NP-MRD: Showing NP-Card for tulsinol B (NP0038073)

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Record Information

Version

2.0

Created at

2021-06-20 20:51:41 UTC

Updated at

2021-06-30 00:10:39 UTC

NP-MRD ID

NP0038073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tulsinol B

Provided By

JEOL Database JEOL Logo

Description

(2S)-2beta-(3-Methoxy-4-hydroxyphenyl)-3alpha-(2-methoxy-4-allylphenoxy)-6-allyl-8-methoxy-3,4-dihydro-2H-1-benzopyran belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. tulsinol B is found in Tulsi (Ocimum sanctum L.). tulsinol B was first documented in 2009 (Suzuki, A., et al.). Based on a literature review very few articles have been published on (2S)-2beta-(3-Methoxy-4-hydroxyphenyl)-3alpha-(2-methoxy-4-allylphenoxy)-6-allyl-8-methoxy-3,4-dihydro-2H-1-benzopyran.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122513D          

 68 71  0  0  0  0            999 V2000
    1.0366   -3.5971   -6.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8763   -3.1020   -5.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5078    0.7709   -2.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122513D          

 68 71  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0038073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@]1([H])OC2=C(C([H])=C(C([H])=C2OC([H])([H])[H])C([H])([H])C([H])=C([H])[H])C([H])([H])[C@@]1([H])OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])C([H])=C([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O6/c1-6-8-19-10-13-24(26(15-19)33-4)35-28-18-22-14-20(9-7-2)16-27(34-5)30(22)36-29(28)21-11-12-23(31)25(17-21)32-3/h6-7,10-17,28-29,31H,1-2,8-9,18H2,3-5H3/t28-,29+/m1/s1

> <INCHI_KEY>
NMNZUBDWSACNNK-WDYNHAJCSA-N

> <FORMULA>
C30H32O6

> <MOLECULAR_WEIGHT>
488.58

> <EXACT_MASS>
488.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.974544797911534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxy-4-[(2S,3R)-8-methoxy-3-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-6-(prop-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]phenol

> <ALOGPS_LOGP>
5.84

> <JCHEM_LOGP>
6.764082268333333

> <ALOGPS_LOGS>
-6.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908203110826957

> <JCHEM_PKA_STRONGEST_BASIC>
-4.217401034836857

> <JCHEM_POLAR_SURFACE_AREA>
66.38000000000001

> <JCHEM_REFRACTIVITY>
140.28109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.26e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-4-[(2S,3R)-8-methoxy-3-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-6-(prop-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 35 65  1  0
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 35 67  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.037  -3.597  -6.235  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.876  -3.102  -5.316  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.553  -1.764  -5.417  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.203  -0.858  -4.261  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.999  -0.136  -4.264  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.659   0.680  -3.183  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.508   0.771  -2.080  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.103   1.584  -1.054  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.836   0.859   0.166  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.539   0.188   0.061  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.087  -0.211   1.399  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.163  -1.107   1.464  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.697  -1.497   2.698  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.845  -2.479   2.763  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.382  -3.874   3.072  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.785  -4.587   4.133  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.135  -0.987   3.879  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.068  -0.085   3.832  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.460   0.464   4.932  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.940   0.075   6.211  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.559   0.313   2.583  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.491   1.195   2.591  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.781   1.849   1.347  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.102   2.588   1.531  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.259   3.886   1.015  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.467   4.566   1.163  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.518   3.947   1.825  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.696   4.633   1.952  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.397   2.656   2.350  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.522   2.175   2.970  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.424   0.869   3.529  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.186   1.980   2.197  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.732   0.098  -2.094  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.625   0.200  -1.059  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.446   1.355  -1.247  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.064  -0.739  -3.161  0.00  0.00           C+0
HETATM   37  H   UNK     0       0.582  -4.574  -6.101  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.783  -3.045  -7.134  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.100  -3.697  -4.433  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.639  -1.921  -5.449  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.297  -1.259  -6.357  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.317  -0.215  -5.108  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.276   1.233  -3.196  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.598   0.097   0.377  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.461  -0.695  -0.586  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.253   0.869  -0.421  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.582  -1.509   0.543  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.573  -2.126   3.504  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.378  -2.490   1.804  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.676  -4.322   2.375  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.412  -5.594   4.298  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.489  -4.189   4.856  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.551  -1.316   4.826  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.984   0.374   6.348  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.811  -1.000   6.372  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.344   0.597   6.965  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.002   2.602   1.176  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.440   4.371   0.488  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.588   5.568   0.764  0.00  0.00           H+0
HETATM   60  H   UNK     0       6.277   4.033   2.460  0.00  0.00           H+0
HETATM   61  H   UNK     0       6.386   0.632   3.992  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.659   0.830   4.311  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.237   0.121   2.751  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.050   0.975   2.586  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.016   1.284  -2.180  0.00  0.00           H+0
HETATM   66  H   UNK     0       3.853   2.275  -1.237  0.00  0.00           H+0
HETATM   67  H   UNK     0       5.161   1.396  -0.421  0.00  0.00           H+0
HETATM   68  H   UNK     0       4.003  -1.286  -3.134  0.00  0.00           H+0
CONECT    1    2   37   38                                                  
CONECT    2    3    1   39                                                  
CONECT    3    4    2   40   41                                             
CONECT    4    5   36    3                                                  
CONECT    5    6    4   42                                                  
CONECT    6    7    5   43                                                  
CONECT    7    8    6   33                                                  
CONECT    8    9    7                                                       
CONECT    9   10   23    8   44                                             
CONECT   10   11    9   45   46                                             
CONECT   11   10   21   12                                                  
CONECT   12   13   11   47                                                  
CONECT   13   14   12   17                                                  
CONECT   14   13   15   48   49                                             
CONECT   15   14   16   50                                                  
CONECT   16   15   51   52                                                  
CONECT   17   13   18   53                                                  
CONECT   18   19   21   17                                                  
CONECT   19   18   20                                                       
CONECT   20   19   54   55   56                                             
CONECT   21   22   11   18                                                  
CONECT   22   21   23                                                       
CONECT   23    9   22   24   57                                             
CONECT   24   25   23   32                                                  
CONECT   25   24   26   58                                                  
CONECT   26   27   25   59                                                  
CONECT   27   28   29   26                                                  
CONECT   28   27   60                                                       
CONECT   29   30   32   27                                                  
CONECT   30   29   31                                                       
CONECT   31   30   61   62   63                                             
CONECT   32   24   29   64                                                  
CONECT   33   36    7   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   65   66   67                                             
CONECT   36    4   33   68                                                  
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    2                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   12                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   16                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   20                                                            
CONECT   57   23                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   28                                                            
CONECT   61   31                                                            
CONECT   62   31                                                            
CONECT   63   31                                                            
CONECT   64   32                                                            
CONECT   65   35                                                            
CONECT   66   35                                                            
CONECT   67   35                                                            
CONECT   68   36                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

