Bisabolene, also known as β-bisabolen or b-limene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Beta-Bisabolene is possibly neutral. Outside of the human body, beta-Bisabolene has been detected, but not quantified in, carrots. β-bisabolene is found in Abies alba, Abies sibirica, Ambrosia trifida, Avena fatua, Callitropsis nootkatensis, Cochlospermum tinctorium, Copaifera paupera, Helianthus tuberosus, Helichrysum argyrophyllum, Petasites albus, Petasites japonicus, Pimpinella anisum, Pinus pumila, Rattus rattus, Silphium perfoliatum, Smallanthus uvedalia, Thymus marschallianus and Toona ciliata. It was first documented in 2000 (PMID: 11413487). This could make beta-bisabolene a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 22164802) (PMID: 23678435) (PMID: 23833899).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    0.8302    0.6976    2.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4134    0.4868    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9144   -0.0971    0.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8312    0.9592    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780    0.3537   -0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2195   -0.1974   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2459   -1.2692   -1.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4777    0.0917    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    0.7587   -0.1001 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4256   -0.4874   -0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7969   -0.8487   -1.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099   -0.5658   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1788   -0.9553   -0.8905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4941    0.1677    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6079    1.3237    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2043    0.4438    3.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979    1.1383    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9318   -0.9726    0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465   -0.3845    1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    1.2208   -0.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7338    1.9016    0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6843    1.0983    1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206   -1.6135   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523   -0.8555   -2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216   -2.1242   -0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5829    1.2094    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3395   -0.4194    0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4332   -0.2227    1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516    1.5638   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057   -1.3858   -0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990   -0.3551   -1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9694   -1.3622   -2.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1525   -1.8729   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6194   -0.1627   -1.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7732   -1.1090    0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069    0.5302    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827   -0.5148    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    2.1463    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0967    1.6843   -0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  5  2  3
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2  9  1  0
  9 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  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
  9 29  1  6
 15 38  1  0
 15 39  1  0
 14 36  1  0
 14 37  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 11 32  1  0
 10 30  1  0
 10 31  1  0
M  END

Bisabolen-beta
  Mrv1572001071617112D          

 15 15  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1  2  2  0  0  0  0
  3 11  1  0  0  0  0
  4  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  1  1  0  0  0  0
  5  6  1  0  0  0  0
  6  3  1  0  0  0  0
 11  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 14  1  0  0  0  0
 15 10  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0286921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(=C)C1CCC(C)=CC1

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

> <INCHI_KEY>
XZRVRYFILCSYSP-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.987960263211477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene

> <ALOGPS_LOGP>
6.01

> <JCHEM_LOGP>
4.879526926666667

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
70.2829

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-bisabolene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Bisabolen-beta                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
CONECT    1   13    2    5                                                  
CONECT    2    1    4                                                       
CONECT    3   11    4    6                                                  
CONECT    4    3    2                                                       
CONECT    5    1    6                                                       
CONECT    6    5    3                                                       
CONECT    7   11    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   14   15                                                  
CONECT   11    3    7   12                                                  
CONECT   12   11                                                            
CONECT   13    1                                                            
CONECT   14   10                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
beta-Bisabolen	ChEBI
b-Bisabolen	Generator
Β-bisabolen	Generator
b-Bisabolene	Generator
Β-bisabolene	Generator
1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexene, 9ci	HMDB
b-Limene	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene

Traditional Name

β-bisabolene

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(=C)C1CCC(C)=CC1

InChI Identifier

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

InChI Key

XZRVRYFILCSYSP-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
Abies alba	LOTUS Database	35616633
Abies sibirica	LOTUS Database	35616633
Ambrosia trifida	LOTUS Database	35616633
Avena fatua	LOTUS Database	35616633
Callitropsis nootkatensis	LOTUS Database	35616633
Cochlospermum tinctorium	LOTUS Database	35616633
Copaifera paupera	LOTUS Database	35616633
Helianthus tuberosus	LOTUS Database	35616633
Helichrysum argyrophyllum	LOTUS Database	35616633
Petasites albus	LOTUS Database	35616633
Petasites japonicus	LOTUS Database	35616633
Pimpinella anisum	LOTUS Database	35616633
Pinus pumila	LOTUS Database	35616633
Rattus rattus	LOTUS Database	35616633
Silphium perfoliatum	LOTUS Database	35616633
Smallanthus uvedalia	LOTUS Database	35616633
Thymus marschallianus	LOTUS Database	35616633
Toona ciliata	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
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

bisabolene (CHEBI:49249 )
a sesquiterpenoid (CPD-8246 )

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	6.01	ALOGPS
logP	4.88	ChemAxon
logS	-4.4	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	70.28 m³·mol⁻¹	ChemAxon
Polarizability	26.99 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

HMDB0035992

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014800

KNApSAcK ID

C00007242

Chemspider ID

357775

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

403919

PDB ID

Not Available

ChEBI ID

49249

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Okoh SO, Asekun OT, Familoni OB, Afolayan AJ: Composition and antioxidant activities of leaf and root volatile oils of Morinda lucida. Nat Prod Commun. 2011 Oct;6(10):1537-41. [PubMed:22164802 ]
Asnaashari S, Dadizadeh E, Talebpour AH, Eskandani M, Nazemiyeh H: Free Radical Scavenging Potential and Essential Oil Composition of the Dorema glabrum Fisch. C.A. Mey Roots from Iran. Bioimpacts. 2011;1(4):241-4. doi: 10.5681/bi.2011.035. Epub 2011 Dec 19. [PubMed:23678435 ]
Park YU, Koo HN, Kim GH: Chemical composition, larvicidal action, and adult repellency of Thymus magnus against Aedes albopictus. J Am Mosq Control Assoc. 2012 Sep;28(3):192-8. doi: 10.2987/12-6250R.1. [PubMed:23833899 ]
LOTUS database [Link]

Showing NP-Card for β-bisabolene (NP0286921)

MOL for NP0286921 (β-bisabolene)

3D MOL for NP0286921 (β-bisabolene)

3D SDF for NP0286921 (β-bisabolene)

3D-SDF for NP0286921 (β-bisabolene)

PDB for NP0286921 (β-bisabolene)

3D PDB for NP0286921 (β-bisabolene)

SMILES for NP0286921 (β-bisabolene)

INCHI for NP0286921 (β-bisabolene)

Structure for NP0286921 (β-bisabolene)

3D Structure for NP0286921 (β-bisabolene)