Protoporphyrin IX
Protoporphyrins are tetrapyrroles containing 4 methyl, 2 propionic and 2 vinyl side chains. Protopophyrin is produced by oxidation of the methylene bridge of protoporphyrinogen. Protoporphyrin IX is the only naturally occurring isomer; it is an intermediate in heme biosynthesis, combining with ferrous iron to form protoheme IX, the heme prosthetic group of hemoglobin. Protoporphyrin IX is created by the enzyme protoporphyrinogen oxidase. The enzyme ferrochelatase converts it into heme. Protoporphyrin IX naturally occurs in small amounts in feces. It is accumliated and excreted excessively in the feces in protoporphyria and variegate porphyria. Protoporphyrin IX is also responsible for the brown pigment (Ooporphyrin) of birds eggs Protoporphyrin IX is used as a branch point in the biosynthetic pathway leading to Heme (by insertion of iron) and chlorophylls (by insertion of Mg and further side-chain transformation). Protoporphyrin IX can be used to treat liver disorders, mainly as the sodium salt. Shows anti-HIV activity.
MOLSDFPDBSMILESInChI
Structure for HMDB00241 (Protoporphyrin IX)
C34H34N4O4
562.6582
562.258005596
3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid
protoporphyrin
553-12-8
CC1=C(CCC(O)=O)/C2=C/C3=N/C(=CC4=C(C)C(C=C)=C(N4)/C=C4N=C(C=C1/N2)C(C=C)=C4C)/C(C)=C3CCC(O)=O
InChI=1S/C34H34N4O4/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/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-
KSFOVUSSGSKXFI-UJJXFSCMSA-N
Not classified
Detected and Quantified
Not Available
Solid
Not Available
Not Available
None
None
DB02285
Not Available
Not Available
Not Available
FDB004277
C00007370
10469486
C02191
PROTOPORPHYRIN_IX
39293
Protoporphyrin IX
HMDB00241
HMDB00241
4158
Not Available
1HBG
15430
Product: Saroglitazar (Magnesium)
- Messmann H, Knuchel R, Baumler W, Holstege A, Scholmerich J: Endoscopic fluorescence detection of dysplasia in patients with Barretts esophagus, ulcerative colitis, or adenomatous polyps after 5-aminolevulinic acid-induced protoporphyrin IX sensitization. Gastrointest Endosc. 1999 Jan;49(1):97-101. [PubMed:9869731 ]
- Stankiewicz A, Lutz W, Krajewska B, Szulc B: [Plasma indicators of iron metabolism in persons occupationally exposed to organic solvents with normal and increased levels of protoporphyrin IX in erythrocytes]. Pol Tyg Lek. 1986 Jul 7;41(27):851-4. [PubMed:3763462 ]
- Stankiewicz A: [Erythrocyte protoporphyrin IX in occupational exposure to asbestos]. Med Pr. 1984;35(5):351-4. [PubMed:6530952 ]
- Sudworth CD, Stringer MR, Cruse-Sawyer JE, Brown SB: Fluorescence microspectroscopy technique for the study of intracellular protoporphyrin IX dynamics. Appl Spectrosc. 2003 Jun;57(6):682-8. [PubMed:14658702 ]
- Kufner G, Schlegel H, Jager R: A spectrophotometric micromethod for determining erythrocyte protoporphyrin-IX in whole blood or erythrocytes. Clin Chem Lab Med. 2005;43(2):183-91. [PubMed:15843214 ]
- Stankiewicz A: The concentration of protoporphyrin IX in workers occupationally exposed to lead. Mater Med Pol. 1989 Apr-Jun;21(2):100-2. [PubMed:2488459 ]
- Krieg RC, Fickweiler S, Wolfbeis OS, Knuechel R: Cell-type specific protoporphyrin IX metabolism in human bladder cancer in vitro. Photochem Photobiol. 2000 Aug;72(2):226-33. [PubMed:10946577 ]
- Bailey GG, Needham LL: Simultaneous quantification of erythrocyte zinc protoporphyrin and protoporphyrin IX by liquid chromatography. Clin Chem. 1986 Dec;32(12):2137-42. [PubMed:3779978 ]
- Chisolm J Jr, Brown DH: Micro-scale photofluorometric determination of “free erythrocyte pophyrin” (protoporphyrin IX). Clin Chem. 1975 Oct;21(11):1669-82. [PubMed:1164799 ]
- Casas A, Batlle AM, Butler AR, Robertson D, Brown EH, MacRobert A, Riley PA: Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. Br J Cancer. 1999 Jul;80(10):1525-32. [PubMed:10408393 ]
- Smits T, Robles CA, van Erp PE, van de Kerkhof PC, Gerritsen MJ: Correlation between macroscopic fluorescence and protoporphyrin IX content in psoriasis and actinic keratosis following application of aminolevulinic acid. J Invest Dermatol. 2005 Oct;125(4):833-9. [PubMed:16185285 ]
