protoporphyrinogen IX (PAMDB110804)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110804
Identification
Name: protoporphyrinogen IX
Description:Dicarboxylate anion of protoporphyrinogen.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • protoporphyrinogen
Chemical Formula: C34H38N4O4
Average Molecular Weight: 566.7
Monoisotopic Molecular Weight: 568.3049557932
InChI Key: UHSGPDMIQQYNAX-UHFFFAOYSA-L
InChI: InChI=1S/C34H40N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,35-38H,1-2,9-16H2,3-6H3,(H,39,40)(H,41,42)/p-2
CAS number: 7412-77-3
IUPAC Name:3,3'-(8,13-diethynyl-3,7,12,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-diyl)dipropanoate
Traditional IUPAC Name: protoporphyrinogen
SMILES:C=CC1(=C5(NC(=C1C)CC2(=C(C(=C(N2)CC3(NC(=C(C=3CCC([O-])=O)C)CC4(=C(C(=C(N4)C5)C)C=C)))CCC(=O)[O-])C)))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as porphyrins. These are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassTetrapyrroles and derivatives
Direct Parent Porphyrins
Alternative Parents
Substituents
  • Porphyrin
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0055 mg/mLALOGPS
logP3.44ALOGPS
logP6.2ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area137.76 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity169.42 m3·mol-1ChemAxon
Polarizability64.5 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
coproporphyrinogen III + Oxygen + Hydrogen ion → protoporphyrinogen IX + Carbon dioxide + Water
protoporphyrinogen IX + Oxygen → protoporphyrin IX + Hydrogen peroxide
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000190000-7c4ce83e3be73bfccdf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-0000490000-affa2d20d85ce7a5a2a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-0020900000-a1714c4d96457c66da57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-4148fa37b5b91e3b5a92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05tb-1000090000-27a9f5ba745bc29e2b22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000260000-392765703d0911aa98fcView in MoNA
References
References:
  • Wan J, Zhang L, Yang G, Zhan CG: Quantitative structure-activity relationship for cyclic imide derivatives of protoporphyrinogen oxidase inhibitors: a study of quantum chemical descriptors from density functional theory. J Chem Inf Comput Sci. 2004 Nov-Dec;44(6):2099-105. [15554680 ]
  • Herrick AL, Moore MR, Thompson GG, Ford GP, McColl KE: Cholelithiasis in patients with variegate porphyria. J Hepatol. 1991 Jan;12(1):50-3. [2007776 ]
  • Krijt J, Stranska P, Maruna P, Vokurka M, Sanitrak J: Herbicide-induced experimental variegate porphyria in mice: tissue porphyrinogen accumulation and response to porphyrogenic drugs. Can J Physiol Pharmacol. 1997 Oct-Nov;75(10-11):1181-7. [9431441 ]
  • Bloomer JR: Enzyme defects in the porphyrias and their relevance to the biochemical abnormalities in these disorders. J Invest Dermatol. 1981 Jul;77(1):102-6. [7252240 ]
  • de Villiers JN, Kotze MJ, van Heerden CJ, Sadie A, Gardner HF, Liebenberg J, van Zyl R, du Plessis L, Kimberg M, Frank J, Warnich L: Overrepresentation of the founder PPOX gene mutation R59W in a South African patient with severe clinical manifestation of porphyria. Exp Dermatol. 2005 Jan;14(1):50-5. [15660919 ]
  • Corrigall AV, Hift RJ, Adams PA, Kirsch RE: Inhibition of mammalian protoporphyrinogen oxidase by acifluorfen. Biochem Mol Biol Int. 1994 Dec;34(6):1283-9. [7697001 ]
  • Cox TM, Jack N, Lofthouse S, Watling J, Haines J, Warren MJ: King George III and porphyria: an elemental hypothesis and investigation. Lancet. 2005 Jul 23-29;366(9482):332-5. [16039338 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS7412-77-3
ChEBI57307
ChemSpider20171538
HMDBHMDB01097
IAF126036764
KEGGC01079
MetaboLightsMTBLC57307
PubChem20849104