NP-MRD: Showing NP-Card for alpha-Bisabolol (NP0044893)

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Record Information

Version

2.0

Created at

2022-03-10 18:45:56 UTC

Updated at

2022-03-10 22:17:55 UTC

NP-MRD ID

NP0044893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Bisabolol

Description

Alpha-Bisabolol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenes 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), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ) 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. Epi-Alpha-Bisabolol is an isomer of Bisabolol. Bisabolol or more formally alpha-(‚Äö√†√≠)-bisabolol is a colorless viscous oil. Bisabolenes are present in the essential oils of German chamomile (PMID: 22096322 ), And of a wide variety of other plants including cubeb, lemon, oregano, and Cannabis sativa (PMID: 6991645 , 26657499 ). Various derivates of bisabolol also function as pheromones in different insects (PMID: 31659569 ). Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear (doi:10.3390/F11030290). Bisabolol has a weak sweet floral aroma and is used in various fragrances.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
    4.8933    0.4046   -0.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112    0.1821    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7834    1.2168    1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1439   -0.9197    0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549   -1.2195    1.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421   -1.4196    0.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -0.2449    0.1312 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8143    0.1970   -1.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0598    0.7854    1.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3231   -0.4930   -0.2807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8352    0.7794   -0.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652    1.2160   -0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175    0.3877    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3386    0.8771    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -1.0420    0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564   -0.9608    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8475    1.4954   -1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990   -0.2217   -1.8500 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9331    0.2589   -0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2548    0.9079    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    1.4375    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2578    2.1507    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3146   -1.6501   -0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5148   -2.1517    1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2066   -0.4166    1.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802   -2.3321    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1641   -1.6453    1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928    1.1256   -0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4479   -0.5883   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987    0.5807   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718    0.3434    1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033   -1.3027   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9121    0.6609   -2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    1.6383   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732    2.2792   -0.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6928    1.7353    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0901    0.0778    0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2149    1.2595    1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4970   -1.4635   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496   -1.6056    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697   -1.9970    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951   -0.3232    1.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 10  7  1  0
  7  8  1  0
  7  9  1  1
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
 11 10  1  0
 10 32  1  6
 16 41  1  0
 16 42  1  0
 15 39  1  0
 15 40  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 12 35  1  0
 11 33  1  0
 11 34  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  6 26  1  0
  6 27  1  0
  5 24  1  0
  5 25  1  0
  4 23  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
M  END

  Mrv1652303202019012D          

 17 17  0  0  0  0            999 V2000
 9999.629310000.4122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3439 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.057110000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7723 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.485510000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1987 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.485510001.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.040910001.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.216010001.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7712 9998.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6293 9999.5877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.200610000.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.486110000.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4861 9999.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2006 9998.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9151 9999.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.915110000.0006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  6  0  0  0
  1  9  1  1  0  0  0
  2  3  1  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
  5  7  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 17 11  1  1  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1

> <INCHI_KEY>
RGZSQWQPBWRIAQ-CABCVRRESA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.289460303145148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol

> <ALOGPS_LOGP>
4.76

> <JCHEM_LOGP>
3.911965512666667

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4708710633739094

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
72.1875

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisabolol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.9758667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3098666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.6408667.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.9758666.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8671.3068667.436   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8672.6388666.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.3068668.975   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.7438668.767   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8665.2038668.767   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8660.6408664.358   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0    8665.9758665.897   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    8663.3088667.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.9748666.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.9748665.128   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.3088664.358   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.6428665.128   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.6428666.668   0.000  0.00  0.00           C+0
CONECT    1    2    8    9   17                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10   14                                                            
CONECT   11   17                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   10                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16    1   11                                             
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
Levomenol	Kegg
(-)-a-Bisabolol	Generator
(-)-Α-bisabolol	Generator
Bisabolol, (-)-isomer	HMDB
Bisabolol	HMDB
a-Bisabolol	HMDB
Α-bisabolol	HMDB
(-)-(1's,2S)-alpha-Bisabolol	HMDB
(-)-(1's,2S)-Α-bisabolol	HMDB
(-)-(1’S,2S)-α-bisabolol	HMDB
(-)-(4S,8S)-alpha-Bisabolol	HMDB
(-)-(4S,8S)-Α-bisabolol	HMDB
(AlphaS,1S)-alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol	HMDB
(ΑS,1S)-α,4-dimethyl-α-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol	HMDB
alpha-(-)-Bisabolol	HMDB
L-alpha-Bisabolol	HMDB
L-Α-bisabolol	HMDB
Α-(-)-bisabolol	HMDB
(-)-alpha-Bisabolol	HMDB

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol

Traditional Name

bisabolol

CAS Registry Number

23089-26-1

SMILES

[H][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C

InChI Identifier

InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1

InChI Key

RGZSQWQPBWRIAQ-CABCVRRESA-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
Abies sibirica	LOTUS Database	35616633
Achillea nobilis	LOTUS Database	35616633
Ambrosia trifida	Plant	KNApSAcK
Atalantia monophylla	Plant	KNApSAcK
Cannabis sativa	NULL	Not Available
Eremanthus arboreus	LOTUS Database	35616633
Eremanthus erythropappus	LOTUS Database	35616633
Ferula hermonis	Plant	KNApSAcK
Lychnophora ericoides	Plant	KNApSAcK
Matricaria chamomilla	Plant	KNApSAcK
Merulius tremellosus	LOTUS Database	35616633
Osyris tenuifolia	Plant	KNApSAcK
Petasites albus	Plant	KNApSAcK
Petasites hybridus	Plant	KNApSAcK
Picea jezoensis	LOTUS Database	35616633
Pinus sibirica	LOTUS Database	35616633
Populus balsamifera	Plant	KNApSAcK
Santolina rosmarinifolia	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
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:125 )
Bisabolane sesquiterpenoids (C09621 )
Bisabolanes (C09621 )
Bisabolane sesquiterpenoids (LMPR0103060001 )

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	4.76	ALOGPS
logP	3.91	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-0.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.19 m³·mol⁻¹	ChemAxon
Polarizability	28.29 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

HMDB0036197

DrugBank ID

DB13153

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003103 C00011607

Chemspider ID

Not Available

KEGG Compound ID

C09621

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442343

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang CY, Seo MH, Lee SC: Male-Produced Aggregation Pheromone of the Sloe Bug, Dolycoris baccarum L. (Hemiptera: Heteroptera: Pentatomidae). J Chem Ecol. 2019 Oct;45(10):818-822. doi: 10.1007/s10886-019-01110-3. Epub 2019 Oct 28. [PubMed:31659569 ]

Showing NP-Card for alpha-Bisabolol (NP0044893)

MOL for NP0044893 (alpha-Bisabolol)

3D MOL for NP0044893 (alpha-Bisabolol)

3D SDF for NP0044893 (alpha-Bisabolol)

3D-SDF for NP0044893 (alpha-Bisabolol)

PDB for NP0044893 (alpha-Bisabolol)

3D PDB for NP0044893 (alpha-Bisabolol)

SMILES for NP0044893 (alpha-Bisabolol)

INCHI for NP0044893 (alpha-Bisabolol)

Structure for NP0044893 (alpha-Bisabolol)

3D Structure for NP0044893 (alpha-Bisabolol)