NP-MRD: Showing NP-Card for (+)-quebrachitol (NP0030103)

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Record Information

Version

2.0

Created at

2021-06-19 21:33:03 UTC

Updated at

2021-06-29 23:57:53 UTC

NP-MRD ID

NP0030103

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-quebrachitol

Provided By

JEOL Database JEOL Logo

Description

(-)-Bornesitol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring (-)-Bornesitol has been detected, but not quantified in, borages (Borago officinalis) and soy beans (Glycine max). This could make (-)-bornesitol a potential biomarker for the consumption of these foods (-)-Bornesitol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (+)-quebrachitol is found in Artemisia suksdorfii, Detarium microcarpum, Lathyrus odoratus, Platycladus orientalis and Trypanosoma brucei. (+)-quebrachitol was first documented in 2012 (PMID: 22333437). Based on a literature review a significant number of articles have been published on (-)-Bornesitol (PMID: 23413198) (PMID: 33113433) (PMID: 31787722) (PMID: 31171961) (PMID: 29980101) (PMID: 29281092).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123333D          

 27 27  0  0  0  0            999 V2000
   -0.2426    2.0452   -3.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    1.2081   -2.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314    0.1468   -2.2407 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2717    0.6703   -1.0292 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4879    1.3025   -1.4687 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6777   -0.4623   -0.0781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3360    0.1096    1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5186   -1.2930    0.3739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0418   -2.3659    1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2577   -1.8662   -0.8372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4079   -2.5801   -0.3565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956   -0.7571   -1.7934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6941    0.0366   -1.1205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8045    2.6114   -4.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118    2.7646   -3.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5233    1.4581   -4.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271   -0.4177   -2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2964    1.4438   -0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899    1.4777   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -1.1044   -0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4007   -0.6247    1.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873   -0.7013    1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7967   -2.9858    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246   -2.5959   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -1.9008   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2032   -1.1869   -2.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212    0.8164   -1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  6  1  0  0  0  0
  8 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12  3  1  0  0  0  0
 12 13  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
 10 11  1  0  0  0  0
 13 27  1  0  0  0  0
  3 17  1  6  0  0  0
  8 22  1  1  0  0  0
  9 23  1  0  0  0  0
 11 25  1  0  0  0  0
 12 26  1  6  0  0  0
  6 20  1  6  0  0  0
  7 21  1  0  0  0  0
  4 18  1  1  0  0  0
  5 19  1  0  0  0  0
 10 24  1  6  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
M  END


  Mrv1652306192123333D          

 27 27  0  0  0  0            999 V2000
   -0.2426    2.0452   -3.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    1.2081   -2.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314    0.1468   -2.2407 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2717    0.6703   -1.0292 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4879    1.3025   -1.4687 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6777   -0.4623   -0.0781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3360    0.1096    1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5186   -1.2930    0.3739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0418   -2.3659    1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2577   -1.8662   -0.8372 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4079   -2.5801   -0.3565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956   -0.7571   -1.7934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6941    0.0366   -1.1205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8045    2.6114   -4.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118    2.7646   -3.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5233    1.4581   -4.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271   -0.4177   -2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2964    1.4438   -0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899    1.4777   -0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -1.1044   -0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4007   -0.6247    1.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1873   -0.7013    1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7967   -2.9858    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246   -2.5959   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -1.9008   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2032   -1.1869   -2.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212    0.8164   -1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  6  1  0  0  0  0
  8 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12  3  1  0  0  0  0
 12 13  1  0  0  0  0
  8  9  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
 10 11  1  0  0  0  0
 13 27  1  0  0  0  0
  3 17  1  6  0  0  0
  8 22  1  1  0  0  0
  9 23  1  0  0  0  0
 11 25  1  0  0  0  0
 12 26  1  6  0  0  0
  6 20  1  6  0  0  0
  7 21  1  0  0  0  0
  4 18  1  1  0  0  0
  5 19  1  0  0  0  0
 10 24  1  6  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030103