- Bartosova J, Hrkal Z: Accumulation of protoporphyrin-IX (PpIX) in leukemic cell lines following induction by 5-aminolevulinic acid (ALA). Comp Biochem Physiol C Toxicol Pharmacol. 2000 Jul;126(3):245-52. [PubMed:11048674 ]
- Sakai T, Takeuchi Y, Ikeya Y, Araki T, Ushio K: [Automated HPLC method for determining zinc protoporphyrin IX and protoporphyrin IX in erythrocytes of workers exposed to lead]. Sangyo Igaku. 1988 Nov;30(6):467-74. [PubMed:3221502 ]
- Stankiewicz A, Lutz W, Szeszko A: [Protoporphyrin IX level in erythrocytes of persons with alcoholic liver cirrhosis]. Pol Tyg Lek. 1985 Jul 15;40(28):787-9. [PubMed:4059100 ]
- Star WM, Aalders MC, Sac A, Sterenborg HJ: Quantitative model calculation of the time-dependent protoporphyrin IX concentration in normal human epidermis after delivery of ALA by passive topical application or lontophoresis. Photochem Photobiol. 2002 Apr;75(4):424-32. [PubMed:12003134 ]
- von Beckerath M, Juzenas P, Ma LW, Iani V, Lofgren L, Moan J: The influence of UV exposure on 5-aminolevulinic acid-induced protoporphyrin IX production in skin. Photochem Photobiol. 2001 Dec;74(6):825-8. [PubMed:11783939 ]
- Gottsch JD, Graham CR Jr, Hairston RJ, Chen CH, Green WR, Stark WJ: Protoporphyrin IX photosensitization of corneal endothelium. Arch Ophthalmol. 1989 Oct;107(10):1497-500. [PubMed:2803100 ]
- Bissonnette R, Zeng H, McLean DI, Korbelik M, Lui H: Oral aminolevulinic acid induces protoporphyrin IX fluorescence in psoriatic plaques and peripheral blood cells. Photochem Photobiol. 2001 Aug;74(2):339-45. [PubMed:11547574 ]
- Rick K, Sroka R, Stepp H, Kriegmair M, Huber RM, Jacob K, Baumgartner R: Pharmacokinetics of 5-aminolevulinic acid-induced protoporphyrin IX in skin and blood. J Photochem Photobiol B. 1997 Oct;40(3):313-9. [PubMed:9372622 ]
- De Rosa FS, Marchetti JM, Thomazini JA, Tedesco AC, Bentley MV: A vehicle for photodynamic therapy of skin cancer: influence of dimethylsulphoxide on 5-aminolevulinic acid in vitro cutaneous permeation and in vivo protoporphyrin IX accumulation determined by confocal microscopy. J Control Release. 2000 Apr 3;65(3):359-66. [PubMed:10699294 ]
Enzymes
- General function:
- Involved in coproporphyrinogen oxidase activity
- Specific function:
- Key enzyme in heme biosynthesis. Catalyzes the oxidative decarboxylation of propionic acid side chains of rings A and B of coproporphyrinogen III.
- Gene Name:
- CPOX
- Uniprot ID:
- P36551
- Molecular weight:
- 50151.605
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX.
- Gene Name:
- PPOX
- Uniprot ID:
- P50336
- Molecular weight:
- 50764.8
Reactions
- General function:
- Involved in ferrochelatase activity
- Specific function:
- Catalyzes the ferrous insertion into protoporphyrin IX.
- Gene Name:
- FECH
- Uniprot ID:
- P22830
- Molecular weight:
- 47861.77
Reactions
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Stores iron in a soluble, non-toxic, readily available form. Important for iron homeostasis. Iron is taken up in the ferrous form and deposited as ferric hydroxides after oxidation. Also plays a role in delivery of iron to cells. Mediates iron uptake in capsule cells of the developing kidney
- Gene Name:
- FTL
- Uniprot ID:
- P02792
- Molecular weight:
- 20019.5
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
- General function:
- Involved in ferrochelatase activity
- Specific function:
- Catalyzes the ferrous insertion into protoporphyrin IX
- Gene Name:
- Not Available
- Uniprot ID:
- Q53FU1
- Molecular weight:
- 47488.3
- General function:
- Involved in ferrochelatase activity
- Specific function:
- Catalyzes the ferrous insertion into protoporphyrin IX
- Gene Name:
- Not Available
- Uniprot ID:
- Q5TZY0
- Molecular weight:
- 47680.5
- General function:
- Involved in ferrochelatase activity
- Specific function:
- Catalyzes the ferrous insertion into protoporphyrin IX
- Gene Name:
- DKFZp686P18130
- Uniprot ID:
- Q7KZA3
- Molecular weight:
- 47131.9