CHEBI:15430 - protoporphyrin

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ChEBI Name protoporphyrin
ChEBI ID CHEBI:15430
Definition A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:14961, CHEBI:14959, CHEBI:14960, CHEBI:26358, CHEBI:8592
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Formula C34H34N4O4
Net Charge 0
Average Mass 562.65832
Monoisotopic Mass 562.258
InChI 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-
InChIKey KSFOVUSSGSKXFI-UJJXFSCMSA-N
SMILES Cc1c(CCC(O)=O)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(C)c5C=C)c(C)c4C=C)c(C)c3CCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
(via porphyrins )
Application(s): photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
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ChEBI Ontology
Outgoing protoporphyrin (CHEBI:15430) has role Escherichia coli metabolite (CHEBI:76971)
protoporphyrin (CHEBI:15430) has role metabolite (CHEBI:25212)
protoporphyrin (CHEBI:15430) has role mouse metabolite (CHEBI:75771)
protoporphyrin (CHEBI:15430) has role photosensitizing agent (CHEBI:47868)
protoporphyrin (CHEBI:15430) is a protoporphyrins (CHEBI:26361)
protoporphyrin (CHEBI:15430) is conjugate acid of protoporphyrin(2−) (CHEBI:57306)
protoporphyrin (CHEBI:15430) is conjugate acid of protoporphyrinate (CHEBI:36159)
Incoming hematoporphyrin (CHEBI:36162) has functional parent protoporphyrin (CHEBI:15430)
protoporphyrin monomethyl ester (CHEBI:36160) has functional parent protoporphyrin (CHEBI:15430)
protoporphyrin(2−) (CHEBI:57306) is conjugate base of protoporphyrin (CHEBI:15430)
protoporphyrinate (CHEBI:36159) is conjugate base of protoporphyrin (CHEBI:15430)
IUPAC Name
7,12-diethenyl-3,8,13,17-tetramethylporphyrin-2,18-dipropanoic acid
Synonyms Sources
3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid HMDB
3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid IUPAC
H2ppIX IUPAC
Kammerer's prophyrin NIST Chemistry WebBook
ooporphyrin ChemIDplus
Porphyrinogen IX KEGG COMPOUND
Protoporphyrin KEGG COMPOUND
Protoporphyrin IX KEGG COMPOUND
PROTOPORPHYRIN IX PDBeChem
Database Links Databases
3500 DrugCentral
C00007370 KNApSAcK
C02191 KEGG COMPOUND
DB02285 DrugBank
HMDB0000241 HMDB
PP9 PDBeChem
Protoporphyrin_IX Wikipedia
PROTOPORPHYRIN_IX MetaCyc
View more database links
Registry Numbers Types Sources
251232 Gmelin Registry Number Gmelin
380795 Reaxys Registry Number Reaxys
553-12-8 CAS Registry Number KEGG COMPOUND
553-12-8 CAS Registry Number ChemIDplus
553-12-8 CAS Registry Number NIST Chemistry WebBook
635160 Beilstein Registry Number Beilstein
635161 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
18625294 PubMed citation Europe PMC
19005892 PubMed citation Europe PMC
20961864 PubMed citation Europe PMC
21146529 PubMed citation Europe PMC
21167148 PubMed citation Europe PMC
21668870 PubMed citation Europe PMC
21760730 PubMed citation Europe PMC
21913427 PubMed citation Europe PMC
23533060 PubMed citation Europe PMC
Last Modified
22 February 2017