131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester (PAMDB120283)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120283
Identification
Name: 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester
Description:The conjugate base of magnesium 131-hydroxyprotoporphyrin 13-monomethyl ester, formed by deprotonation of the carboxyethyl group at C-17. It is the principal species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • magnesium 131-hydroxyprotoporphyrinate 13-monomethyl ester
  • Mg-131-hydroxyprotoporphyrin 13-monomethyl ester
Chemical Formula: C35H33N4O5MG
Average Molecular Weight: 613.974
Monoisotopic Molecular Weight: 614.238
InChI Key: MVCDIAGKFJFPBB-JXBSUKTBSA-L
InChI:InChI=1S/C35H35N4O5.Mg/c1-8-21-17(3)24-12-25-19(5)23(10-11-33(41)42)30(38-25)15-31-35(32(40)16-34(43)44-7)20(6)27(39-31)14-29-22(9-2)18(4)26(37-29)13-28(21)36-24;/h8-9,12-15,32,40H,1-2,10-11,16H2,3-7H3,(H2-,36,37,38,39,41,42);/q-1;+2/p-2/b24-12-,25-12-,26-13-,27-14-,28-13-,29-14-,30-15-,31-15-;
CAS number: 493-90-3
IUPAC Name:3-[20-(2-carboxyethyl)-10,15-diethyl-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1?,??1????.1??,???tetracosa-1,3(24),4,6,8,10,12,14,16,18(21),19-undecaen-4-yl]propanoic acid
Traditional IUPAC Name: MPIX
SMILES:C=CC1(C5(N6(C(C=1C)=CC2(C(=C(C(N=2)=CC3(N(C(=C(C=3C(CC(OC)=O)O)C)C=C4(C(=C(C(=N4)C=5)C)C=C))[Mg]6))CCC(=O)[O-])C))))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as metalloporphyrins. These are polycyclic compounds containing a porphyrin moiety and a metal atom.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Tetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct Parent Metalloporphyrins
Alternative Parents
Substituents
  • Metalloporphyrin
  • Porphyrin
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Hydroxy acid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Methyl ester
  • Pyrrole
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organic salt
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
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 Solubility0.024 mg/mLALOGPS
logP4.82ALOGPS
logP7.29ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area131.96 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity163.72 m3·mol-1ChemAxon
Polarizability67.28 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
magnesium-protoporphyrin IX 13-monomethyl ester + Water + NADP+ → 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + Hydrogen ion
131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ → 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + Hydrogen ion
magnesium-protoporphyrin IX 13-monomethyl ester + Oxygen + NADPH + Hydrogen ion → 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + Water
131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + Hydrogen ion + Oxygen → 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + Water
Pathways:
  • chlorophyllide a biosynthesis III (aerobic, light independent)PWY-7159
  • chlorophyllide a biosynthesis I (aerobic, light-dependent)CHLOROPHYLL-SYN
  • chlorophyllide a biosynthesis II (anaerobic)PWY-5531
    Spectra
    Spectra: Not Available
    References
    References:
    • Tiribelli C, Ostrow JD: New concepts in bilirubin and jaundice: report of the Third International Bilirubin Workshop, April 6-8, 1995, Trieste, Italy. Hepatology. 1996 Nov;24(5):1296-311. [8903413 ]
    • Vreman HJ, Ekstrand BC, Stevenson DK: Selection of metalloporphyrin heme oxygenase inhibitors based on potency and photoreactivity. Pediatr Res. 1993 Feb;33(2):195-200. [8433895 ]
    • Greenbaum NL, Kappas A: Comparative photoactivity of tin and zinc porphyrin inhibitors of heme oxygenase: pronounced photolability of the zinc compounds. Photochem Photobiol. 1991 Aug;54(2):183-92. [1780355 ]
    • Drummond GS, Greenbaum NL, Kappas A: Tin(Sn+4)-diiododeuteroporphyrin; an in vitro and in vivo inhibitor of heme oxygenase with substantially reduced photoactive properties. J Pharmacol Exp Ther. 1991 Jun;257(3):1109-13. [2046022 ]
    • Beukeveld GJ, Meerman L, Huizenga JR, Venekamp-Hoolsema EE, Gips CH, Wolthers BG: Determination of porphyrins in bile using high performance liquid chromatography and some clinical applications. Eur J Clin Chem Clin Biochem. 1994 Mar;32(3):153-9. [8031966 ]
    • Beukeveld GJ, Bijleveld CM, Kuipers F, Kreeftenberg HG, Huizenga JR, te Velde K, Wolthers BG: Evaluation and clinical application of the Enterotest for the determination of human biliary porphyrin composition. Eur J Clin Chem Clin Biochem. 1995 Jul;33(7):453-62. [7548456 ]
    • Galbraith RA, Kappas A: Pharmacokinetics of tin-mesoporphyrin in man and the effects of tin-chelated porphyrins on hyperexcretion of heme pathway precursors in patients with acute inducible porphyria. Hepatology. 1989 Jun;9(6):882-8. [2714739 ]
    • Takaoka Y, Matsuura S, Boda K, Nagai H: The effect of mesoporphyrin on the production of cytokines by inflammatory cells in vitro. Jpn J Pharmacol. 1999 May;80(1):33-40. [10446754 ]
    Synthesis Reference: Fabry, T. L.; Simo, C.; Javaherian, K. Preparation of mesoporphyrin IX and copper and manganese mesoporphyrin complexes of apohemoglobin. Biochimica et Biophysica Acta, Protein Structure (1968), 160(1), 118-22.
    Material Safety Data Sheet (MSDS) Download (PDF)
    External Links:
    ResourceLink
    HMDBHMDB02379
    CHEBI60489
    PUBCHEM44229246
    LIGAND-CPDC11829