Deuteroporphyrin IX (CHEM034911)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:19:29 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034911
Identification
Common NameDeuteroporphyrin IX
ClassSmall Molecule
DescriptionDeuteroporphyrin IX is a non-natural dicarboxylic porphyrin. Deuteroporphyrins are porphyrins with four methyl and two propionic acid side chains attached to the pyrrole rings. Deuteroporphyrin IX is described as a fecal porphyrin in patients with endemic chronic arsenic poisoning. (Environmental Sciences (Tokyo, Japan) (2001), 8(6), 561-570.) Excess accumulation of the biosynthetic intermediate protoporphyrin can lead to extensive tissue damage upon exposure to light since protoporpyhyrin is a potent photosensitizing agent, giving rise to membrane-destroying oxygen radicals or singlet oxygen. For instance, in the human porphyria disease porphyria variegata, a genetic deficiency in a heme biosynthetic enzyme, protoporphyrinogen oxidase, leads to protoporphyrin accumulation and lightdependent skin photosensitivity. Horseradish peroxidase (HRP) in the presence of glutathione (GSH) could oxidize the non-natural porphyrin deuteroporphyrin IX, which is closely related to protoporphyrin IX. The product is a unique green chlorin. One of the pyrrole rings had been modified by addition of an hydroxy and an oxo group, thus giving the characteristic reduced pyrrole ring of the chlorine. Of most importance for human medicine, peroxidative enzymes present in mammalian cells can also carry out these GSH-dependent oxidative conversions of protoporphyrin and deuteroporphyrin. (PMID: 10334939) [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DeuteroporphyrinHMDB
Deuteroporphyrin-IXHMDB
3-[20-(2-Carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoateHMDB
Chemical FormulaC30H30N4O4
Average Molecular Mass510.584 g/mol
Monoisotopic Mass510.227 g/mol
CAS Registry Number448-65-7
IUPAC Name3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid
Traditional Name3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid
SMILESCC1=C/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(C=C4C)\C=C\1/N\2)/C(CCC(O)=O)=C3C
InChI IdentifierInChI=1S/C30H30N4O4/c1-15-9-20-12-25-17(3)21(5-7-29(35)36)27(33-25)14-28-22(6-8-30(37)38)18(4)26(34-28)13-24-16(2)10-19(32-24)11-23(15)31-20/h9-14,31,34H,5-8H2,1-4H3,(H,35,36)(H,37,38)/b19-11-,20-12-,23-11-,24-13-,25-12-,26-13-,27-14-,28-14-
InChI KeyKWKUIRGQJJFUCG-LMKUSPAJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassPorphyrins
Direct ParentPorphyrins
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP3.55ALOGPS
logP5.04ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)5.13ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area131.96 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity144.44 m³·mol⁻¹ChemAxon
Polarizability58.99 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-1000900000-15951e538043265399fdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9000042000-2e895757cfdc0e825c15Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000910000-f5c44644fab1645d66f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-0000900000-136b41a450da97bcb044Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2004900000-95ebfc8b06d0954336d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000790000-28a26fd2cee9c5f5bce2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mo-1000920000-40c562bc10ec54dd93eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000400000-ff5b245c3124eac15479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0000940000-9c5d75f11faaf2cfb824Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-0000910000-428f4d355cd73ae14f5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-1002900000-988c757c29363d75efadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000490000-c0cc83047c1ea74df080Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aos-0000930000-4676f92ea6a756fa34a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0001900000-41b81f68c2b9448b0e25Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000579
FooDB IDFDB022126
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5561
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID16736707
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Borovkov, V. V.; Filippovich, E. I.; Evstigneeva, R. P. Synthesis and spectral investigation of deuteroporphyrin IX-based porphyrinquinone derivatives. Khimiya Geterotsiklicheskikh Soedinenii (1988), (5), 608-16.
2. Rose IS, Young GP, St John DJ, Deacon MC, Blake D, Henderson RW: Effect of ingestion of hemoproteins on fecal excretion of hemes and porphyrins. Clin Chem. 1989 Dec;35(12):2290-6.
3. Rotenberg M, Margalit R: Deuteroporphyrin-albumin binding equilibrium. The effects of porphyrin self-aggregation studied for the human and the bovine proteins. Biochem J. 1985 Jul 1;229(1):197-203.
4. Severina IS, Pyatakova NV, Shchegolev AY, Ponomarev GV: YC-1-like potentiation of NO-dependent activation of soluble guanylate cyclase by derivatives of protoporphyrin IX. Biochemistry (Mosc). 2006 Mar;71(3):340-4.
5. Morita I, Kawamoto M, Hattori M, Eguchi K, Sekiba K, Yoshida H: Determination of tryptophan and its metabolites in human plasma and serum by high-performance liquid chromatography with automated sample clean-up system. J Chromatogr. 1990 Apr 6;526(2):367-74.
6. Cohen S, Margalit R: Binding of porphyrin to human serum albumin. Structure-activity relationships. Biochem J. 1990 Sep 1;270(2):325-30.
7. Jacobs NJ, Kruszyna HG, Hier JS, Dayan FE, Duke SO, Pont F, Montforts FP: Glutathione-dependent oxidative modification of protoporphyrin and other dicarboxylic porphyrins by mammalian and plant peroxidases. Biochem Biophys Res Commun. 1999 May 27;259(1):195-200.