NP-MRD: Showing NP-Card for Taxicatin (NP0077776)

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Record Information

Version

2.0

Created at

2022-04-28 22:56:18 UTC

Updated at

2022-04-28 22:56:18 UTC

NP-MRD ID

NP0077776

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taxicatin

Description

SCHEMBL23457443 belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Taxicatin is found in Taxus baccata , Taxus canadensis and Taxus cuspidata. Based on a literature review very few articles have been published on SCHEMBL23457443.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -5.2010    2.6659   -1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1732    1.5475   -0.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155    0.8483   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1631   -0.2296    0.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0315   -0.9640    1.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2297   -2.0285    2.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -2.8900    2.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7996   -0.5888    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268    0.4810   -0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4277    0.8687   -0.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8332    0.3331   -0.5143 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7503    1.2157    0.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7581    0.4630    0.6388 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9666    1.3397    0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0003    0.6497    1.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1026   -0.7757   -0.1184 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4340   -1.1533    0.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -0.4880   -1.5951 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7614    0.5213   -2.0015 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4516   -0.1563   -1.8294 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7221   -1.2243   -2.3500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777    1.1939   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2594    2.7653   -1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8771    3.5970   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758    2.4257   -2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1324   -0.5118    1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2851   -2.3236    2.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0801   -3.7103    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5296   -3.3770    3.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9611   -1.1816    0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7795   -0.5414    0.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723    0.1635    1.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697    2.1651    1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3286    1.7943   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8654    0.7383    1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4888   -1.6581    0.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5296   -1.7009    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1097   -1.4353   -2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9759    0.4765   -2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.6785   -2.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440   -2.0333   -1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910    2.0402   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  2  0
 22  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9  8  2  0
  8  5  1  0
  5  6  1  0
  6  7  1  0
  5  4  2  0
  4  3  1  0
 20 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 42  1  0
 11 31  1  1
 13 32  1  1
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  1
 17 37  1  0
 18 38  1  6
 19 39  1  0
 20 40  1  6
 21 41  1  0
  8 30  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  4 26  1  0
M  END


  Mrv1652304292200562D          

 22 23  0  0  1  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    2.1434   -0.4125    0.0000 O   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
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  6  0  0  0
 14 21  1  6  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077776

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O8/c1-19-7-3-8(20-2)5-9(4-7)21-14-13(18)12(17)11(16)10(6-15)22-14/h3-5,10-18H,6H2,1-2H3/t10-,11+,12+,13-,14-/m1/s1

> <INCHI_KEY>
JDTIMXKVYWJWHE-MBJXGIAVSA-N

> <FORMULA>
C14H20O8

> <MOLECULAR_WEIGHT>
316.306

> <EXACT_MASS>
316.115817604

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.712459602600095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-(3,5-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-0.913730130333333

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196090132953177

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200138264434214

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437586387

> <JCHEM_POLAR_SURFACE_AREA>
117.84000000000002

> <JCHEM_REFRACTIVITY>
73.1097

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-(3,5-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   14   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀O₈

Average Mass

316.3060 Da

Monoisotopic Mass

316.11582 Da

IUPAC Name

(2S,3R,4S,5R,6R)-2-(3,5-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5R,6R)-2-(3,5-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1

InChI Identifier

InChI=1S/C14H20O8/c1-19-7-3-8(20-2)5-9(4-7)21-14-13(18)12(17)11(16)10(6-15)22-14/h3-5,10-18H,6H2,1-2H3/t10-,11+,12+,13-,14-/m1/s1

InChI Key

JDTIMXKVYWJWHE-MBJXGIAVSA-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
Taxus baccata	Plant	KNApSAcK
Taxus canadensis	Plant	KNApSAcK
Taxus cuspidata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-0.47	ALOGPS
logP	-0.91	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	117.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.11 m³·mol⁻¹	ChemAxon
Polarizability	30.71 Å³	ChemAxon
Number of Rings	2	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

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

142590310

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Taxicatin (NP0077776)

MOL for NP0077776 (Taxicatin)

3D MOL for NP0077776 (Taxicatin)

3D SDF for NP0077776 (Taxicatin)

3D-SDF for NP0077776 (Taxicatin)

PDB for NP0077776 (Taxicatin)

3D PDB for NP0077776 (Taxicatin)

SMILES for NP0077776 (Taxicatin)

INCHI for NP0077776 (Taxicatin)

Structure for NP0077776 (Taxicatin)

3D Structure for NP0077776 (Taxicatin)