NP-MRD: Showing NP-Card for 2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate (NP0321758)

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Record Information

Version

2.0

Created at

2022-09-12 00:08:17 UTC

Updated at

2022-09-12 00:08:17 UTC

NP-MRD ID

NP0321758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

Description

2,7,9,10-Tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]Pentadeca-3,8,11-trien-13-yl acetate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate is found in Taxus canadensis. Based on a literature review very few articles have been published on 2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]Pentadeca-3,8,11-trien-13-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202082D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122202082D          

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    3.2704   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4113   -1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4113   -0.4377    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  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  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  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  4  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 33 39  1  0  0  0  0
 25 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2C(OC(C)=O)C=C(CO)C(O)CC(OC(C)=O)C(C)=C(OC(C)=O)C(OC(C)=O)C(=C1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O12/c1-14-25(38-16(3)32)12-24(36)20(13-30)9-26(39-17(4)33)22-10-21(37-15(2)31)11-23(29(22,7)8)28(41-19(6)35)27(14)40-18(5)34/h9,11,21-22,24-26,28,30,36H,10,12-13H2,1-8H3

> <INCHI_KEY>
BWLBQEAJMDEUDE-UHFFFAOYSA-N

> <FORMULA>
C29H40O12

> <MOLECULAR_WEIGHT>
580.627

> <EXACT_MASS>
580.251976728

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.36065981102344

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

> <JCHEM_LOGP>
-0.4352073693333349

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.254728499010167

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.353954877109683

> <JCHEM_PKA_STRONGEST_BASIC>
-2.765994887510801

> <JCHEM_POLAR_SURFACE_AREA>
171.95999999999998

> <JCHEM_REFRACTIVITY>
144.50630000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.185   5.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.415   3.795   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.875   3.795   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.185   2.461   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.495   1.127   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.035   1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.805   2.461   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.805  -0.206   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.955  -4.207   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.185  -5.541   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.415  -4.207   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.875  -4.207   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.105  -5.541   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.875  -6.875   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415  -6.875   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.105  -8.208   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.255  -1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.055  -2.874   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.105   2.461   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.565   2.461   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.795   1.127   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.795   3.795   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.234  -2.263   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.234  -0.817   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   34                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   39                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33    5   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   33   25   40   41                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

View in JSmol

Synonyms

Value	Source
2,7,9,10-Tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetic acid	Generator

Chemical Formula

C₂₉H₄₀O₁₂

Average Mass

580.6270 Da

Monoisotopic Mass

580.25198 Da

IUPAC Name

2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

Traditional Name

2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2C(OC(C)=O)C=C(CO)C(O)CC(OC(C)=O)C(C)=C(OC(C)=O)C(OC(C)=O)C(=C1)C2(C)C

InChI Identifier

InChI=1S/C29H40O12/c1-14-25(38-16(3)32)12-24(36)20(13-30)9-26(39-17(4)33)22-10-21(37-15(2)31)11-23(29(22,7)8)28(41-19(6)35)27(14)40-18(5)34/h9,11,21-22,24-26,28,30,36H,10,12-13H2,1-8H3

InChI Key

BWLBQEAJMDEUDE-UHFFFAOYSA-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 canadensis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Enol ester
Secondary alcohol
Carboxylic acid ester
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.44	ChemAxon
pKa (Strongest Acidic)	14.35	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	171.96 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	144.51 m³·mol⁻¹	ChemAxon
Polarizability	58.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

162938396

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate (NP0321758)

MOL for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

3D MOL for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

3D SDF for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

3D-SDF for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

PDB for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

3D PDB for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

SMILES for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

INCHI for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

Structure for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)

3D Structure for NP0321758 (2,7,9,10-tetrakis(acetyloxy)-5-hydroxy-4-(hydroxymethyl)-8,15,15-trimethylbicyclo[9.3.1]pentadeca-3,8,11-trien-13-yl acetate)