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(OC([H])([H])[H])[C@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4+,5-,6-,7-/m1/s1

> <INCHI_KEY>
DSCFFEYYQKSRSV-AGZHHQKVSA-N

> <FORMULA>
C7H14O6

> <MOLECULAR_WEIGHT>
194.1825

> <EXACT_MASS>
194.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.17569025472244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol

> <ALOGPS_LOGP>
-2.67

> <JCHEM_LOGP>
-3.138883148333333

> <ALOGPS_LOGS>
0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.999964550804691

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.360891065931447

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6457717234067664

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
40.526199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-bornesitol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.243   2.045  -3.688  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.160   1.208  -2.994  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.531   0.147  -2.241  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.272   0.670  -1.029  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.488   1.303  -1.469  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.678  -0.462  -0.078  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.336   0.110   1.065  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.519  -1.293   0.374  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.042  -2.366   1.203  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.258  -1.866  -0.837  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.408  -2.580  -0.357  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.696  -0.757  -1.793  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.694   0.037  -1.121  0.00  0.00           O+0
HETATM   14  H   UNK     0      -0.805   2.611  -4.436  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.212   2.765  -3.003  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.523   1.458  -4.204  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.127  -0.418  -2.914  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.296   1.444  -0.499  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.990   1.478  -0.646  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.429  -1.104  -0.555  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.401  -0.625   1.710  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.187  -0.701   1.010  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.797  -2.986   1.277  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.625  -2.596  -1.355  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.108  -1.901  -0.253  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.203  -1.187  -2.665  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.821   0.816  -1.704  0.00  0.00           H+0
CONECT    1    2   14   15   16                                             
CONECT    2    1    3                                                       
CONECT    3    4   12    2   17                                             
CONECT    4    3    6    5   18                                             
CONECT    5    4   19                                                       
CONECT    6    4    8    7   20                                             
CONECT    7    6   21                                                       
CONECT    8    6   10    9   22                                             
CONECT    9    8   23                                                       
CONECT   10    8   12   11   24                                             
CONECT   11   10   25                                                       
CONECT   12   10    3   13   26                                             
CONECT   13   12   27                                                       
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    3                                                            
CONECT   18    4                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
CONECT   25   11                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3S,4S,5R,6S)-6-Methoxycyclohexane-1,2,3,4,5-pentol	ChEBI
1-O-Methyl-myo-inositol	ChEBI
Bornesitol	ChEBI
D-(-)-Bornesitol	ChEBI
1D-1-O-Methyl-myo-inositol	Kegg
D-1-O-Methyl-myo-inositol	HMDB
D-Bornesitol	HMDB
(-)-Bornesitol	ChEBI

Chemical Formula

C₇H₁₄O₆

Average Mass

194.1825 Da

Monoisotopic Mass

194.07904 Da

IUPAC Name

(1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol

Traditional Name

(-)-bornesitol

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(OC([H])([H])[H])[C@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4+,5-,6-,7-/m1/s1

InChI Key

DSCFFEYYQKSRSV-AGZHHQKVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia suksdorfii	JEOL database	Mahmoud, A. A., et al, Phytochemistry 67, 2103 (2006)
Borago officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cannabis sativa	CannabisDB	Not Available
Detarium microcarpum	LOTUS Database	35616633
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lathyrus odoratus	LOTUS Database	35616633
Marsdenia tomentosa	KNApSAcK Database	22123792
Platycladus orientalis	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

Alternative Parents

Substituents

Cyclohexanol
Cyclitol or derivatives
Cyclic alcohol
Polyol
Ether
Dialkyl ether
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

methyl myo-inositols (CHEBI:18427 )

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	-2.7	ALOGPS
logP	-3.1	ChemAxon
logS	0.45	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.53 m³·mol⁻¹	ChemAxon
Polarizability	18.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031437

