NP-MRD: Showing NP-Card for 2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate (NP0171262)

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Record Information

Version

2.0

Created at

2022-09-03 07:42:24 UTC

Updated at

2022-09-03 07:42:24 UTC

NP-MRD ID

NP0171262

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate

Description

2-Hydroxy-3-(5-oxo-2,5-dihydrofuran-2-ylidene)propyl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. 2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate is found in Melodorum fruticosum. 2-Hydroxy-3-(5-oxo-2,5-dihydrofuran-2-ylidene)propyl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -5.2690    2.6504    0.9413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9822    1.5481    0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8516    0.4846   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1167   -0.5211   -0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165   -0.1580   -0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092   -0.9111   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301   -0.3652   -0.5590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3759    0.2158    0.6978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2765   -1.3919   -0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144   -0.9226   -0.5882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6171   -0.4028    0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9683   -0.3069    1.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9935    0.0443    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    0.5751    1.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9399    0.9945    1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6086    0.8650    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0126    0.3439   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939   -0.0691   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6811    1.0897    0.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9355    0.5296   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5155   -1.4300   -0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8453   -1.8754   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2386    0.4462   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8264   -0.3740    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -2.2857   -0.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353   -1.7783   -1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0908    0.6722    2.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4642    1.4118    2.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6544    1.1787    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5112    0.2301   -1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2210   -0.4879   -1.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  7  6  1  0
  6  5  2  0
  5 19  1  0
 19  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
 18 13  1  0
  4  5  1  0
  8 24  1  0
  7 23  1  6
  9 25  1  0
  9 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
  6 22  1  0
  3 20  1  0
  4 21  1  0
M  END


  Mrv1533004171512222D          

 19 20  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971   -2.3981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4491   -1.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2696   -1.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0366   -1.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296   -1.2420    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
 13  2  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171262

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(COC(=O)C1=CC=CC=C1)C=C1OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O5/c15-11(8-12-6-7-13(16)19-12)9-18-14(17)10-4-2-1-3-5-10/h1-8,11,15H,9H2

> <INCHI_KEY>
WQHRXHYOKDRIRR-UHFFFAOYSA-N

> <FORMULA>
C14H12O5

> <MOLECULAR_WEIGHT>
260.245

> <EXACT_MASS>
260.068473486

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.953718866232656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(5-oxo-2,5-dihydrofuran-2-ylidene)propyl benzoate

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
1.7276501553333334

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.947306484626374

> <JCHEM_PKA_STRONGEST_BASIC>
-3.259248143624424

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
69.24280000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.408  -4.476   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -6.438  -3.332   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.970  -3.493   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.668  -1.998   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.162  -2.318   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-3-(5-oxo-2,5-dihydrofuran-2-ylidene)propyl benzoic acid	Generator
2-Hydroxy-3-(5-oxofuran-2(5H)-ylidene)propyl benzoic acid	Generator

Chemical Formula

C₁₄H₁₂O₅

Average Mass

260.2450 Da

Monoisotopic Mass

260.06847 Da

IUPAC Name

2-hydroxy-3-(5-oxo-2,5-dihydrofuran-2-ylidene)propyl benzoate

Traditional Name

2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate

CAS Registry Number

Not Available

SMILES

OC(COC(=O)C1=CC=CC=C1)C=C1OC(=O)C=C1

InChI Identifier

InChI=1S/C14H12O5/c15-11(8-12-6-7-13(16)19-12)9-18-14(17)10-4-2-1-3-5-10/h1-8,11,15H,9H2

InChI Key

WQHRXHYOKDRIRR-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
Melodorum fruticosum	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
2-furanone
Dihydrofuran
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	1.6	ALOGPS
logP	1.73	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.95	ChemAxon
pKa (Strongest Basic)	-3.3	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	69.24 m³·mol⁻¹	ChemAxon
Polarizability	25.95 Å³	ChemAxon
Number of Rings	2	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

367556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate (NP0171262)

MOL for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

3D MOL for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

3D SDF for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

3D-SDF for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

PDB for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

3D PDB for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

SMILES for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

INCHI for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

Structure for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)

3D Structure for NP0171262 (2-hydroxy-3-(5-oxofuran-2-ylidene)propyl benzoate)