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Showing NP-Card for Wyeronic acid (NP0337744)

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Record Information
Version2.0
Created at2024-09-11 12:11:31 UTC
Updated at2024-09-11 12:11:31 UTC
NP-MRD IDNP0337744
Secondary Accession NumbersNone
Natural Product Identification
Common NameWyeronic acid
DescriptionWyeronic acid, also known as wyeronate, belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid. Wyeronic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Wyeronic acid has been detected, but not quantified in, pulses. This could make wyeronic acid a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337744 (Wyeronic acid)


  Mrv0541 05061310522D          

 17 17  0  0  0  0            999 V2000
    4.1401    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    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
   -0.3297   -0.8227    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
    0.0059   -1.5764    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
    0.5678    1.9393    0.0000 C   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
    0.8264   -1.6626    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
    1.3113   -0.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -2.4163    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
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  3  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14 11  2  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
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3D MOL for NP0337744 (Wyeronic acid)

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3D SDF for NP0337744 (Wyeronic acid)

  Mrv0541 05061310522D          

 17 17  0  0  0  0            999 V2000
    4.1401    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    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
   -0.3297   -0.8227    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
    0.0059   -1.5764    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
    0.5678    1.9393    0.0000 C   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
    0.8264   -1.6626    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
    1.3113   -0.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -2.4163    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
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  3  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14 11  2  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H10O4/c1-2-3-4-5-11(14)12-8-6-10(17-12)7-9-13(15)16/h2-3,6-9H,1H3,(H,15,16)/b3-2+,9-7-

> <INCHI_KEY>
DMVOIMZYBMLJHN-XKURDXHJSA-N

> <FORMULA>
C13H10O4

> <MOLECULAR_WEIGHT>
230.2161

> <EXACT_MASS>
230.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.43708867250446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.4429427603333327

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.198642622020252

> <JCHEM_PKA_STRONGEST_BASIC>
-4.361006261705594

> <JCHEM_POLAR_SURFACE_AREA>
67.51

> <JCHEM_REFRACTIVITY>
64.6908

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337744 (Wyeronic acid)
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PDB for NP0337744 (Wyeronic acid)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.728   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.394   5.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.061   5.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.727   5.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.393   4.390   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      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.543  -3.104   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.448  -1.858   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.169  -4.510   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   11                                                       
CONECT    6    8   10                                                       
CONECT    7    9   10                                                       
CONECT    8    6   12                                                       
CONECT    9    7   13                                                       
CONECT   10    6    7   17                                                  
CONECT   11    5   12   14                                                  
CONECT   12    8   11   17                                                  
CONECT   13    9   15   16                                                  
CONECT   14   11                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

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3D PDB for NP0337744 (Wyeronic acid)
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SMILES for NP0337744 (Wyeronic acid)
C\C=C\C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O
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INCHI for NP0337744 (Wyeronic acid)
InChI=1S/C13H10O4/c1-2-3-4-5-11(14)12-8-6-10(17-12)7-9-13(15)16/h2-3,6-9H,1H3,(H,15,16)/b3-2+,9-7-
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View in JSmol
Synonyms
ValueSource
WyeronateGenerator
3-[5-(1-oxo-4-Hexen-2-ynyl)-2-furanyl]-2-propenoic acid, 9ciHMDB
(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoateGenerator
Chemical FormulaC13H10O4
Average Mass230.2161 Da
Monoisotopic Mass230.05791 Da
IUPAC Name(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid
Traditional Name(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
C\C=C\C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O
InChI Identifier
InChI=1S/C13H10O4/c1-2-3-4-5-11(14)12-8-6-10(17-12)7-9-13(15)16/h2-3,6-9H,1H3,(H,15,16)/b3-2+,9-7-
InChI KeyDMVOIMZYBMLJHN-XKURDXHJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentFuranoid fatty acids  
Alternative Parents
Substituents
  • Furanoid fatty acid
    • 

  • Aryl ketone
    • 

  • Furan
    • 

  • Heteroaromatic compound
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • 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
logP2.58ALOGPS
logP2.44ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.2ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.51 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.69 m³·mol⁻¹ChemAxon
Polarizability23.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039141  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018661  
KNApSAcK IDNot Available
Chemspider ID30777329  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752560  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available