NP-MRD: Showing NP-Card for 3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid (NP0146201)

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Record Information

Version

2.0

Created at

2022-09-02 01:33:23 UTC

Updated at

2022-09-02 01:33:23 UTC

NP-MRD ID

NP0146201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid

Description

3-{4-[4-Ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl}propanoic acid belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid is found in Xylocarpus granatum. 3-{4-[4-Ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl}propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191522112D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191522112D          

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   -2.5070    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4783    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8362    2.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1366    2.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4081    2.4385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1653    3.6503    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
  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  0  0  0  0
  5  9  2  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  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  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
 27 31  1  0  0  0  0
 26 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC1C2=C(OC(=C2)C2=CC(=O)OC(C3=COC=C3)C2(C)CCC(O)=O)C(C)C(CC(=O)OC)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-7-36-27-18-12-21(37-25(18)16(2)19(28(27,3)4)13-23(32)34-6)20-14-24(33)38-26(17-9-11-35-15-17)29(20,5)10-8-22(30)31/h9,11-12,14-16,19,26-27H,7-8,10,13H2,1-6H3,(H,30,31)

> <INCHI_KEY>
LOSVYNNNYIQPGP-UHFFFAOYSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.51819662429867

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl}propanoic acid

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
4.288434780333332

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9524053019252574

> <JCHEM_PKA_STRONGEST_BASIC>
-2.600216194309053

> <JCHEM_POLAR_SURFACE_AREA>
125.41000000000001

> <JCHEM_REFRACTIVITY>
136.758

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4H-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2H-pyran-3-yl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.465   2.016   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.206  -0.054   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.483  -1.306   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.910   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.220  -0.564   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.990  -1.897   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.990   0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.220   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.990   3.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.521   3.598   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.842   5.105   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -7.508   5.875   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.363   4.844   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.680   2.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.626   3.643   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.374   2.920   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.428   4.459   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.122   5.275   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.762   4.552   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.175   6.814   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   12    4   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    7   22   32                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27                                                       
CONECT   32   26   21   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl}propanoate	Generator

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl}propanoic acid

Traditional Name

3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4H-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2H-pyran-3-yl}propanoic acid

CAS Registry Number

Not Available

SMILES

CCOC1C2=C(OC(=C2)C2=CC(=O)OC(C3=COC=C3)C2(C)CCC(O)=O)C(C)C(CC(=O)OC)C1(C)C

InChI Identifier

InChI=1S/C29H36O9/c1-7-36-27-18-12-21(37-25(18)16(2)19(28(27,3)4)13-23(32)34-6)20-14-24(33)38-26(17-9-11-35-15-17)29(20,5)10-8-22(30)31/h9,11-12,14-16,19,26-27H,7-8,10,13H2,1-6H3,(H,30,31)

InChI Key

LOSVYNNNYIQPGP-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
Xylocarpus granatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Tricarboxylic acid or derivatives
Dihydropyranone
Pyran
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen 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
logP	4.79	ALOGPS
logP	4.29	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.41 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	136.76 m³·mol⁻¹	ChemAxon
Polarizability	56.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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 3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid (NP0146201)

MOL for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

3D MOL for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

3D SDF for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

3D-SDF for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

PDB for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

3D PDB for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

SMILES for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

INCHI for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

Structure for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)

3D Structure for NP0146201 (3-{4-[4-ethoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4h-1-benzofuran-2-yl]-2-(furan-3-yl)-3-methyl-6-oxo-2h-pyran-3-yl}propanoic acid)