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Showing NP-Card for 5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid (NP0278200)

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Record Information
Version2.0
Created at2022-09-09 03:08:44 UTC
Updated at2022-09-09 03:08:44 UTC
NP-MRD IDNP0278200
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid
Description(+)-Osbeckic acid belongs to the class of organic compounds known as furoic acids. These are organic compounds containing a furoic acid moiety, with a structure characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom. 5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid is found in Osbeckia chinensis. 5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid was first documented in 2010 (PMID: 20873790). Based on a literature review very few articles have been published on (+)-Osbeckic acid (PMID: 31125231).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0278200 (5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid)


  Mrv1652309092205082D          

 13 13  0  0  1  0            999 V2000
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
  4 13  1  0  0  0  0
M  END
Download

3D MOL for NP0278200 (5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    4.1460   -0.5068    0.0852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2350    0.3526   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5379    1.7012    0.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8265   -0.0424   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090   -1.3565   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0342   -1.3070   -0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094    0.0224   -0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744    0.6021   -0.6415 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8318    1.6119    0.2879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.4312   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8087   -1.4448   -1.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767   -0.2649    0.4948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7881    0.7162   -0.3258 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4976    2.0333   -0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198   -2.2661   -0.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6330   -2.1393   -0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    1.0676   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196    1.2592    1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4252    0.3927    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4 13  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 13  7  1  0
  9 18  1  0
  8 17  1  6
 12 19  1  0
  6 16  1  0
  5 15  1  0
  3 14  1  0
M  END
Download

3D SDF for NP0278200 (5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid)


  Mrv1652309092205082D          

 13 13  0  0  1  0            999 V2000
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
  4 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278200

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O6/c8-5(7(11)12)3-1-2-4(13-3)6(9)10/h1-2,5,8H,(H,9,10)(H,11,12)/t5-/m0/s1

> <INCHI_KEY>
UAFTYLJFMASQBP-YFKPBYRVSA-N

> <FORMULA>
C7H6O6

> <MOLECULAR_WEIGHT>
186.119

> <EXACT_MASS>
186.016437913

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.802834843158692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(S)-carboxy(hydroxy)methyl]furan-2-carboxylic acid

> <JCHEM_LOGP>
-0.46633367966666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.0293550340766306

> <JCHEM_PKA_STRONGEST_ACIDIC>
-6.6372147202461305

> <JCHEM_PKA_STRONGEST_BASIC>
6.24577908839865

> <JCHEM_POLAR_SURFACE_AREA>
107.97

> <JCHEM_REFRACTIVITY>
38.2284

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(S)-carboxy(hydroxy)methyl]furan-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0278200 (5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid)

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PDB for NP0278200 (5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.011  -2.943   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.052  -2.621   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.773   0.032   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7    4                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0278200 (5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid)
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SMILES for NP0278200 (5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid)
O[C@H](C(O)=O)C1=CC=C(O1)C(O)=O
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INCHI for NP0278200 (5-[(s)-carboxy(hydroxy)methyl]furan-2-carboxylic acid)
InChI=1S/C7H6O6/c8-5(7(11)12)3-1-2-4(13-3)6(9)10/h1-2,5,8H,(H,9,10)(H,11,12)/t5-/m0/s1
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View in JSmol
Synonyms
ValueSource
(+)-OsbeckateGenerator
Chemical FormulaC7H6O6
Average Mass186.1190 Da
Monoisotopic Mass186.01644 Da
IUPAC Name5-[(S)-carboxy(hydroxy)methyl]furan-2-carboxylic acid
Traditional Name5-[(S)-carboxy(hydroxy)methyl]furan-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@H](C(O)=O)C1=CC=C(O1)C(O)=O
InChI Identifier
InChI=1S/C7H6O6/c8-5(7(11)12)3-1-2-4(13-3)6(9)10/h1-2,5,8H,(H,9,10)(H,11,12)/t5-/m0/s1
InChI KeyUAFTYLJFMASQBP-YFKPBYRVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Osbeckia chinensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furoic acids. These are organic compounds containing a furoic acid moiety, with a structure characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassFurans  
Sub ClassFuroic acid and derivatives  
Direct ParentFuroic acids  
Alternative Parents
Substituents
  • Furoic acid
    • 

  • Alpha-hydroxy acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Hydroxy acid
    • 

  • Heteroaromatic compound
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aromatic alcohol
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.47ChemAxon
pKa (Strongest Acidic)-6.6ChemAxon
pKa (Strongest Basic)6.25ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area107.97 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.23 m³·mol⁻¹ChemAxon
Polarizability15.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID75158568  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13965144  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Murata T, Katagiri T, Ishikawa Y, Abe M, Takahashi E, Iwahana R, Sakamoto Y, Sasaki K: Inhibitory Effects of Phenylpropanoid Derivatives from Oenanthe javanica on Antigen-Stimulated Degranulation in RBL-2H3 Cells. J Nat Prod. 2019 Jun 28;82(6):1518-1526. doi: 10.1021/acs.jnatprod.8b01054. Epub  2019 May 24. [PubMed:31125231  ] 
  2. Matsui T, Kudo A, Tokuda S, Matsumoto K, Hosoyama H: Identification of a new natural vasorelaxatant compound, (+)-osbeckic acid, from rutin-free tartary buckwheat extract. J Agric Food Chem. 2010 Oct 27;58(20):10876-9. doi: 10.1021/jf1028416. Epub 2010  Sep 28. [PubMed:20873790  ] 
  3. LOTUS database [Link]