CHEBI:26355 - heme b

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ChEBI Name heme b
ChEBI ID CHEBI:26355
ChEBI ASCII Name heme b
Definition A metalloprotoporphyrin in which the four pyrrole nitrogens of the protoporphyrin moiety are coordinated to iron. It is the most abundant of the heme compounds.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
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S-Adenosyl methionine (SAM), also known under the commercial names of SAMe, SAM-e, or AdoMet, is a common cosubstrate involved in methyl group transfers, transsulfuration, and aminopropylation. Although these anabolic reactions occur throughout the body, most SAM is produced and consumed in the liver. More than 40 methyl transfers from SAM are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase. SAM was first discovered by Giulio Cantoni in 1952. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. In eukaryotic cells, SAM serves as a regulator of a variety of processes including DNA, tRNA, and rRNA methylation; immune response; amino acid metabolism; transsulfuration; and more. In plants, SAM is crucial to the biosynthesis of ethylene, an important plant hormone and signaling molecule.
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Formula C34H32FeN4O4
Net Charge 0
Average Mass 616.48700
Monoisotopic Mass 616.17729
InChI InChI=1S/C34H34N4O4.Fe/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;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
InChIKey KABFMIBPWCXCRK-RGGAHWMASA-L
SMILES CC1=C(CCC(O)=O)C2=[N]3C1=Cc1c(C)c(C=C)c4C=C5C(C)=C(C=C)C6=[N]5[Fe]3(n14)n1c(=C6)c(C)c(CCC(O)=O)c1=C2
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via heme )
prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
(via heme )
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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing heme b (CHEBI:26355) is a heme (CHEBI:30413)
heme b (CHEBI:26355) is a metalloprotoporphyrin (CHEBI:36158)
Incoming ferriheme b (CHEBI:36144) is a heme b (CHEBI:26355)
ferriheme b(1−) (CHEBI:55376) is a heme b (CHEBI:26355)
ferroheme b (CHEBI:17627) is a heme b (CHEBI:26355)
hematin (CHEBI:36161) is a heme b (CHEBI:26355)
hemin (CHEBI:50385) is a heme b (CHEBI:26355)
IUPAC Name
(protoporphyrinato)iron
Synonyms Sources
(7,12-diethenyl-3,8,13,17-tetramethylporphyrin-2,18-dipropanoato)iron IUPAC
[3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2−)]iron IUPAC
Haem KEGG COMPOUND
haem b COMe
heme ChEBI
Heme B KEGG COMPOUND
heme b IUPAC
Protoheme KEGG COMPOUND
protoheme ChEBI
Protoheme IX KEGG COMPOUND
PROTOPORPHYRIN IX CONTAINING FE PDBeChem
Manual Xrefs Databases
3KS0 PDB
C00032 KEGG COMPOUND
ECMDB03178 ECMDB
HEM PDBeChem
Heme_B Wikipedia
MOL000013 COMe
View more database links
Registry Number Type Source
14875-96-8 CAS Registry Number KEGG COMPOUND
Citations Types Sources
20546754 PubMed citation Europe PMC
29286160 PubMed citation Europe PMC
Last Modified
09 February 2018