NP-MRD: Showing NP-Card for [(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate (NP0290626)

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Record Information

Version

2.0

Created at

2022-09-09 21:23:36 UTC

Updated at

2022-09-09 21:23:36 UTC

NP-MRD ID

NP0290626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate

Description

(3E,7E)-2alpha,10beta,13alpha,20-Tetraacetoxy-5alpha-hydroxy-3,8-secotaxa-3,7,11-triene-9-one belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. [(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate is found in Taxus mairei. Based on a literature review very few articles have been published on (3E,7E)-2alpha,10beta,13alpha,20-Tetraacetoxy-5alpha-hydroxy-3,8-secotaxa-3,7,11-triene-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223232D          

 38 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092223232D          

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    4.3164    0.9355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8742    0.2485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7248    2.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536    0.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  6  0  0  0
 22 36  1  0  0  0  0
 13 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290626

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC\C1=C/[C@H](OC(C)=O)[C@@H]2C[C@H](OC(C)=O)C(C)=C([C@@H](OC(C)=O)C(=O)\C(C)=C\C[C@@H]1O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O10/c1-14-9-10-22(33)20(13-35-16(3)29)11-24(37-18(5)31)21-12-23(36-17(4)30)15(2)25(28(21,7)8)27(26(14)34)38-19(6)32/h9,11,21-24,27,33H,10,12-13H2,1-8H3/b14-9+,20-11+/t21-,22-,23-,24-,27+/m0/s1

> <INCHI_KEY>
GENZOPXHIRNHCL-GMRVMXMKSA-N

> <FORMULA>
C28H38O10

> <MOLECULAR_WEIGHT>
534.602

> <EXACT_MASS>
534.246497424

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.13071156904065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,3E,5S,7E,10R,13S)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate

> <JCHEM_LOGP>
1.5642413633333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.493709875948522

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.92630431621133

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0256724432266298

> <JCHEM_POLAR_SURFACE_AREA>
142.5

> <JCHEM_REFRACTIVITY>
136.94250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,3E,5S,7E,10R,13S)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       9.870   7.301   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.126   5.833   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.716   4.084   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.621   5.308   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.798   3.554   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.517   1.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   0.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.207   0.413   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.639  -1.159   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.950  -2.764   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.374  -3.477   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.917  -3.976   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.437   1.746   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.897   1.746   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.127   3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.508   2.936   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.637   1.773   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.541   0.186   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.212   1.946   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.781   5.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.437   4.414   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.207   5.747   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.629   7.350   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.802   9.001   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.664  10.117   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.886  10.198   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.747   5.747   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.877   7.419   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.517   4.414   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.471   2.958   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.057   4.414   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.827   3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.057   1.746   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.098   0.464   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.086   4.713   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.140   1.605   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   36                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   36                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    6   35                                                  
CONECT   35   34                                                            
CONECT   36   22   13   37   38                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
(3E,7E)-2a,10b,13a,20-Tetraacetoxy-5a-hydroxy-3,8-secotaxa-3,7,11-triene-9-one	Generator
(3E,7E)-2Α,10β,13α,20-tetraacetoxy-5α-hydroxy-3,8-secotaxa-3,7,11-triene-9-one	Generator

Chemical Formula

C₂₈H₃₈O₁₀

Average Mass

534.6020 Da

Monoisotopic Mass

534.24650 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC\C1=C/[C@H](OC(C)=O)[C@@H]2C[C@H](OC(C)=O)C(C)=C([C@@H](OC(C)=O)C(=O)\C(C)=C\C[C@@H]1O)C2(C)C

InChI Identifier

InChI=1S/C28H38O10/c1-14-9-10-22(33)20(13-35-16(3)29)11-24(37-18(5)31)21-12-23(36-17(4)30)15(2)25(28(21,7)8)27(26(14)34)38-19(6)32/h9,11,21-24,27,33H,10,12-13H2,1-8H3/b14-9+,20-11+/t21-,22-,23-,24-,27+/m0/s1

InChI Key

GENZOPXHIRNHCL-GMRVMXMKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 mairei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Verticillane diterpenoid
Tetracarboxylic acid or derivatives
Alpha-acyloxy ketone
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.56	ChemAxon
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	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

100959012

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate (NP0290626)

MOL for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

3D MOL for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

3D SDF for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

3D-SDF for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

PDB for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

3D PDB for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

SMILES for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

INCHI for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

Structure for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)

3D Structure for NP0290626 ([(1r,2s,3e,5s,7e,10r,13s)-2,10,13-tris(acetyloxy)-5-hydroxy-8,12,15,15-tetramethyl-9-oxobicyclo[9.3.1]pentadeca-3,7,11-trien-4-yl]methyl acetate)