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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:38 UTC
HMDB IDHMDB0059637
Secondary Accession Numbers
  • HMDB59637
Metabolite Identification
Common Name3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate
Description3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate, also known as hydroxydiiodophenylpyruvic acid, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. 3-(3,5-diiodo-4-hydroxyphenyl)pyruvate is part of the Citrate cycle (TCA cycle), Pyruvate metabolism, Glyoxylate and dicarboxylate metabolism, and Proximal tubule bicarbonate reclamation pathways. 3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563865958
Synonyms
ValueSource
3,5-Diiodo-4-hydroxyphenylpyruvateChEBI
beta-(3,5-Diiodo-4-hydroxyphenyl)pyruvateChEBI
3,5-Diiodo-4-hydroxyphenylpyruvic acidGenerator
b-(3,5-Diiodo-4-hydroxyphenyl)pyruvateGenerator
b-(3,5-Diiodo-4-hydroxyphenyl)pyruvic acidGenerator
beta-(3,5-Diiodo-4-hydroxyphenyl)pyruvic acidGenerator
Β-(3,5-diiodo-4-hydroxyphenyl)pyruvateGenerator
Β-(3,5-diiodo-4-hydroxyphenyl)pyruvic acidGenerator
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvic acidGenerator
(3,5-Diiodo-4-hydroxyphenyl)pyruvateHMDB
Hydroxydiiodophenylpyruvic acidHMDB
3-(3,5-diiodo-4-Hydroxyphenyl)pyruvateChEBI
Chemical FormulaC9H6I2O4
Average Molecular Weight431.9505
Monoisotopic Molecular Weight431.83554552
IUPAC Name3-(4-hydroxy-3,5-diiodophenyl)-2-oxopropanoic acid
Traditional Name3-(4-hydroxy-3,5-diiodophenyl)-2-oxopropanoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(=O)CC1=CC(I)=C(O)C(I)=C1
InChI Identifier
InChI=1S/C9H6I2O4/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,13H,3H2,(H,14,15)
InChI KeyTZPLBTUUWSVGCY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Phenylpyruvate
  • 3-phenylpropanoic-acid
  • 2-halophenol
  • 2-iodophenol
  • Phenol
  • Halobenzene
  • Iodobenzene
  • Alpha-keto acid
  • Aryl halide
  • Aryl iodide
  • Keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organohalogen compound
  • Organoiodide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.067 g/LALOGPS
logP3.19ALOGPS
logP3.45ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)1.55ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.42 m³·mol⁻¹ChemAxon
Polarizability27.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,1TMS,#12394.373https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,1TMS,#22405.9707https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,1TMS,#32506.5989https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,2TMS,#12465.9685https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,2TMS,#22496.2095https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,2TMS,#32545.8748https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,1TBDMS,#12647.0166https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,1TBDMS,#22681.959https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,1TBDMS,#32769.3855https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,2TBDMS,#12967.0925https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,2TBDMS,#22993.925https://arxiv.org/abs/1905.12712
3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate,2TBDMS,#33062.3118https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1009000000-478925321aeaed981ee02017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05ai-3100910000-45a5de75d45564776a0b2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08gr-0006900000-5bc80087ce697bb07e5b2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-0009300000-ef1eb19698da1f99209f2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0560-0019000000-5244a9c5f5f915de85ee2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1002900000-c80adf27818b330ae3d72017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06sr-1009500000-7011599ded17b2ee58e32017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-1049000000-905953b28ebe8ab1e8382017-10-06View Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01244
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound192726
PDB IDNot Available
ChEBI ID17131
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH1
Uniprot ID:
P40925
Molecular weight:
38627.255
Reactions
3-(3,5-Diiodo-4-hydroxyphenyl)lactate + NAD → 3-(3,5-Diiodo-4-hydroxyphenyl)pyruvate + NADHdetails