NP-MRD: Showing NP-Card for β-bisabolol (NP0220607)

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Record Information

Version

2.0

Created at

2022-09-05 21:58:20 UTC

Updated at

2022-09-05 21:58:20 UTC

NP-MRD ID

NP0220607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-bisabolol

Description

6-Epi-beta-bisabolol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 6-Epi-beta-bisabolol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6-Epi-beta-bisabolol has been detected, but not quantified in, citrus. β-bisabolol is found in Aster scaber, Atalantia buxifolia, Canella winterana, Citrus aurantium, Cymbopogon distans, Gossypium hirsutum, Hedychium spicatum, Matricaria chamomilla, Peperomia blanda, Santolina chamaecyparissus, Vitex agnus-castus, Vitex negundo and Zingiber officinale. This could make 6-epi-beta-bisabolol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
   -5.4839   -1.0525   -1.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4082   -0.3952   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6078    1.0149   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3305   -1.0960   -0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2265   -0.5290    0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030   -0.5758   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1775    0.0147    0.8534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1929    1.4495    1.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -0.1152    0.2973 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8452   -1.4503    0.0291 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323    0.3352    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8817   -0.1118    0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1314   -0.1036   -0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4974   -0.5585   -0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2098    0.3037   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8370    0.6860   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0715   -1.8627   -1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0886   -0.3266   -1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1667   -1.5342   -0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2617    1.2636    1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6867    1.2721   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1331    1.6770   -0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444   -2.1301   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765    0.4954    1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1541   -1.1563    1.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206    0.0465   -0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7345   -1.6198   -0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -0.5285    1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944    1.5331    2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    1.8189    0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611    2.1431    1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -1.9992    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692    1.4639    1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -0.0259    2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6014   -0.4226    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9089   -1.2746   -0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4679   -1.0389   -1.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1346    0.3435   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -0.5994   -2.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6453    1.0790   -2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    0.5413   -1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.7769   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  7  9  1  0
  9 10  1  6
  9 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 11  9  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  7 28  1  1
  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
 10 32  1  0
 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
M  END


  Mrv0541 02241207422D          

 16 16  0  0  0  0            999 V2000
   -1.2670    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814    1.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814    0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670    0.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525    0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525    1.2670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6959    0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    1.6795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8764    1.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5909    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054    1.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7344    1.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0199    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    0.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  6  1  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 13  1  1  0  0  0
 11 12  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  6 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0220607

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-12(2)6-5-7-14(4)15(16)10-8-13(3)9-11-15/h6,8,14,16H,5,7,9-11H2,1-4H3/t14-,15-/m0/s1

> <INCHI_KEY>
WTVHAMTYZJGJLJ-GJZGRUSLSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.285520762597063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol

> <ALOGPS_LOGP>
4.77

> <JCHEM_LOGP>
3.989919242666667

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.48635603639968383

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
72.1105

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol

> <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      -2.365   3.135   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.699   2.365   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.699   0.825   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.365   0.055   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.031   0.825   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.031   2.365   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.032   0.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.302   3.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.636   2.365   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.970   3.135   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.303   2.365   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.637   3.135   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.302   4.675   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.971   2.365   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.637   4.675   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.302   1.595   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8   16                                             
CONECT    7    3                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   14   15                                                  
CONECT   13    8                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
6-Epi-b-bisabolol	Generator
6-Epi-β-bisabolol	Generator
(-)-Epi-beta-bisabolol	HMDB
3-Cyclohexen-1-ol, 1-[(1R)-1,5-dimethyl-4-hexenyl]-4-methyl-, (1S)-rel- (9ci)	HMDB
Epi-beta-bisabolol	HMDB

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3663 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(1R)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol

Traditional Name

(1R)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H26O/c1-12(2)6-5-7-14(4)15(16)10-8-13(3)9-11-15/h6,8,14,16H,5,7,9-11H2,1-4H3/t14-,15-/m0/s1

InChI Key

WTVHAMTYZJGJLJ-GJZGRUSLSA-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
Aster scaber	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Canella winterana	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Cymbopogon distans	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Hedychium spicatum	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Peperomia blanda	LOTUS Database	35616633
Santolina chamaecyparissus	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633
Zingiber officinale	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

Not Available

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	4.77	ALOGPS
logP	3.99	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-0.49	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	72.11 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

HMDB0035364

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014037

KNApSAcK ID

Not Available

Chemspider ID

16737085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12300148

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for β-bisabolol (NP0220607)

MOL for NP0220607 (β-bisabolol)

3D MOL for NP0220607 (β-bisabolol)

3D SDF for NP0220607 (β-bisabolol)

3D-SDF for NP0220607 (β-bisabolol)

PDB for NP0220607 (β-bisabolol)

3D PDB for NP0220607 (β-bisabolol)

SMILES for NP0220607 (β-bisabolol)

INCHI for NP0220607 (β-bisabolol)

Structure for NP0220607 (β-bisabolol)

3D Structure for NP0220607 (β-bisabolol)