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

1-METHYL-MYO-INOSITOL

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18427

Good Scents ID

rw1826531

References

General References

Pereira AB, Verissimo TM, Oliveira MA, Araujo IA, Alves RJ, Braga FC: Development and validation of an HPLC-DAD method for quantification of bornesitol in extracts from Hancornia speciosa leaves after derivatization with p-toluenesulfonyl chloride. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Mar 1;887-888:133-7. doi: 10.1016/j.jchromb.2012.01.009. Epub 2012 Jan 25. [PubMed:22333437 ]
Ruiz-Aceituno L, Rodriguez-Sanchez S, Ruiz-Matute AI, Ramos L, Soria AC, Sanz ML: Optimisation of a biotechnological procedure for selective fractionation of bioactive inositols in edible legume extracts. J Sci Food Agric. 2013 Aug 30;93(11):2797-803. doi: 10.1002/jsfa.6103. Epub 2013 Apr 9. [PubMed:23413198 ]
Moreira LN, Feltrin C, Goncalves JE, de Castro WV, Simoes CMO, de Padua RM, Cortes SF, Braga FC: Determination of l-(+)-bornesitol, the hypotensive constituent of Hancornia speciosa, in rat plasma by LC-MS/MS and its application on a pharmacokinetic study. Biomed Pharmacother. 2020 Dec;132:110900. doi: 10.1016/j.biopha.2020.110900. Epub 2020 Oct 28. [PubMed:33113433 ]
Moreira LN, Silva GC, Camara DV, Padua RM, Lemos VS, Braga FC, Cortes SF: The Cyclitol L-(+)-Bornesitol as an Active Marker for the Cardiovascular Activity of the Brazilian Medicinal Plant Hancornia speciosa. Biol Pharm Bull. 2019;42(12):2076-2082. doi: 10.1248/bpb.b19-00601. [PubMed:31787722 ]
Dohle W, Su X, Mills SJ, Rossi AM, Taylor CW, Potter BVL: A synthetic cyclitol-nucleoside conjugate polyphosphate is a highly potent second messenger mimic. Chem Sci. 2019 May 2;10(20):5382-5390. doi: 10.1039/C9SC00445A. Epub 2019 Apr 23. [PubMed:31171961 ]
Gomes JHS, da Silva GC, Cortes SF, de Padua RM, Braga FC: Forced degradation of l-(+)-bornesitol, a bioactive marker of Hancornia speciosa: Development and validation of stability indicating UHPLC-MS method and effect of degraded products on ACE inhibition. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Sep 1;1093-1094:31-38. doi: 10.1016/j.jchromb.2018.06.045. Epub 2018 Jun 22. [PubMed:29980101 ]
Wu ZC, Zhang JQ, Zhao JT, Li JG, Huang XM, Wang HC: Biosynthesis of quebrachitol, a transportable photosynthate, in Litchi chinensis. J Exp Bot. 2018 Mar 24;69(7):1649-1661. doi: 10.1093/jxb/erx483. [PubMed:29281092 ]
Mahmoud, A. A., et al. (2006). Mahmoud, A. A., et al, Phytochemistry 67, 2103 (2006). Phytochem..

Showing NP-Card for (+)-quebrachitol (NP0030103)

MOL for NP0030103 ((+)-quebrachitol)

3D MOL for NP0030103 ((+)-quebrachitol)

3D SDF for NP0030103 ((+)-quebrachitol)

3D-SDF for NP0030103 ((+)-quebrachitol)

PDB for NP0030103 ((+)-quebrachitol)

3D PDB for NP0030103 ((+)-quebrachitol)

SMILES for NP0030103 ((+)-quebrachitol)

INCHI for NP0030103 ((+)-quebrachitol)

Structure for NP0030103 ((+)-quebrachitol)

3D Structure for NP0030103 ((+)-quebrachitol)