NP-MRD: Showing NP-Card for 5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate (NP0315586)

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Record Information

Version

2.0

Created at

2022-09-11 14:17:43 UTC

Updated at

2022-09-11 14:17:43 UTC

NP-MRD ID

NP0315586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate

Description

5-(Acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-7-yl benzoate belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). 5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate is found in Tripterygium wilfordii. 5-(Acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-7-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241503322D          

 36 39  0  0  0  0            999 V2000
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    3.2152   -0.1020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004241503322D          

 36 39  0  0  0  0            999 V2000
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   -1.0718   -1.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -0.8402    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  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  1  0  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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 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
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  8 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 12 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1CC(C)C23CC(CC(OC(=O)C4=CC=CC=C4)C2(C)C1OC(C)=O)C(C)(C)O3

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O7/c1-8-17(2)25(31)34-22-14-18(3)29-16-21(27(5,6)36-29)15-23(28(29,7)24(22)33-19(4)30)35-26(32)20-12-10-9-11-13-20/h9-13,17-18,21-24H,8,14-16H2,1-7H3

> <INCHI_KEY>
OIOVDTUFIONZMQ-UHFFFAOYSA-N

> <FORMULA>
C29H40O7

> <MOLECULAR_WEIGHT>
500.632

> <EXACT_MASS>
500.277403628

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.0908656090736

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate

> <ALOGPS_LOGP>
5.32

> <JCHEM_LOGP>
5.488846984999999

> <ALOGPS_LOGS>
-5.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.212879216504694

> <JCHEM_POLAR_SURFACE_AREA>
88.13000000000001

> <JCHEM_REFRACTIVITY>
132.84490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      10.755  -2.611   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.217  -2.692   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.379  -1.401   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.077  -0.029   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.841  -1.482   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.142  -2.854   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.002  -0.190   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.464  -0.271   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.767  -1.657   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.228  -1.751   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.575  -3.146   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.294  -0.483   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.177   0.245   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.089   0.802   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.401   2.263   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.200   2.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.900   3.761   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.063   5.054   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.764   6.425   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.475   4.975   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.176   3.603   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.714   3.525   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.551   4.817   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.850   6.188   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.312   6.267   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.054   0.988   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.788   2.341   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.625   1.035   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.343   2.398   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.882   2.457   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.703   1.154   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.600   3.820   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.397  -0.779   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.869  -0.328   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.001  -2.196   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.021  -1.568   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   26   36                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   16   12   27   28                                             
CONECT   27   26                                                            
CONECT   28   26    8   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   14   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   12                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
5-(Acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0,]dodecan-7-yl benzoic acid	Generator
5-(Acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoic acid	Generator

Chemical Formula

C₂₉H₄₀O₇

Average Mass

500.6320 Da

Monoisotopic Mass

500.27740 Da

IUPAC Name

5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate

Traditional Name

5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1CC(C)C23CC(CC(OC(=O)C4=CC=CC=C4)C2(C)C1OC(C)=O)C(C)(C)O3

InChI Identifier

InChI=1S/C29H40O7/c1-8-17(2)25(31)34-22-14-18(3)29-16-21(27(5,6)36-29)15-23(28(29,7)24(22)33-19(4)30)35-26(32)20-12-10-9-11-13-20/h9-13,17-18,21-24H,8,14-16H2,1-7H3

InChI Key

OIOVDTUFIONZMQ-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
Tripterygium wilfordii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Fatty acid ester
Oxepane
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	5.32	ALOGPS
logP	5.49	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.84 m³·mol⁻¹	ChemAxon
Polarizability	54.09 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate (NP0315586)

MOL for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D MOL for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D SDF for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D-SDF for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

PDB for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D PDB for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

SMILES for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

INCHI for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

Structure for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)

3D Structure for NP0315586 (5-(acetyloxy)-2,6,10,10-tetramethyl-4-[(2-methylbutanoyl)oxy]-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl benzoate)