ContaminantDB: Protoporphyrin IX

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:17 UTC

Update Date

2026-05-14 17:33:28 UTC

Accession Number

CHEM003400

Identification

Common Name

Protoporphyrin IX

Class

Small Molecule

Description

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 accumulated 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.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Animal Toxin
Drug
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid	ChEBI
3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid	ChEBI
H2PpIX	ChEBI
Kammerer's prophyrin	ChEBI
Ooporphyrin	ChEBI
Porphyrinogen IX	ChEBI
3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionate	Generator
3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoate	Generator
3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di	HMDB
PpIX	HMDB
Protoporphyrin	HMDB
Protoporphyrin-"ix"	HMDB
Protoporphyrin-IX	HMDB

Chemical Formula

C₃₄H₃₄N₄O₄

Average Molecular Mass

562.658 g/mol

Monoisotopic Mass

562.258 g/mol

CAS Registry Number

553-12-8

IUPAC Name

3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid

Traditional Name

3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid

SMILES

CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O

InChI Identifier

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-

InChI Key

KSFOVUSSGSKXFI-UJJXFSCMSA-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Porphyrins

Direct Parent

Porphyrins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Membrane
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Adrenal Medulla
Bladder
Erythrocyte
Fibroblasts
Gastrointestinal Tract
Intestine
Kidney
Liver
Lymphocyte
Platelet
Skin
Spleen
Stratum Corneum
T-Lymphocyte
Testes
Thyroid Gland
Urinary Bladder

Pathways

Name	SMPDB Link	KEGG Link
Porphyrin Metabolism	SMP00024	map00860
Porphyria Variegata (PV)	SMP00346	Not Available

Applications

photosensitizing agent

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	300°C
Boiling Point	Not Available
Solubility	0.169 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	4.4	ALOGPS
logP	6.78	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	4.96	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	131.96 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	163.81 m³·mol⁻¹	ChemAxon
Polarizability	66.03 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxu-1000290000-e22236fe3cca8eed1ecf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6000094000-b9c12952e100c5144cab	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Protoporphyrin IX,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000090000-5d5be53410134c5719ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-1000590000-2d4157b9f73534d95a9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-1000910000-07524a9291a1921dfafc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000090000-5df26c1cfb9a0b16a91a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0296-1000190000-2d4bcb49201fc10adc09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000230000-064fb944a966d08c06bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000090000-87c1740ecd1a28f4a2d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xu-0000590000-99160b987bb7e62ab362	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0000900000-f2d9118441a9c8c47d79	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-0000090000-d428ac6dc2fc4794cc41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0j4j-0000090000-2b065966ec57bb97d511	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-1000970000-b435817e4dc349e65ab3	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of porophyrins are associated with porphyrias such as Porphyria variegate, Acute Intermittent Porphyria and Hereditary Coproporphyria (HCP).

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB02285

HMDB ID

HMDB0000241

FooDB ID

FDB004277

Phenol Explorer ID

Not Available

KNApSAcK ID

C00007370

BiGG ID

Not Available

BioCyc ID

PROTOPORPHYRIN_IX

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Protoporphyrin_IX

Chemspider ID

10469486

ChEBI ID

15430

PubChem Compound ID

Not Available

Kegg Compound ID

C02191

YMDB ID

YMDB00055

ECMDB ID

ECMDB00241

References

Synthesis Reference

Elaine A. Best, Charles Lee Hershberger, Christopher Carl Frye, “Methods of reducing the levels of protoporphyrin IX in recombinant hemoglobin preparations.” U.S. Patent US6136565, issued April, 1998.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18625294

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19005892

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20961864

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21146529

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21167148

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21668870

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21760730

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21913427

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23533060

Protoporphyrin IX (CHEM003400)

Structure for CHEM003400: Protoporphyrin IX