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Showing NP-Card for Dihydroxyfumaric acid (NP0086853)

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Record Information
Version2.0
Created at2022-05-11 16:32:50 UTC
Updated at2022-05-11 16:32:51 UTC
NP-MRD IDNP0086853
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydroxyfumaric acid
DescriptionDihydroxyfumaric acid, also known as dihydroxyfumarate or DHF, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Dihydroxyfumaric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0086853 (Dihydroxyfumaric acid)


  Mrv0541 02231219202D          

 10  9  0  0  0  0            999 V2000
   25.7833   -5.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3543   -4.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0688   -3.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4978   -3.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9268   -4.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2121   -5.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7833   -4.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4978   -4.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0688   -4.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2121   -4.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  1  0  0  0  0
  4  8  2  0  0  0  0
  5 10  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for NP0086853 (Dihydroxyfumaric acid)

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3D SDF for NP0086853 (Dihydroxyfumaric acid)

  Mrv0541 02231219202D          

 10  9  0  0  0  0            999 V2000
   25.7833   -5.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3543   -4.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0688   -3.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4978   -3.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9268   -4.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2121   -5.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7833   -4.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4978   -4.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0688   -4.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2121   -4.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  1  0  0  0  0
  4  8  2  0  0  0  0
  5 10  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086853

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(O)=C(O)C(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H4O6/c5-1(3(7)8)2(6)4(9)10/h5,7-8H,(H,9,10)

> <INCHI_KEY>
KAPRQAPANAEVOD-UHFFFAOYSA-N

> <FORMULA>
C4H4O6

> <MOLECULAR_WEIGHT>
148.071

> <EXACT_MASS>
148.00078786

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
10.974930661109335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,4-trihydroxy-2-oxobut-3-enoic acid

> <ALOGPS_LOGP>
-1.37

> <JCHEM_LOGP>
-0.008821624666666639

> <ALOGPS_LOGS>
-1.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.0340720442942204

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.012753692787183

> <JCHEM_PKA_STRONGEST_BASIC>
-5.210875591973815

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
37.861000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroxy-fumaric acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0086853 (Dihydroxyfumaric acid)
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PDB for NP0086853 (Dihydroxyfumaric acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      48.129 -10.762   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      45.461  -9.222   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      46.795  -6.912   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      49.463  -6.912   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      52.130  -8.452   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      50.796 -10.762   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      48.129  -9.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.463  -8.452   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      46.795  -8.452   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      50.796  -9.222   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    8                                                            
CONECT    5   10                                                            
CONECT    6   10                                                            
CONECT    7    1    8    9                                                  
CONECT    8    4    7   10                                                  
CONECT    9    2    3    7                                                  
CONECT   10    5    6    8                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0086853 (Dihydroxyfumaric acid)
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SMILES for NP0086853 (Dihydroxyfumaric acid)
OC(O)=C(O)C(=O)C(O)=O
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INCHI for NP0086853 (Dihydroxyfumaric acid)
InChI=1S/C4H4O6/c5-1(3(7)8)2(6)4(9)10/h5,7-8H,(H,9,10)
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View in JSmol
Synonyms
ValueSource
DihydroxyfumarateGenerator
(2-)DihydroxyfumarateHMDB
(2E)-2,3-Dihydroxybut-2-enedioateHMDB
(2E)-2,3-Dihydroxybut-2-enedioic acidHMDB
3,4,4-Trihydroxy-2-oxobut-3-enoateHMDB
3,4,4-Trihydroxy-2-oxobut-3-enoic acidHMDB
DHFHMDB
Dihydroxy-fumarateHMDB
Chemical FormulaC4H4O6
Average Mass148.0710 Da
Monoisotopic Mass148.00079 Da
IUPAC Name3,4,4-trihydroxy-2-oxobut-3-enoic acid
Traditional Namedihydroxy-fumaric acid
CAS Registry NumberNot Available
SMILES
OC(O)=C(O)C(=O)C(O)=O
InChI Identifier
InChI=1S/C4H4O6/c5-1(3(7)8)2(6)4(9)10/h5,7-8H,(H,9,10)
InChI KeyKAPRQAPANAEVOD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassShort-chain keto acids and derivatives  
Direct ParentShort-chain keto acids and derivatives  
Alternative Parents
Substituents
  • Short-chain keto acid
    • 

  • Hydroxy fatty acid
    • 

  • Alpha-keto acid
    • 

  • Fatty acyl
    • 

  • Alpha-branched alpha,beta-unsaturated-ketone
    • 

  • Unsaturated fatty acid
    • 

  • Acryloyl-group
    • 

  • Alpha-hydroxy ketone
    • 

  • Vinylogous acid
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Enone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Polyol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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-1.4ALOGPS
logP-0.0088ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.01ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.86 m³·mol⁻¹ChemAxon
Polarizability10.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002050  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022816  
KNApSAcK IDNot Available
Chemspider ID8299  
KEGG Compound IDC00975  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6460  
PubChem Compound8618  
PDB IDNot Available
ChEBI ID4593  
Good Scents IDNot Available
References
General ReferencesNot Available