NP-MRD: Showing NP-Card for methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate (NP0283068)

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Record Information

Version

2.0

Created at

2022-09-09 10:10:17 UTC

Updated at

2022-09-09 10:10:17 UTC

NP-MRD ID

NP0283068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate

Description

Methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]Pentadeca-1,3(7),8-triene-12-carboxylate belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton. methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate is found in Aglaia elaeagnoidea. Based on a literature review very few articles have been published on methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]Pentadeca-1,3(7),8-triene-12-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092212102D          

 40 45  0  0  0  0            999 V2000
   -2.0065   -3.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2597   -3.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8670   -2.0048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4432   -2.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821   -3.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0357   -3.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727   -4.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6345   -0.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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 37 38  2  0  0  0  0
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 35 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092212102D          

 40 45  0  0  0  0            999 V2000
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   -1.6555   -0.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198   -0.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    0.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1773    0.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131    0.0762    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 33  1  0  0  0  0
 25 34  1  0  0  0  0
  5 34  1  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
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C(OC(C)=O)C2(O)C3=C(OC2(C1C1=CC=CC=C1)C1=CC=C(OC)C=C1)C=C1OCOC1=C3OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H28O10/c1-16(31)39-27-22(28(32)36-4)23(17-8-6-5-7-9-17)30(18-10-12-19(34-2)13-11-18)29(27,33)24-20(40-30)14-21-25(26(24)35-3)38-15-37-21/h5-14,22-23,27,33H,15H2,1-4H3

> <INCHI_KEY>
ZWGZFGVICLTCML-UHFFFAOYSA-N

> <FORMULA>
C30H28O10

> <MOLECULAR_WEIGHT>
548.544

> <EXACT_MASS>
548.168247102

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.83623703899758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0^{3,7}.0^{10,14}]pentadeca-1(9),2,7-triene-12-carboxylate

> <JCHEM_LOGP>
3.1160462240000006

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.97540908683657

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.553049695132344

> <JCHEM_PKA_STRONGEST_BASIC>
-4.265471028138101

> <JCHEM_POLAR_SURFACE_AREA>
118.98000000000002

> <JCHEM_REFRACTIVITY>
137.8702

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0^{3,7}.0^{10,14}]pentadeca-1(9),2,7-triene-12-carboxylate

> <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      -3.745  -6.811   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.351  -6.157   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.221  -4.622   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.485  -3.742   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.827  -3.968   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.522  -4.711   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.713  -6.239   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.514  -7.169   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.933  -6.571   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.322  -8.697   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.645  -3.657   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.300  -5.051   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.173  -3.466   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.463  -1.953   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.918  -1.448   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.083  -2.455   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.793  -3.968   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.338  -4.473   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.048  -5.985   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.213  -6.993   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.142  -4.711   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.265  -3.657   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.611  -2.263   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.114  -1.210   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.991  -2.263   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.799  -0.735   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.620  -0.137   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.812   1.391   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.415   2.321   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.224   3.849   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.451   4.779   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.834   1.723   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.026   0.195   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.537  -2.455   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.591  -1.332   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.090  -1.682   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.144  -0.559   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.697   0.915   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.198   1.266   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.144   0.142   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   34                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13   25                                             
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16                                                       
CONECT   24   14   25                                                       
CONECT   25   24   11   26   34                                             
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   26                                                       
CONECT   34   25    5   35                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0,.0,]pentadeca-1,3(7),8-triene-12-carboxylic acid	Generator

Chemical Formula

C₃₀H₂₈O₁₀

Average Mass

548.5440 Da

Monoisotopic Mass

548.16825 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1C(OC(C)=O)C2(O)C3=C(OC2(C1C1=CC=CC=C1)C1=CC=C(OC)C=C1)C=C1OCOC1=C3OC

InChI Identifier

InChI=1S/C30H28O10/c1-16(31)39-27-22(28(32)36-4)23(17-8-6-5-7-9-17)30(18-10-12-19(34-2)13-11-18)29(27,33)24-20(40-30)14-21-25(26(24)35-3)38-15-37-21/h5-14,22-23,27,33H,15H2,1-4H3

InChI Key

ZWGZFGVICLTCML-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
Aglaia elaeagnoidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Flavaglines

Direct Parent

Flavaglines

Alternative Parents

Substituents

Flavagline skeleton
Stilbene
Benzodioxole
Coumaran
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Cyclic alcohol
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ether
Carboxylic acid derivative
Acetal
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
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

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

85183360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate (NP0283068)

MOL for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

3D MOL for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

3D SDF for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

3D-SDF for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

PDB for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

3D PDB for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

SMILES for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

INCHI for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

Structure for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)

3D Structure for NP0283068 (methyl 11-(acetyloxy)-10-hydroxy-8-methoxy-14-(4-methoxyphenyl)-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0³,⁷.0¹⁰,¹⁴]pentadeca-1(9),2,7-triene-12-carboxylate)