NP-MRD: Showing NP-Card for [8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid (NP0197020)

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Record Information

Version

2.0

Created at

2022-09-04 15:12:41 UTC

Updated at

2022-09-04 15:12:42 UTC

NP-MRD ID

NP0197020

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid

Description

132616-54-7, Also known as bruceanic acid b, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. [8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid is found in Brucea antidysenterica. Based on a literature review very few articles have been published on 132616-54-7.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217122D          

 39 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042217122D          

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  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 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
 15 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 29 39  1  0  0  0  0
  5 39  1  0  0  0  0
  8 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197020

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12OCC34C1C(OC(=O)C1=CC=CC=C1)C(=O)OC3CC(C(C)=O)C(C)(CC(O)=O)C4C(O)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O12/c1-12(28)14-9-15-26-11-37-27(24(35)36-3,21(32)17(31)19(26)25(14,2)10-16(29)30)20(26)18(23(34)38-15)39-22(33)13-7-5-4-6-8-13/h4-8,14-15,17-21,31-32H,9-11H2,1-3H3,(H,29,30)

> <INCHI_KEY>
WPXXXQOSXRQJOB-UHFFFAOYSA-N

> <FORMULA>
C27H30O12

> <MOLECULAR_WEIGHT>
546.525

> <EXACT_MASS>
546.173726406

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.46994659159151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0^{1,6}.0^{2,13}]pentadecan-9-yl]acetic acid

> <JCHEM_LOGP>
0.09380723933333354

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.745532473971362

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.693682090824237

> <JCHEM_PKA_STRONGEST_BASIC>
-3.322124330376111

> <JCHEM_POLAR_SURFACE_AREA>
182.95999999999998

> <JCHEM_REFRACTIVITY>
127.10950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0^{1,6}.0^{2,13}]pentadecan-9-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.826   1.945   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.604   1.009   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.818   1.599   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.018   3.126   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.041   0.663   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.915  -0.276   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.048  -1.374   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.993  -0.708   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.132  -1.851   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.693  -1.755   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.362  -0.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.896  -0.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.542   1.164   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.784  -1.492   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.457   0.861   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.833   1.551   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.007   2.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.057   3.460   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.607   4.933   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.558   3.114   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.918   0.662   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.216   2.022   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.043   3.321   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.696   2.085   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.892   3.398   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.673  -3.324   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.172  -3.663   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.688  -5.125   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.179  -2.506   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.654  -2.721   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.078  -4.149   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.026  -5.362   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.447  -4.364   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.023  -5.792   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.548  -6.007   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.497  -4.794   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.921  -3.366   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.396  -3.151   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.895  -0.942   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24   39                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21   39                                             
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   15    8   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5   25                                                  
CONECT   25   24                                                            
CONECT   26    9   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   29    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Bruceanic acid b	MeSH

Chemical Formula

C₂₇H₃₀O₁₂

Average Mass

546.5250 Da

Monoisotopic Mass

546.17373 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C12OCC34C1C(OC(=O)C1=CC=CC=C1)C(=O)OC3CC(C(C)=O)C(C)(CC(O)=O)C4C(O)C2O

InChI Identifier

InChI=1S/C27H30O12/c1-12(28)14-9-15-26-11-37-27(24(35)36-3,21(32)17(31)19(26)25(14,2)10-16(29)30)20(26)18(23(34)38-15)39-22(33)13-7-5-4-6-8-13/h4-8,14-15,17-21,31-32H,9-11H2,1-3H3,(H,29,30)

InChI Key

WPXXXQOSXRQJOB-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
Brucea antidysenterica	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Benzoate ester
Furopyran
Benzoic acid or derivatives
Benzoyl
Delta_valerolactone
Delta valerolactone
Oxepane
Beta-hydroxy acid
Pyran
Hydroxy acid
Oxane
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Furan
Tetrahydrofuran
Methyl ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Ketone
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Ether
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
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	0.094	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

111689

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

125553

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid (NP0197020)

MOL for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

3D MOL for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

3D SDF for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

3D-SDF for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

PDB for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

3D PDB for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

SMILES for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

INCHI for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

Structure for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)

3D Structure for NP0197020 ([8-acetyl-3-(benzoyloxy)-11,12-dihydroxy-13-(methoxycarbonyl)-9-methyl-4-oxo-5,14-dioxatetracyclo[8.5.0.0¹,⁶.0²,¹³]pentadecan-9-yl]acetic acid)