NP-MRD: Showing NP-Card for (+)-Taxiresinol (NP0054880)

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Record Information

Version

2.0

Created at

2022-04-28 01:05:29 UTC

Updated at

2022-04-28 01:05:29 UTC

NP-MRD ID

NP0054880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Taxiresinol

Description

Taxiresinol belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. Taxiresinol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-Taxiresinol is found in Daphne oleoides, Daphne oleoides spp. , Taxus baccata , Taxus cuspidata , Taxus mairei and Taxus wallichiana . (+)-Taxiresinol was first documented in 2003 (PMID: 14611890). Based on a literature review a significant number of articles have been published on taxiresinol (PMID: 21138310) (PMID: 25856716) (PMID: 22210027) (PMID: 21544613) (PMID: 20469636) (PMID: 19124280).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
    4.5813   -0.9565   -2.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127   -1.5118   -1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0821   -1.7701   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216   -1.5065   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -1.7859    0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5031   -1.4678    0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -0.1478    1.2424 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7605    0.9469    0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0014    1.1611   -0.6684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108    0.5342   -0.5591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3348    1.3558   -1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2771    0.7413   -1.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3604    1.4121   -2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5031    2.7539   -2.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5929    3.4257   -2.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5829    3.3878   -1.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7561    4.7376   -1.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4910    2.6934   -0.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    0.1996    0.8800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3507   -0.8548    1.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -1.0854    2.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710   -2.3524    1.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161   -2.6163    1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6136   -2.3337    0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9732   -2.6073    0.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2133   -1.3118   -3.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6157    0.1510   -2.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441   -1.2525   -2.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -1.0643   -1.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0240   -2.3277    1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -1.6124   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518   -0.0032    2.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046    0.6943    0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6794    1.8671    1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1367   -0.3934   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1882   -0.3158   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0714    0.8663   -3.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7066    4.3956   -2.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0982    5.2215   -0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7610    3.1806   -0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5903    1.1508    1.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -0.4416    0.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -1.8099    0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1011   -0.7312    3.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929   -2.5402    2.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2503   -3.0580    2.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3622   -3.0181    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
 10 11  1  0
 11 18  2  0
 18 16  1  0
 16 17  1  0
 16 14  2  0
 14 15  1  0
 14 13  1  0
 13 12  2  0
  5 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 19  7  1  0
 12 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  0
  8 34  1  0
 10 35  1  6
 19 41  1  1
 20 42  1  0
 20 43  1  0
 21 44  1  0
 18 40  1  0
 17 39  1  0
 15 38  1  0
 13 37  1  0
 12 36  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
M  END


  Mrv1652304282203052D          

 25 27  0  0  1  0            999 V2000
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032   -5.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
  3 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 20 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@H]2CO[C@@H]([C@H]2CO)C2=CC(O)=C(O)C=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O6/c1-24-18-7-11(2-4-16(18)22)6-13-10-25-19(14(13)9-20)12-3-5-15(21)17(23)8-12/h2-5,7-8,13-14,19-23H,6,9-10H2,1H3/t13-,14-,19+/m0/s1

> <INCHI_KEY>
SNZZAHRDXCGWEM-CKFHNAJUSA-N

> <FORMULA>
C19H22O6

> <MOLECULAR_WEIGHT>
346.379

> <EXACT_MASS>
346.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.51652581613792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
2.1594162590000003

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.299109501084361

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.176662654366591

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6393326871691514

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
92.71130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.104  -4.680   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.697  -1.233   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.057  -9.663   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.006  -9.985   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12                                                            
CONECT   18    3   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21                                                            
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₆

Average Mass

346.3790 Da

Monoisotopic Mass

346.14164 Da

IUPAC Name

4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]benzene-1,2-diol

Traditional Name

4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(C[C@H]2CO[C@@H]([C@H]2CO)C2=CC(O)=C(O)C=C2)=CC=C1O

InChI Identifier

InChI=1S/C19H22O6/c1-24-18-7-11(2-4-16(18)22)6-13-10-25-19(14(13)9-20)12-3-5-15(21)17(23)8-12/h2-5,7-8,13-14,19-23H,6,9-10H2,1H3/t13-,14-,19+/m0/s1

InChI Key

SNZZAHRDXCGWEM-CKFHNAJUSA-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
Daphne oleoides	LOTUS Database	35616633
Daphne oleoides spp.	Plant	KNApSAcK
Taxus baccata	Plant	KNApSAcK
Taxus cuspidata	Plant	KNApSAcK
Taxus mairei	Plant	KNApSAcK
Taxus wallichiana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,9'-epoxylignans

Alternative Parents

Substituents

7,9p-epoxylignan
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Catechol
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

polyphenol (CHEBI:70197 )
monomethoxybenzene (CHEBI:70197 )
tetrol (CHEBI:70197 )
oxolanes (CHEBI:70197 )
lignan (CHEBI:70197 )

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	1.8	ALOGPS
logP	2.16	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	92.71 m³·mol⁻¹	ChemAxon
Polarizability	36.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007200

