NP-MRD: Showing NP-Card for (r)-β-bisabolene (NP0194594)

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Record Information

Version

2.0

Created at

2022-09-04 12:16:38 UTC

Updated at

2022-09-04 12:16:38 UTC

NP-MRD ID

NP0194594

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(r)-β-bisabolene

Description

(R)-beta-bisabolene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (R)-beta-bisabolene is considered to be an isoprenoid. (r)-β-bisabolene is found in Abies nordmanniana, Abies sibirica, Achillea grandifolia, Achillea ptarmica, Aframomum angustifolium, Ageratum conyzoides, Aloysia gratissima, Alpinia chinensis, Alpinia conchigera, Alpinia galanga, Alpinia latilabris, Alpinia mutica, Ambrosia trifida, Angelica archangelica, Asarum asperum, Aster scaber, Atalantia buxifolia, Avena fatua, Betonica macrantha, Cannabis sativa, Cantinoa mutabilis, Carpesium abrotanoides, Centella asiatica, Chromolaena laevigata, Cinnamomum parthenoxylon, Cinnamomum sieboldii, Citrus aurantium, Citrus limon, Citrus medica, Cochlospermum tinctorium, Copaifera multijuga, Cryptomeria japonica, Curcuma longa, Curcuma pierreana, Cymbopogon martinii, Daucus carota, Elsholtzia ciliata, Encelia canescens, Eremanthus arboreus, Eryngium foetidum, Eupatorium cannabinum, Eupatorium capillifolium, Ferulago thirkeana, Hamamelis virginiana, Hedychium coronarium, Hedychium spicatum, Helianthus tuberosus, Helichrysum italicum, Syzygiella autumnalis, Juniperus comitana, Lantana strigocamara, Lavandula latifolia, Lepechinia chamaedryoides, Litsea glaucescens, Metacalypogeia alternifolia, Metacalypogeia cordifolia, Mosla cavaleriei, Myrrhis odorata, Myrtus communis, Nepeta nuda, Nepeta racemosa, Ocimum gratissimum, Ocimum selloi, Origanum cordifolium, Origanum majorana, Origanum onites, Origanum vulgare, Perilla frutescens, Petasites albus, Petasites japonicus, Petroselinum crispum, Phyla dulcis, Picea glehnii, Picea koraiensis, Pimpinella anisum, Pinus koraiensis, Pinus massoniana, Piper auritum, Piper guineense, Piper obliquum, Polygala senega, Porella vernicosa, Prangos heyniae, Psidium guajava, Pterocaulon virgatum, Ptychopetalum olacoides, Rhododendron mucronulatum, Salvia fruticosa, Salvia hydrangea, Santalum spicatum, Satureja spicigera, Senecio squalidus, Sideritis romana, Smallanthus uvedalia, Solanum tuberosum, Solidago canadensis, Spondias mombin, Swertia japonica, Tagetes lucida, Teucrium cyprium, Thymbra spicata, Thymus citriodorus, Thymus kotschyanus, Thymus longicaulis, Thymus vulgaris, Tilesia baccata, Tussilago farfara, Umbellularia californica, Valeriana officinalis, Vitex negundo, Wettsteinia schusteriana, Widdringtonia whytei, Zingiber officinale and Ziziphus jujuba. Based on a literature review very few articles have been published on (R)-beta-bisabolene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -0.3654   -1.8595   -1.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656   -1.0723   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762   -0.6460    0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2313   -0.9444    0.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681   -0.2978   -0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242    0.5195   -0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7742    1.1776   -1.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4573    0.7765    1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868   -0.6144   -0.4688 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6148    0.8823   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0655    1.2051   -0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528    0.3753    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3760    0.8203    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6501   -0.9978    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558   -1.0499    0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2909   -2.1674   -2.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3755   -2.2466   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229    0.4496    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -1.1529    1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3668   -2.0478    0.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6755   -0.5917    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282   -0.4174   -1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551    1.2995   -2.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5572    0.4890   -1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1654    2.1604   -1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6591   -0.1573    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4113    1.3368    1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7224    1.4322    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127   -1.0333   -1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2440    1.2465   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    1.3851    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3795    2.1901   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5600    1.6438   -0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0072   -0.0752   -0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5835    1.1252    1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467   -1.2057    1.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609   -1.7794   -0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076   -2.0339    1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9616   -0.2481    1.6059 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

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(R)-b-Bisabolene	Generator
(R)-Β-bisabolene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

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

Traditional Name

(R)-β-bisabolene

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(=C)[C@@H]1CCC(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/t15-/m0/s1

