NP-MRD: Showing NP-Card for (5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid (NP0028277)

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Record Information

Version

2.0

Created at

2021-06-19 20:12:50 UTC

Updated at

2021-06-29 23:54:57 UTC

NP-MRD ID

NP0028277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid

Provided By

JEOL Database JEOL Logo

Description

(?)-Erigeronic acid A is also known as (?)-Erigeronate a. (5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid is found in Erigeron annuus. (5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid was first documented in 2002 (Oh, H., et al.). Based on a literature review very few articles have been published on (?)-Erigeronic acid A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122123D          

 28 28  0  0  0  0            999 V2000
    0.0485    0.9065    5.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    1.9024    4.3435 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3771    1.4595    2.8923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9970    2.4664    1.9201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8297    2.0399    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    1.6701   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    1.3657   -1.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    0.9035   -2.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675    1.6821   -1.4062 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2326    0.4675   -1.6785 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5750    0.3958   -3.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    1.3267   -3.9173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584   -0.8601   -3.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697    2.0437   -0.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.2427    6.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243    0.8020    5.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -0.0800    5.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1040    2.8848    4.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342    2.0078    4.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    1.3472    2.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    0.4735    2.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623    2.5895    2.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5317    3.4507    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    1.5845   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    2.5675   -1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1704    0.5216   -1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -0.4527   -1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -0.7745   -4.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 14  5  1  0  0  0  0
  4  3  1  0  0  0  0
  5  6  2  0  0  0  0
  3  2  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  2  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
  9 25  1  0  0  0  0
  6 24  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  2 18  1  0  0  0  0
  2 19  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
 10 26  1  0  0  0  0
 10 27  1  0  0  0  0
 13 28  1  0  0  0  0
M  END


  Mrv1652306192122123D          

 28 28  0  0  0  0            999 V2000
    0.0485    0.9065    5.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    1.9024    4.3435 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3771    1.4595    2.8923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9970    2.4664    1.9201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8297    2.0399    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8098    1.6701   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    1.3657   -1.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    0.9035   -2.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675    1.6821   -1.4062 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2326    0.4675   -1.6785 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5750    0.3958   -3.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    1.3267   -3.9173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584   -0.8601   -3.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697    2.0437   -0.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.2427    6.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243    0.8020    5.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -0.0800    5.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1040    2.8848    4.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342    2.0078    4.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    1.3472    2.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    0.4735    2.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623    2.5895    2.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5317    3.4507    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    1.5845   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    2.5675   -1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1704    0.5216   -1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -0.4527   -1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -0.7745   -4.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 14  5  1  0  0  0  0
  4  3  1  0  0  0  0
  5  6  2  0  0  0  0
  3  2  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  2  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
  9 25  1  0  0  0  0
  6 24  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  2 18  1  0  0  0  0
  2 19  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
 10 26  1  0  0  0  0
 10 27  1  0  0  0  0
 13 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@]1([H])OC(=C([H])C1=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O4/c1-2-3-4-7-5-8(11)9(14-7)6-10(12)13/h5,9H,2-4,6H2,1H3,(H,12,13)/t9-/m0/s1

> <INCHI_KEY>
SVNKCHWDJBIZMI-VIFPVBQESA-N

> <FORMULA>
C10H14O4

> <MOLECULAR_WEIGHT>
198.218

> <EXACT_MASS>
198.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.837019761210215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S)-5-butyl-3-oxo-2,3-dihydrofuran-2-yl]acetic acid

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.4972681903333336

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.19471224820178

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.344747055890969

> <JCHEM_PKA_STRONGEST_BASIC>
-4.840768749311799

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
51.08670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-5-butyl-3-oxo-2H-furan-2-yl]acetic 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       0.049   0.907   5.314  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.566   1.902   4.343  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.377   1.460   2.892  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.997   2.466   1.920  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.830   2.040   0.494  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.810   1.670  -0.327  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.095   1.366  -1.556  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.640   0.904  -2.546  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.368   1.682  -1.406  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.233   0.468  -1.679  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.575   0.396  -3.135  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.657   1.327  -3.917  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.858  -0.860  -3.530  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.470   2.044  -0.006  0.00  0.00           O+0
HETATM   15  H   UNK     0      -0.098   1.243   6.346  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.124   0.802   5.141  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.414  -0.080   5.210  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.104   2.885   4.496  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.634   2.008   4.565  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.694   1.347   2.682  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.837   0.474   2.747  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.062   2.590   2.152  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.532   3.451   2.053  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.868   1.585  -0.170  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.621   2.567  -1.998  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.170   0.522  -1.115  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.717  -0.453  -1.379  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.055  -0.775  -4.487  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    3    1   18   19                                             
CONECT    3    4    2   20   21                                             
CONECT    4    5    3   22   23                                             
CONECT    5    4   14    6                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14   25                                             
CONECT   10    9   11   26   27                                             
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   28                                                       
CONECT   14    5    9                                                       
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    2                                                            
CONECT   19    2                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    4                                                            
CONECT   24    6                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   10                                                            
CONECT   28   13                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Value	Source
(?)-erigeronate a	Generator

Chemical Formula

C₁₀H₁₄O₄

Average Mass

198.2180 Da

Monoisotopic Mass

198.08921 Da

IUPAC Name

2-[(2S)-5-butyl-3-oxo-2,3-dihydrofuran-2-yl]acetic acid

Traditional Name

[(2S)-5-butyl-3-oxo-2H-furan-2-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@]1([H])OC(=C([H])C1=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C10H14O4/c1-2-3-4-7-5-8(11)9(14-7)6-10(12)13/h5,9H,2-4,6H2,1H3,(H,12,13)/t9-/m0/s1

InChI Key

SVNKCHWDJBIZMI-VIFPVBQESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Erigeron annuus	JEOL database	Oh, H., et al, Phytochemistry 61, 175 (2002)

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

3-furanone
Vinylogous ester
Cyclic ketone
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	1.38	ALOGPS
logP	1.5	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.09 m³·mol⁻¹	ChemAxon
Polarizability	20.84 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

552351

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

636601

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Oh, H., et al. (2002). Oh, H., et al, Phytochemistry 61, 175 (2002). Phytochem..

Showing NP-Card for (5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid (NP0028277)

MOL for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

3D MOL for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

3D SDF for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

3D-SDF for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

PDB for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

3D PDB for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

SMILES for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

INCHI for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

Structure for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)

3D Structure for NP0028277 ((5-butyl-3-oxo-2,3-dihydrofuran-2-yl) acetic acid)