Chemspider ID

8264500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10088963

PDB ID

Not Available

ChEBI ID

70197

Good Scents ID

Not Available

References

General References

Tezuka Y, Morikawa K, Li F, Auw L, Awale S, Nobukawa T, Kadota S: Cytochrome P450 3A4 inhibitory constituents of the wood of Taxus yunnanensis. J Nat Prod. 2011 Jan 28;74(1):102-5. doi: 10.1021/np100665j. Epub 2010 Dec 7. [PubMed:21138310 ]
Kupeli E, Erdemoglu N, Yesilada E, Sener B: Anti-inflammatory and antinociceptive activity of taxoids and lignans from the heartwood of Taxus baccata L. J Ethnopharmacol. 2003 Dec;89(2-3):265-70. doi: 10.1016/j.jep.2003.09.005. [PubMed:14611890 ]
Ahmad I, Waheed A, Tahir NB, Rais AK: Anti-inflammatory constituents from Perovskia atriplicifolia. Pharm Biol. 2015;53(11):1628-31. doi: 10.3109/13880209.2014.997250. Epub 2015 Apr 9. [PubMed:25856716 ]
Lee DG, Lee SM, Bang MH, Park HJ, Lee TH, Kim YH, Kim JY, Baek NI: Lignans from the flowers of Osmanthus fragrans var. aurantiacus and their inhibition effect on NO production. Arch Pharm Res. 2011 Dec;34(12):2029-35. doi: 10.1007/s12272-011-1204-y. Epub 2011 Dec 31. [PubMed:22210027 ]
Bulgakov VP, Tchernoded GK, Veselova MV, Fedoreyev SA, Muzarok TI, Zhuravlev YN: Catechin production in cultured cells of Taxus cuspidata and Taxus baccata. Biotechnol Lett. 2011 Sep;33(9):1879-83. doi: 10.1007/s10529-011-0632-6. Epub 2011 May 5. [PubMed:21544613 ]
Kucukboyaci N, Orhan I, Sener B, Nawaz SA, Choudhary MI: Assessment of enzyme inhibitory and antioxidant activities of lignans from Taxus baccata L. Z Naturforsch C J Biosci. 2010 Mar-Apr;65(3-4):187-94. doi: 10.1515/znc-2010-3-404. [PubMed:20469636 ]
Koyama J, Takeuchi A, Tode C, Shimizu M, Morita I, Nobukawa M, Nobukawa M, Kobayashi N: Development of an LC-ESI-MS/MS method for the determination of histamine: application to the quantitative measurement of histamine degranulation by KU812 cells. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jan 15;877(3):207-12. doi: 10.1016/j.jchromb.2008.12.012. Epub 2008 Dec 11. [PubMed:19124280 ]
Koyama J, Morita I, Kobayashi N, Hirai K, Simamura E, Nobukawa T, Kadota S: Antiallergic activity of aqueous extracts and constituents of Taxus yunnanensis. Biol Pharm Bull. 2006 Nov;29(11):2310-2. doi: 10.1248/bpb.29.2310. [PubMed:17077536 ]
Banskota AH, Nguyen NT, Tezuka Y, Nobukawa T, Kadota S: Hypoglycemic effects of the wood of Taxus yunnanensis on streptozotocin-induced diabetic rats and its active components. Phytomedicine. 2006 Jan;13(1-2):109-14. doi: 10.1016/j.phymed.2004.01.015. Epub 2005 Aug 15. [PubMed:16360940 ]
Erdemoglu N, Sener B, Choudhary MI: Bioactivity of Lignans from Taxus baccata. Z Naturforsch C J Biosci. 2004 Jul-Aug;59(7-8):494-8. doi: 10.1515/znc-2004-7-807. [PubMed:15813367 ]
Gurbuz I, Erdemoglu N, Yesilada E, Sener B: Anti-ulcerogenic lignans from Taxus baccata L. Z Naturforsch C J Biosci. 2004 Mar-Apr;59(3-4):233-6. doi: 10.1515/znc-2004-3-420. [PubMed:15241933 ]
Nguyen NT, Banskota AH, Tezuka Y, Le Tran Q, Nobukawa T, Kurashige Y, Sasahara M, Kadota S: Hepatoprotective effect of taxiresinol and (7'R)-7'-hydroxylariciresinol on D-galactosamine and lipopolysaccharide-induced liver injury in mice. Planta Med. 2004 Jan;70(1):29-33. doi: 10.1055/s-2004-815451. [PubMed:14765289 ]
Chattopadhyay SK, Kumar TR, Maulik PR, Srivastava S, Garg A, Sharon A, Negi AS, Khanuja SP: Absolute configuration and anticancer activity of taxiresinol and related lignans of Taxus wallichiana. Bioorg Med Chem. 2003 Nov 17;11(23):4945-8. doi: 10.1016/j.bmc.2003.09.010. [PubMed:14604656 ]

Showing NP-Card for (+)-Taxiresinol (NP0054880)

MOL for NP0054880 ((+)-Taxiresinol)

3D MOL for NP0054880 ((+)-Taxiresinol)

3D SDF for NP0054880 ((+)-Taxiresinol)

3D-SDF for NP0054880 ((+)-Taxiresinol)

PDB for NP0054880 ((+)-Taxiresinol)

3D PDB for NP0054880 ((+)-Taxiresinol)

SMILES for NP0054880 ((+)-Taxiresinol)

INCHI for NP0054880 ((+)-Taxiresinol)

Structure for NP0054880 ((+)-Taxiresinol)

3D Structure for NP0054880 ((+)-Taxiresinol)