NP-MRD: Showing NP-Card for 4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid (NP0028883)

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Record Information

Version

2.0

Created at

2021-06-19 20:38:54 UTC

Updated at

2021-06-29 23:55:56 UTC

NP-MRD ID

NP0028883

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid

Provided By

JEOL Database JEOL Logo

Description

4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid is found in Phomopsis sp. Melilotus dentata. 4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid was first documented in 2005 (Dai, J., et al.). Based on a literature review very few articles have been published on 4-{5-[(1R)-1-hydroxyethyl]furan-2-yl}-4-oxobutanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122383D          

 27 27  0  0  0  0            999 V2000
    0.4450    1.7422   -4.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0094    2.4165   -2.9394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1039    1.6908   -2.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    2.4644   -1.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    3.4572   -1.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459    2.8855   -0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2156    1.5793   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339    0.5487    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679    0.7084    1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7683   -0.7637    0.6143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3675   -0.6472    1.2062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6120   -0.1761    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320   -0.7142   -0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894    0.9954    0.4921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    1.3092   -1.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694    0.7111   -4.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753    2.2845   -4.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828    1.6893   -4.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3668    3.4286   -3.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8052    0.7573   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458    4.4779   -1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3740    3.3722    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676   -1.1156   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3365   -1.5044    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158   -1.6260    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3529    0.0267    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226    1.3123   -0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0  0  0  0
 10 11  1  0  0  0  0
  7 15  1  0  0  0  0
 11 12  1  0  0  0  0
 15  4  1  0  0  0  0
 12 14  1  0  0  0  0
  4  5  2  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
 12 13  2  0  0  0  0
  7  8  1  0  0  0  0
  4  2  1  0  0  0  0
  2  1  1  0  0  0  0
  8 10  1  0  0  0  0
  2  3  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
 11 25  1  0  0  0  0
 11 26  1  0  0  0  0
 14 27  1  0  0  0  0
  2 19  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 20  1  0  0  0  0
M  END


  Mrv1652306192122383D          

 27 27  0  0  0  0            999 V2000
    0.4450    1.7422   -4.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0094    2.4165   -2.9394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1039    1.6908   -2.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    2.4644   -1.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    3.4572   -1.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459    2.8855   -0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2156    1.5793   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339    0.5487    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679    0.7084    1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7683   -0.7637    0.6143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3675   -0.6472    1.2062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6120   -0.1761    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320   -0.7142   -0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894    0.9954    0.4921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    1.3092   -1.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694    0.7111   -4.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753    2.2845   -4.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3828    1.6893   -4.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3668    3.4286   -3.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8052    0.7573   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458    4.4779   -1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3740    3.3722    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676   -1.1156   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3365   -1.5044    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158   -1.6260    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3529    0.0267    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226    1.3123   -0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0  0  0  0
 10 11  1  0  0  0  0
  7 15  1  0  0  0  0
 11 12  1  0  0  0  0
 15  4  1  0  0  0  0
 12 14  1  0  0  0  0
  4  5  2  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
 12 13  2  0  0  0  0
  7  8  1  0  0  0  0
  4  2  1  0  0  0  0
  2  1  1  0  0  0  0
  8 10  1  0  0  0  0
  2  3  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
 11 25  1  0  0  0  0
 11 26  1  0  0  0  0
 14 27  1  0  0  0  0
  2 19  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028883

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])C(=O)C1=C([H])C([H])=C(O1)[C@]([H])(O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c1-6(11)8-3-4-9(15-8)7(12)2-5-10(13)14/h3-4,6,11H,2,5H2,1H3,(H,13,14)/t6-/m1/s1

> <INCHI_KEY>
QZPMJUUYIRZJKD-ZCFIWIBFSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.201

> <EXACT_MASS>
212.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.845907439928595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{5-[(1R)-1-hydroxyethyl]furan-2-yl}-4-oxobutanoic acid