InChI Key

XZRVRYFILCSYSP-HNNXBMFYSA-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 nordmanniana	LOTUS Database	35616633
Abies sibirica	LOTUS Database	35616633
Achillea grandifolia	LOTUS Database	35616633
Achillea ptarmica	LOTUS Database	35616633
Aframomum angustifolium	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Aloysia gratissima	LOTUS Database	35616633
Alpinia chinensis	LOTUS Database	35616633
Alpinia conchigera	LOTUS Database	35616633
Alpinia galanga	LOTUS Database	35616633
Alpinia latilabris	LOTUS Database	35616633
Alpinia mutica	LOTUS Database	35616633
Ambrosia trifida	LOTUS Database	35616633
Angelica archangelica	LOTUS Database	35616633
Asarum asperum	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Avena fatua	LOTUS Database	35616633
Betonica macrantha	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Cantinoa mutabilis	LOTUS Database	35616633
Carpesium abrotanoides	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Chromolaena laevigata	LOTUS Database	35616633
Cinnamomum parthenoxylon	LOTUS Database	35616633
Cinnamomum sieboldii	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Citrus limon	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Cochlospermum tinctorium	LOTUS Database	35616633
Copaifera multijuga	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Curcuma longa	LOTUS Database	35616633
Curcuma pierreana	LOTUS Database	35616633
Cymbopogon martinii	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Elsholtzia ciliata	LOTUS Database	35616633
Encelia canescens	LOTUS Database	35616633
Eremanthus arboreus	LOTUS Database	35616633
Eryngium foetidum	LOTUS Database	35616633
Eupatorium cannabinum	LOTUS Database	35616633
Eupatorium capillifolium	LOTUS Database	35616633
Ferulago thirkeana	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Hedychium coronarium	LOTUS Database	35616633
Hedychium spicatum	LOTUS Database	35616633
Helianthus tuberosus	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Jamesoniella autumnalis	LOTUS Database	35616633
Juniperus comitana	LOTUS Database	35616633
Lantana strigocamara	LOTUS Database	35616633
Lavandula latifolia	LOTUS Database	35616633
Lepechinia chamaedryoides	LOTUS Database	35616633
Litsea glaucescens	LOTUS Database	35616633
Metacalypogeia alternifolia	LOTUS Database	35616633
Metacalypogeia cordifolia	LOTUS Database	35616633
Mosla cavaleriei	LOTUS Database	35616633
Myrrhis odorata	LOTUS Database	35616633
Myrtus communis	LOTUS Database	35616633
Nepeta nuda	LOTUS Database	35616633
Nepeta racemosa	LOTUS Database	35616633
Ocimum gratissimum	LOTUS Database	35616633
Ocimum selloi	LOTUS Database	35616633
Origanum cordifolium	LOTUS Database	35616633
Origanum majorana	LOTUS Database	35616633
Origanum onites	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Petasites albus	LOTUS Database	35616633
Petasites japonicus	LOTUS Database	35616633
Petroselinum crispum	LOTUS Database	35616633
Phyla dulcis	LOTUS Database	35616633
Picea glehnii	LOTUS Database	35616633
Picea koraiensis	LOTUS Database	35616633
Pimpinella anisum	LOTUS Database	35616633
Pinus koraiensis	LOTUS Database	35616633
Pinus massoniana	LOTUS Database	35616633
Piper auritum	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper obliquum	LOTUS Database	35616633
Polygala senega	LOTUS Database	35616633
Porella vernicosa	LOTUS Database	35616633
Prangos heyniae	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Pterocaulon virgatum	LOTUS Database	35616633
Ptychopetalum olacoides	LOTUS Database	35616633
Rhododendron mucronulatum	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Salvia hydrangea	LOTUS Database	35616633
Santalum spicatum	LOTUS Database	35616633
Satureja spicigera	LOTUS Database	35616633
Senecio squalidus	LOTUS Database	35616633
Sideritis romana	LOTUS Database	35616633
Smallanthus uvedalia	LOTUS Database	35616633
Solanum tuberosum	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Spondias mombin	LOTUS Database	35616633
Swertia japonica	LOTUS Database	35616633
Tagetes lucida	LOTUS Database	35616633
Teucrium cyprium	LOTUS Database	35616633
Thymbra spicata	LOTUS Database	35616633
Thymus citriodorus	LOTUS Database	35616633
Thymus kotschyanus	LOTUS Database	35616633
Thymus longicaulis	LOTUS Database	35616633
Thymus vulgaris	LOTUS Database	35616633
Tilesia baccata	LOTUS Database	35616633
Tussilago farfara	LOTUS Database	35616633
Umbellularia californica	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633
Wettsteinia schusteriana	LOTUS Database	35616633
Widdringtonia whytei	LOTUS Database	35616633
Zingiber officinale	LOTUS Database	35616633
Ziziphus jujuba	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

beta-bisabolene (CHEBI:49266 )
Bisabolane sesquiterpenoids (LMPR0103060014 )

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	4.88	ChemAxon
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	26.67 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

Not Available

Chemspider ID

61436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68128

PDB ID

Not Available

ChEBI ID

49266

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (r)-β-bisabolene (NP0194594)

MOL for NP0194594 ((r)-β-bisabolene)

3D MOL for NP0194594 ((r)-β-bisabolene)

3D SDF for NP0194594 ((r)-β-bisabolene)

3D-SDF for NP0194594 ((r)-β-bisabolene)

PDB for NP0194594 ((r)-β-bisabolene)

3D PDB for NP0194594 ((r)-β-bisabolene)

SMILES for NP0194594 ((r)-β-bisabolene)

INCHI for NP0194594 ((r)-β-bisabolene)

Structure for NP0194594 ((r)-β-bisabolene)

3D Structure for NP0194594 ((r)-β-bisabolene)