RDKit          3D

68 71  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Value	Source
(2S)-2b-(3-Methoxy-4-hydroxyphenyl)-3a-(2-methoxy-4-allylphenoxy)-6-allyl-8-methoxy-3,4-dihydro-2H-1-benzopyran	Generator
(2S)-2Β-(3-methoxy-4-hydroxyphenyl)-3α-(2-methoxy-4-allylphenoxy)-6-allyl-8-methoxy-3,4-dihydro-2H-1-benzopyran	Generator

Chemical Formula

C₃₀H₃₂O₆

Average Mass

488.5800 Da

Monoisotopic Mass

488.21989 Da

IUPAC Name

2-methoxy-4-[(2S,3R)-8-methoxy-3-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-6-(prop-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]phenol

Traditional Name

2-methoxy-4-[(2S,3R)-8-methoxy-3-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]-6-(prop-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-2-yl]phenol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])[C@]1([H])OC2=C(C([H])=C(C([H])=C2OC([H])([H])[H])C([H])([H])C([H])=C([H])[H])C([H])([H])[C@@]1([H])OC1=C([H])C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])C([H])=C([H])[H]

InChI Identifier

InChI=1S/C30H32O6/c1-6-8-19-10-13-24(26(15-19)33-4)35-28-18-22-14-20(9-7-2)16-27(34-5)30(22)36-29(28)21-11-12-23(31)25(17-21)32-3/h6-7,10-17,28-29,31H,1-2,8-9,18H2,3-5H3/t28-,29+/m1/s1

InChI Key

NMNZUBDWSACNNK-WDYNHAJCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Ocimum tenuiflorum	JEOL database	Suzuki, A., et al, Chem. Pharm. Bull. 57, 245 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavan-3-ol
4'-hydroxyflavonoid
Hydroxyflavonoid
Monohydroxyflavonoid
Flavan
Benzopyran
Methoxyphenol
Chromane
1-benzopyran
Phenoxy compound
Phenol ether
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.84	ALOGPS
logP	6.76	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	140.28 m³·mol⁻¹	ChemAxon
Polarizability	54.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25231265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Suzuki, A., et al. (2009). Suzuki, A., et al, Chem. Pharm. Bull. 57, 245 (2009). Chem. Pharm. Bull..

Showing NP-Card for tulsinol B (NP0038073)

MOL for NP0038073 (tulsinol B)

3D MOL for NP0038073 (tulsinol B)

3D SDF for NP0038073 (tulsinol B)

3D-SDF for NP0038073 (tulsinol B)

PDB for NP0038073 (tulsinol B)

3D PDB for NP0038073 (tulsinol B)

SMILES for NP0038073 (tulsinol B)

INCHI for NP0038073 (tulsinol B)

Structure for NP0038073 (tulsinol B)

3D Structure for NP0038073 (tulsinol B)