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-0.014770893333333257

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.592441434317372

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.036995943663326

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0949075330392537

> <JCHEM_POLAR_SURFACE_AREA>
87.74

> <JCHEM_REFRACTIVITY>
50.8572

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{5-[(1R)-1-hydroxyethyl]furan-2-yl}-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.445   1.742  -4.224  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.009   2.417  -2.939  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.104   1.691  -2.366  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.069   2.464  -1.915  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.904   3.457  -1.447  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.646   2.886  -0.381  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.216   1.579  -0.254  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.534   0.549   0.713  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.368   0.708   1.605  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.768  -0.764   0.614  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.368  -0.647   1.206  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.612  -0.176   0.167  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.832  -0.714  -0.907  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.189   0.995   0.492  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.307   1.309  -1.234  0.00  0.00           O+0
HETATM   16  H   UNK     0       0.769   0.711  -4.041  0.00  0.00           H+0
HETATM   17  H   UNK     0       1.275   2.285  -4.688  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.383   1.689  -4.939  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.367   3.429  -3.155  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.805   0.757  -2.305  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.946   4.478  -1.802  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.374   3.372   0.254  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.768  -1.116  -0.423  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.337  -1.504   1.191  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.016  -1.626   1.551  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.353   0.027   2.070  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.623   1.312  -0.336  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    4    1    3   19                                             
CONECT    3    2   20                                                       
CONECT    4   15    5    2                                                  
CONECT    5    4    6   21                                                  
CONECT    6    7    5   22                                                  
CONECT    7    6   15    8                                                  
CONECT    8    9    7   10                                                  
CONECT    9    8                                                            
CONECT   10   11    8   23   24                                             
CONECT   11   10   12   25   26                                             
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12   27                                                       
CONECT   15    7    4                                                       
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    3                                                            
CONECT   21    5                                                            
CONECT   22    6                                                            
CONECT   23   10                                                            
CONECT   24   10                                                            
CONECT   25   11                                                            
CONECT   26   11                                                            
CONECT   27   14                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Value	Source
4-{5-[(1R)-1-hydroxyethyl]furan-2-yl}-4-oxobutanoate	Generator
4-[5-(1-Hydroxyethyl)furan-2-yl]-4-oxobutanoate	Generator

Chemical Formula

C₁₀H₁₂O₅

Average Mass

212.2010 Da

Monoisotopic Mass

212.06847 Da

IUPAC Name

4-{5-[(1R)-1-hydroxyethyl]furan-2-yl}-4-oxobutanoic acid

Traditional Name

4-{5-[(1R)-1-hydroxyethyl]furan-2-yl}-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C([H])([H])C(=O)C1=C([H])C([H])=C(O1)[C@]([H])(O[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C10H12O5/c1-6(11)8-3-4-9(15-8)7(12)2-5-10(13)14/h3-4,6,11H,2,5H2,1H3,(H,13,14)/t6-/m1/s1

InChI Key

QZPMJUUYIRZJKD-ZCFIWIBFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phomopsis sp. Melilotus dentata	JEOL database	Dai, J., et al, Eur. J. Org. Chem. 2005, 4009

Chemical Taxonomy

Classification

Not classified

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	0.5	ALOGPS
logP	-0.015	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	50.86 m³·mol⁻¹	ChemAxon
Polarizability	20.85 Å³	ChemAxon
Number of Rings	1	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

75141168

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101472984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dai, J., et al. (2005). Dai, J., et al, Eur. J. Org. Chem. 2005, 4009. Eur. J. Org. Chem..

Showing NP-Card for 4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid (NP0028883)

MOL for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

3D MOL for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

3D SDF for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

3D-SDF for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

PDB for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

3D PDB for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

SMILES for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

INCHI for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

Structure for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)

3D Structure for NP0028883 (4-[5-(1-hydroxyethyl)furan-2-yl)-4-oxobutanoic acid)