NP-MRD: Showing NP-Card for (z)-α-bisabolene (NP0178481)

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Record Information

Version

2.0

Created at

2022-09-03 16:28:59 UTC

Updated at

2022-09-03 16:28:59 UTC

NP-MRD ID

NP0178481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(z)-α-bisabolene

Description

2,7,10-Bisabolatriene, also known as cis-alpha-bisabolene or a-bisabolene?, Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, 2,7,10-bisabolatriene is considered to be an isoprenoid lipid molecule. The (Z)-stereoisomer of alpha-bisabolene. 2,7,10-Bisabolatriene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2,7,10-Bisabolatriene has been detected, but not quantified in, herbs and spices. (z)-α-bisabolene is found in Abies sibirica, Aloysia triphylla, Alpinia chinensis, Commiphora guidottii, Daucus carota, Eremanthus arboreus, Garcinia mangostana, Gossypium hirsutum, Grindelia hirsutula, Hedyosmum bonplandianum, Syzygiella autumnalis, Melissa officinalis, Osyris quadripartita, Picea schrenkiana, Plicanthus hirtellus, Pseudotsuga menziesii, Scapania crassiretis, Scapania undulata, Teucrium polium, Valeriana officinalis and Ziziphus jujuba. (z)-α-bisabolene was first documented in 2011 (PMID: 21823126). This could make 2,7,10-bisabolatriene a potential biomarker for the consumption of these foods (PMID: 23413580).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.5542   -1.0785    0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8704    0.0951    0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7432    0.9990    1.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5865    0.3397    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7290   -0.5503   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823    0.2908   -1.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1002    0.4965   -1.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679    1.3837   -2.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1388   -0.0478   -0.5632 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8686    1.1898    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981    0.7035    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -0.3979    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5883   -0.8709    1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3532   -1.1989   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1709   -0.8071   -1.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6371   -1.0673    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1348   -2.0123    0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4237   -1.0024   -0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5028    0.3658    2.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715    1.5740    2.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3044    1.6207    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430    1.1976    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -1.1083    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4372   -1.3284   -0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230    0.7559   -1.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362    2.3264   -2.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262    0.8292   -3.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354    1.5695   -2.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8087   -0.6557    0.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784    1.8450    0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710    1.7232   -0.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    1.2537    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5964   -0.8972    1.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5953   -0.2721    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3486   -1.9311    1.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3279   -2.2749   -0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2694   -1.0996   -1.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656   -1.7337   -1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4275   -0.2246   -2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  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
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  1
 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


  Mrv1652304272019002D          

 15 15  0  0  0  0            999 V2000
    2.0625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 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
  4 14  1  0  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  2  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  1  0  0  0  0
 11 15  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC\C=C(\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,5,9-11H2,1-4H3/b14-7-

> <INCHI_KEY>
YHBUQBJHSRGZNF-AUWJEWJLSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.244094640060247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.95

> <JCHEM_LOGP>
4.821593256333333

> <ALOGPS_LOGS>
-3.93

> <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>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z)-α-bisabolene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       3.850  -6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540  -5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.770  -1.334   0.000  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
cis-alpha-Bisabolene	ChEBI
cis-a-Bisabolene	Generator
cis-Α-bisabolene	Generator
1,8,12-Bisabolatriene	HMDB
4-(1,5-Dimethyl-1,4-hexadien-1-yl)-1-methyl-cyclohexene	HMDB
4-(1,5-Dimethyl-1,4-hexadienyl)-1-methyl-cyclohexene	HMDB
4-(1,5-Dimethyl-1,4-hexadienyl)-1-methylcyclohexene, 9ci	HMDB
4-(1,5-Dimethylhexa-1,4-dien-1-yl)-1-methylcyclohexene	HMDB
6-Methyl-2-(4-methylcyclohex-3-enyl)hept-2,5-diene	HMDB
a-Bisabolene?	HMDB
a-Limene	HMDB
alpha-Bisabolene	HMDB
Bisabola-4,7(11),9-triene	HMDB
FEMA 3331	HMDB
(Z)-a-Bisabolene	Generator
(Z)-Α-bisabolene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

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

Traditional Name

(Z)-α-bisabolene

CAS Registry Number

Not Available

SMILES

CC(C)=CC\C=C(\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,5,9-11H2,1-4H3/b14-7-

InChI Key

YHBUQBJHSRGZNF-AUWJEWJLSA-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 sibirica	LOTUS Database	35616633
Aloysia triphylla	LOTUS Database	35616633
Alpinia chinensis	LOTUS Database	35616633
Commiphora guidottii	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Eremanthus arboreus	LOTUS Database	35616633
Garcinia mangostana	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Grindelia hirsutula	LOTUS Database	35616633
Hedyosmum bonplandianum	LOTUS Database	35616633
Jamesoniella autumnalis	LOTUS Database	35616633
Melissa officinalis	LOTUS Database	35616633
Osyris quadripartita	LOTUS Database	35616633
Picea schrenkiana	LOTUS Database	35616633
Plicanthus hirtellus	LOTUS Database	35616633
Pseudotsuga menziesii	LOTUS Database	35616633
Scapania crassiretis	LOTUS Database	35616633
Scapania undulata	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Valeriana officinalis	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

alpha-bisabolene (CHEBI:49241 )
Bisabolane sesquiterpenoids (LMPR0103060006 )

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	5.95	ALOGPS
logP	4.82	ChemAxon
logS	-3.9	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	71.36 m³·mol⁻¹	ChemAxon
Polarizability	26.24 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

HMDB0035161

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014953

KNApSAcK ID

Not Available

Chemspider ID

4509521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352653

PDB ID

Not Available

ChEBI ID

49241

Good Scents ID

Not Available

References

General References

Xia Y, Zhang B, Li W, Xu G: Changes in volatile compound composition of Antrodia camphorata during solid state fermentation. J Sci Food Agric. 2011 Oct;91(13):2463-70. doi: 10.1002/jsfa.4488. Epub 2011 Aug 5. [PubMed:21823126 ]
Ogunwande IA, Jimoh R, Ajetunmobi AA, Avoseh NO, Flamini G: Essential oil composition of Ficus benjamina (Moraceae) and Irvingia barteri (Irvingiaceae). Nat Prod Commun. 2012 Dec;7(12):1673-5. [PubMed:23413580 ]
LOTUS database [Link]

Showing NP-Card for (z)-α-bisabolene (NP0178481)

MOL for NP0178481 ((z)-α-bisabolene)

3D MOL for NP0178481 ((z)-α-bisabolene)

3D SDF for NP0178481 ((z)-α-bisabolene)

3D-SDF for NP0178481 ((z)-α-bisabolene)

PDB for NP0178481 ((z)-α-bisabolene)

3D PDB for NP0178481 ((z)-α-bisabolene)

SMILES for NP0178481 ((z)-α-bisabolene)

INCHI for NP0178481 ((z)-α-bisabolene)

Structure for NP0178481 ((z)-α-bisabolene)

3D Structure for NP0178481 ((z)-α-bisabolene)