NP-MRD: Showing NP-Card for methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate (NP0252155)

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Record Information

Version

2.0

Created at

2022-09-07 15:34:49 UTC

Updated at

2022-09-07 15:34:49 UTC

NP-MRD ID

NP0252155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate

Description

Methyl 2-benzyl-4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate is found in Aspergillus flavipes. Based on a literature review very few articles have been published on Methyl 2-benzyl-4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    0.1564    4.1601   -1.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0602    3.4965   -0.6569 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2708    2.1296   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481    1.5240   -1.5729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825    1.4033    0.7486 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4497    0.7016    1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9854   -0.3011    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096   -1.6309    0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.6426   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -2.3068   -1.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3295   -0.9813   -1.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    0.0211   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313    2.4509    1.7313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026    2.3169    2.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    3.1071    3.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7576    1.1278    1.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572    0.6527    2.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0096    0.5919    0.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5003   -0.6691    0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803   -0.9505   -0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0498   -2.1950   -1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4468   -3.1752   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3714   -2.9022    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9141   -1.6907    1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601    5.1845   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1700    4.1704   -2.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    3.6691   -2.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2573    0.2384    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2433    1.4689    1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9410   -1.9403    1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185   -3.6806   -0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3355   -3.0887   -2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0156   -0.7072   -2.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1407    1.0354   -0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424    1.2807    2.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017   -0.2184   -1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0902   -2.3616   -2.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8083   -4.1337   -0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811   -3.6626    1.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613   -1.4926    2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 18  5  1  0
 24 19  1  0
 12  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 17 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
M  END


  Mrv1652309072217342D          

 24 26  0  0  0  0            999 V2000
    2.6255   -0.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0735   -0.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174    0.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347    0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203    1.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273    1.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4793    1.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    0.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 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
 16 18  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 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
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(CC2=CC=CC=C2)OC(=O)C(O)=C1C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O5/c1-23-18(22)19(12-13-8-4-2-5-9-13)15(16(20)17(21)24-19)14-10-6-3-7-11-14/h2-11,20H,12H2,1H3

> <INCHI_KEY>
ZBPZVOKACTVJJJ-UHFFFAOYSA-N

> <FORMULA>
C19H16O5

> <MOLECULAR_WEIGHT>
324.332

> <EXACT_MASS>
324.099773615

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.30841861310129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-benzyl-4-hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylate

> <JCHEM_LOGP>
3.4587823906666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.951824240326317

> <JCHEM_PKA_STRONGEST_BASIC>
-3.193872077281271

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
87.52310000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.901  -0.341   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.870  -1.486   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.364  -1.166   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.840   0.299   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.303  -1.166   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.779   0.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.251   1.444   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.225   2.908   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.731   3.228   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.761   2.084   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.285   0.619   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.580  -3.215   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.009  -5.926   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.342  -5.926   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.521  -3.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.986  -3.294   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.306  -1.788   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.162  -0.757   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.697  -1.233   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   13   18                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-benzyl-4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furoic acid	Generator

Chemical Formula

C₁₉H₁₆O₅

Average Mass

324.3320 Da

Monoisotopic Mass

324.09977 Da

IUPAC Name

methyl 2-benzyl-4-hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-carboxylate

Traditional Name

methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(CC2=CC=CC=C2)OC(=O)C(O)=C1C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H16O5/c1-23-18(22)19(12-13-8-4-2-5-9-13)15(16(20)17(21)24-19)14-10-6-3-7-11-14/h2-11,20H,12H2,1H3

InChI Key

ZBPZVOKACTVJJJ-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
Aspergillus flavipes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Monocyclic benzene moiety
2-furanone
Dicarboxylic acid or derivatives
Benzenoid
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Enol
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.46	ChemAxon
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.52 m³·mol⁻¹	ChemAxon
Polarizability	32.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

490310

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

563984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate (NP0252155)

MOL for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

3D MOL for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

3D SDF for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

3D-SDF for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

PDB for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

3D PDB for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

SMILES for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

INCHI for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

Structure for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)

3D Structure for NP0252155 (methyl 2-benzyl-4-hydroxy-5-oxo-3-phenylfuran-2-carboxylate)