Hydroxypropionic porphyrin III (CHEM034948)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:21:33 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034948
Identification
Common NameHydroxypropionic porphyrin III
ClassSmall Molecule
DescriptionHydroxypropionic porphyrin III is a porphyrin isolated only in patients with porphyria cutanea tarda. Porphyria cutanea tarda (PCT) is a metabolic disorder of haeme biosynthesis caused by decreased activity of uroporphyrinogen decarboxylase. Porphyria cutanea tarda is manifest by fragility, erosions, bullae, milia and scars on sun-exposed skin. Excess porphyrins in the skin interact with light of approximately 400 nm-wavelength radiant energy, forming reactive oxygen species. Porphyria cutanea tarda is categorized as familial, acquired or toxic. Factors that may induce clinical expression of PCT in susceptible individuals include alcohol, oestrogen, iron, polyhalogenated compounds and viral infections. Porphyria cutanea tarda is associated with an increased incidence of the haemochromatosis gene. Treatments for PCT include withdrawal of aggravating factors, phlebotomy and oral antimalarial medications. Porphyria cutanea tarda is associated with hepatic iron overload and responds to iron-reduction therapy. Porphyria cutanea tarda is the most common porphyria, followed by acute intermittent porphyria and erythropoietic protoporphyria. The molecular genetics of the porphyrias is very heterogenous. (PMID: 16315139, 7655298, 11105361) [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
b-Hydroxypropionic acid heptacarboxylic porphyrin IIIHMDB
beta-Hydroxypropionic acid heptacarboxylic porphyrin IIIHMDB
3-[10,15,20-Tris(2-carboxyethyl)-9,14,19-tris(carboxymethyl)-5-methyl-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 FormulaC39H38N4O14
Average Molecular Mass786.737 g/mol
Monoisotopic Mass786.238 g/mol
CAS Registry Number163894-03-9
IUPAC Name3-[10,14,19-tris(2-carboxyethyl)-5,15,20-tris(carboxymethyl)-9-methyl-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-[10,14,19-tris(2-carboxyethyl)-5,15,20-tris(carboxymethyl)-9-methyl-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(CCC(O)=O)C2=N\C\1=C/C1=C(CC(O)=O)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N/C(=C\2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1CC(O)=O
InChI IdentifierInChI=1S/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-27-20(4-8-35(48)49)23(11-38(54)55)31(42-27)16-29-21(5-9-36(50)51)24(12-39(56)57)32(43-29)15-28-19(3-7-34(46)47)22(10-37(52)53)30(41-28)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-14-,28-15-,29-16-,30-13-,31-16-,32-15-
InChI KeyNGHBDJAOMFYFRP-PKXAPQLQSA-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 Solubility0.038 g/LALOGPS
logP1.17ALOGPS
logP2.86ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)5.13ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area318.46 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity195.06 m³·mol⁻¹ChemAxon
Polarizability82.57 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 (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_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-106r-0000000900-5f02404e27194e023728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-0000002900-94a42c1c3c8c4e60e68aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053s-0000009700-f3fa74f52ac07a4406b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xu-0000001900-17c885756ed1506e3c8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000002900-0b78b8f94f9aa3aaa643Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-2000000900-75b8d21b974b1fdd0063Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dj-0000005900-5158682a2327ac61a264Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006t-0000009600-376c90cfb6a9ee5df06bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-0000009100-8b961aaf7f2ca7bd4150Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01dj-0000001900-cfa9a0533d6fc45d581bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-0000009500-b44d0a646f4c779ef9efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003s-0000009500-1864e22e59aa72e2d360Spectrum
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 IDHMDB0000728
FooDB IDFDB022206
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5696
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17215996
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. Luo, Jinli; Lim, Chang Kee. Isolation and characterization of new porphyrin metabolites in human porphyria cutanea tarda and in rats treated with hexachlorobenzene by HPTLC, HPLC and liquid secondary ion mass spectrometry. Biomedical Chromatography (1995), 9(3), 113-22.
2. Luo J, Lim CK: Isolation and characterization of new porphyrin metabolites in human porphyria cutanea tarda and in rats treated with hexachlorobenzene by HPTLC, HPLC and liquid secondary ion mass spectrometry. Biomed Chromatogr. 1995 May-Jun;9(3):113-22.
3. Hoffmann GF, Seppel CK, Holmes B, Mitchell L, Christen HJ, Hanefeld F, Rating D, Nyhan WL: Quantitative organic acid analysis in cerebrospinal fluid and plasma: reference values in a pediatric population. J Chromatogr. 1993 Jul 23;617(1):1-10.
4. Alla V, Bonkovsky HL: Iron in nonhemochromatotic liver disorders. Semin Liver Dis. 2005 Nov;25(4):461-72.
5. Bleasel NR, Varigos GA: Porphyria cutanea tarda. Australas J Dermatol. 2000 Nov;41(4):197-206; quiz 207-8.