NP-MRD: Showing NP-Card for Taxezopidine A (NP0079334)

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Record Information

Version

2.0

Created at

2022-04-29 00:22:00 UTC

Updated at

2022-04-29 00:22:00 UTC

NP-MRD ID

NP0079334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taxezopidine A

Description

(1R,3R,4R,5R,7R,10S,11R,12R,14S)-4,11-bis(acetyloxy)-1,7-dihydroxy-10,14,17-trimethyl-6-methylidene-16-oxatetracyclo[11.3.1.0³,¹⁴.0⁵,¹⁰]Heptadec-13(17)-en-12-yl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Taxezopidine A is found in Taxus cuspidata . Based on a literature review very few articles have been published on (1R,3R,4R,5R,7R,10S,11R,12R,14S)-4,11-bis(acetyloxy)-1,7-dihydroxy-10,14,17-trimethyl-6-methylidene-16-oxatetracyclo[11.3.1.0³,¹⁴.0⁵,¹⁰]Heptadec-13(17)-en-12-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202222D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292202222D          

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 26 29  1  1  0  0  0
  5 30  1  6  0  0  0
  3 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  1 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0079334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@@H]2C[C@@]3(O)OC[C@]2(C)C([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2(C)CC[C@@H](O)C(=C)[C@@H]12)=C3C

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O9/c1-12-18(30)8-9-24(6)19(12)21(33-14(3)27)17-10-26(31)13(2)20(25(17,7)11-32-26)22(34-15(4)28)23(24)35-16(5)29/h17-19,21-23,30-31H,1,8-11H2,2-7H3/t17-,18+,19-,21+,22+,23-,24-,25-,26+/m0/s1

> <INCHI_KEY>
OFABTNFZWMLARJ-QWHACPTKSA-N

> <FORMULA>
C26H36O9

> <MOLECULAR_WEIGHT>
492.565

> <EXACT_MASS>
492.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.158885859151184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,4R,5R,7R,10S,11R,12R,14S)-11,12-bis(acetyloxy)-1,7-dihydroxy-10,14,17-trimethyl-6-methylidene-16-oxatetracyclo[11.3.1.0^{3,14}.0^{5,10}]heptadec-13(17)-en-4-yl acetate

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
0.718831031

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.620332107960731

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.47018858194628

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9650013227749916

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
122.7242

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4R,5R,7R,10S,11R,12R,14S)-11,12-bis(acetyloxy)-1,7-dihydroxy-10,14,17-trimethyl-6-methylidene-16-oxatetracyclo[11.3.1.0^{3,14}.0^{5,10}]heptadec-13(17)-en-4-yl acetate

> <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      -0.048   0.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.786  -1.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.323  -1.493   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.669  -0.672   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.081   0.812   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.400   2.284   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.954   2.857   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.643   2.065   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.931   1.232   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.395  -0.637   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.320  -0.120   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.568  -0.958   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.354   0.356   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.012  -2.048   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.470   1.300   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.826   4.392   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.433   5.048   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.305   6.583   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.832   4.170   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.458   3.403   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.018   4.878   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.520   5.235   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.076   5.997   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.572   1.198   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.651   0.100   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.240  -1.384   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.749  -1.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.337  -3.254   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.319  -2.483   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.739   2.204   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.562  -3.015   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.365  -3.983   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.605  -5.504   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.073  -3.430   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.032   1.953   0.000  0.00  0.00           C+0
CONECT    1    2    8   13   35                                             
CONECT    2    1    3   11                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6   24   30                                             
CONECT    6    5    7   20                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    1    9                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12   14                                             
CONECT   11   10    2                                                       
CONECT   12   10   13                                                       
CONECT   13   12    1                                                       
CONECT   14   10                                                            
CONECT   15    9                                                            
CONECT   16    7   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    6   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    5   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26    4   28                                                  
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30    5                                                            
CONECT   31    3   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1R,3R,4R,5R,7R,10S,11R,12R,14S)-4,11-Bis(acetyloxy)-1,7-dihydroxy-10,14,17-trimethyl-6-methylidene-16-oxatetracyclo[11.3.1.0,.0,]heptadec-13(17)-en-12-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₆O₉

Average Mass

492.5650 Da

Monoisotopic Mass

492.23593 Da

IUPAC Name

(1R,3R,4R,5R,7R,10S,11R,12R,14S)-11,12-bis(acetyloxy)-1,7-dihydroxy-10,14,17-trimethyl-6-methylidene-16-oxatetracyclo[11.3.1.0^{3,14}.0^{5,10}]heptadec-13(17)-en-4-yl acetate

Traditional Name

(1R,3R,4R,5R,7R,10S,11R,12R,14S)-11,12-bis(acetyloxy)-1,7-dihydroxy-10,14,17-trimethyl-6-methylidene-16-oxatetracyclo[11.3.1.0^{3,14}.0^{5,10}]heptadec-13(17)-en-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@@H]2C[C@@]3(O)OC[C@]2(C)C([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2(C)CC[C@@H](O)C(=C)[C@@H]12)=C3C

InChI Identifier

InChI=1S/C26H36O9/c1-12-18(30)8-9-24(6)19(12)21(33-14(3)27)17-10-26(31)13(2)20(25(17,7)11-32-26)22(34-15(4)28)23(24)35-16(5)29/h17-19,21-23,30-31H,1,8-11H2,2-7H3/t17-,18+,19-,21+,22+,23-,24-,25-,26+/m0/s1

InChI Key

OFABTNFZWMLARJ-QWHACPTKSA-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 cuspidata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Pyran
Oxane
Cyclic alcohol
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.47	ALOGPS
logP	0.72	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.72 m³·mol⁻¹	ChemAxon
Polarizability	50.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162875521

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Taxezopidine A (NP0079334)

MOL for NP0079334 (Taxezopidine A)

3D MOL for NP0079334 (Taxezopidine A)

3D SDF for NP0079334 (Taxezopidine A)

3D-SDF for NP0079334 (Taxezopidine A)

PDB for NP0079334 (Taxezopidine A)

3D PDB for NP0079334 (Taxezopidine A)

SMILES for NP0079334 (Taxezopidine A)

INCHI for NP0079334 (Taxezopidine A)

Structure for NP0079334 (Taxezopidine A)

3D Structure for NP0079334 (Taxezopidine A)