NP-MRD: Showing NP-Card for [(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid (NP0203431)

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Record Information

Version

2.0

Created at

2022-09-04 22:53:18 UTC

Updated at

2022-09-04 22:53:18 UTC

NP-MRD ID

NP0203431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid

Description

2-[(2E,4R)-3,5-dioxo-4-phenyloxolan-2-ylidene]-2-phenylacetic acid belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. [(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid is found in Pseudocyphellaria coronata. Based on a literature review very few articles have been published on 2-[(2E,4R)-3,5-dioxo-4-phenyloxolan-2-ylidene]-2-phenylacetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    1.0356   -0.2397    3.0873 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805   -0.0229    2.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1458    0.3399    2.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6397   -0.1194    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848   -0.4483    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162   -0.5252   -1.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9904   -0.8931   -1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5898   -0.9190   -2.4611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822   -1.2855   -0.0726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0055   -0.6176    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1071   -1.2848   -0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3474   -0.6651   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4395    0.5893    0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3234    1.2733    0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072    0.6416    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472   -0.7743    0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442   -0.6735    2.1552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7892    0.1931   -0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    0.9632   -1.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6738    1.2517   -2.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9445    0.7482   -1.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1135   -0.0175   -0.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512   -0.2985    0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110    1.2820    2.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7341   -2.3754   -0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0571   -2.2846   -0.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236   -1.2094   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3997    1.0467    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3884    2.2562    1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304    1.1723    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    1.3709   -1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565    1.8510   -2.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    0.9967   -2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0754   -0.4125   -0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980   -0.9097    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 16  1  0
 16 17  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16  5  1  0
 15 10  1  0
 23 18  1  0
  3 24  1  0
  9 25  1  6
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
 23 35  1  0
M  END


  Mrv1652309052200532D          

 23 25  0  0  1  0            999 V2000
    1.3222    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -4.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661   -3.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3188   -3.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  9 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 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
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(=C1\OC(=O)[C@@H](C1=O)C1=CC=CC=C1)\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O5/c19-15-13(11-7-3-1-4-8-11)18(22)23-16(15)14(17(20)21)12-9-5-2-6-10-12/h1-10,13H,(H,20,21)/b16-14+/t13-/m1/s1

> <INCHI_KEY>
HUIYQDPOQUVMPX-ZPTIMJQQSA-N

> <FORMULA>
C18H12O5

> <MOLECULAR_WEIGHT>
308.289

> <EXACT_MASS>
308.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.298634299480995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E,4R)-3,5-dioxo-4-phenyloxolan-2-ylidene]-2-phenylacetic acid

> <JCHEM_LOGP>
3.141332012666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.849826561050539

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.382133158980469

> <JCHEM_PKA_STRONGEST_BASIC>
-7.375076479446877

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
82.09900000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2E,4R)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       2.468   1.425   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.134  -0.885   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.048  -3.330   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.477  -6.041   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.127  -6.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.753  -7.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.848  -8.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.316  -8.532   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.310  -7.126   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.595  -5.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.091  -2.854   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.803   1.425   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   18                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    9    5   17                                                  
CONECT   17   16                                                            
CONECT   18    4   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
2-[(2E,4R)-3,5-Dioxo-4-phenyloxolan-2-ylidene]-2-phenylacetate	Generator

Chemical Formula

C₁₈H₁₂O₅

Average Mass

308.2890 Da

Monoisotopic Mass

308.06847 Da

IUPAC Name

2-[(2E,4R)-3,5-dioxo-4-phenyloxolan-2-ylidene]-2-phenylacetic acid

Traditional Name

[(2E,4R)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(=C1\OC(=O)[C@@H](C1=O)C1=CC=CC=C1)\C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H12O5/c19-15-13(11-7-3-1-4-8-11)18(22)23-16(15)14(17(20)21)12-9-5-2-6-10-12/h1-10,13H,(H,20,21)/b16-14+/t13-/m1/s1

InChI Key

HUIYQDPOQUVMPX-ZPTIMJQQSA-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
Pseudocyphellaria coronata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Furanones

Alternative Parents

Substituents

Monocyclic benzene moiety
Dicarboxylic acid or derivatives
3-furanone
Benzenoid
1,3-dicarbonyl compound
Enol ester
Oxolane
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	3.14	ChemAxon
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.1 m³·mol⁻¹	ChemAxon
Polarizability	30.3 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

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

163188067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid (NP0203431)

MOL for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

3D MOL for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

3D SDF for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

3D-SDF for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

PDB for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

3D PDB for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

SMILES for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

INCHI for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

Structure for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)

3D Structure for NP0203431 ([(2e,4r)-3,5-dioxo-4-phenyloxolan-2-ylidene](phenyl)acetic acid)