CHEBI:50385 - hemin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name hemin
ChEBI ID CHEBI:50385
Definition It is used as a prescription medication to relieve repeated attacks of acute intermittent porphyria related to the menstrual cycle in affected women.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:5655, CHEBI:24493
Supplier Information ChemicalBook:CB2684343, eMolecules:509516, ZINC000000085378
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Folate, also known as vitamin B9 and folacin, is one of the B vitamins. Manufactured folic acid, which is converted into folate by the body, is used as a dietary supplement and in food fortification as it is more stable during processing and storage. Folate is required for the body to make DNA and RNA and metabolise amino acids necessary for cell division and maturation of blood cells. As the human body cannot make folate, it is required in the diet, making it an essential nutrient. It occurs naturally in many foods. The recommended adult daily intake of folate in the U.S. is 400 micrograms from foods or dietary supplements. Folate in the form of folic acid is used to treat anemia caused by folate deficiency. Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in the baby. NTDs include anencephaly and spina bifida, among other defects. Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs. More than 80 countries use either mandatory or voluntary fortification of certain foods with folic acid as a measure to decrease the rate of NTDs. Long-term supplementation with relatively large amounts of folic acid is associated with a small reduction in the risk of stroke and an increased risk of prostate cancer. There are concerns that large amounts of supplemental folic acid can hide vitamin B12 deficiency. Not consuming enough folate can lead to folate deficiency. This may result in a type of anemia in which red blood cells become abnormally large. Symptoms may include feeling tired, heart palpitations, shortness of breath, open sores on the tongue, and changes in the color of the skin or hair. Folate deficiency in children may develop within a month of poor dietary intake. In adults, normal total body folate is between 10 and 30 mg with about half of this amount stored in the liver and the remainder in blood and body tissues. In plasma, the natural folate range is 150 to 450 nM. Folate was discovered between 1931 and 1943. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 65th most commonly prescribed medication in the United States, with more than 10 million prescriptions. The term "folic" is from the Latin word folium (which means leaf) because it was found in dark-green leafy vegetables.
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Formula C34H32ClFeN4O4
Net Charge 0
Average Mass 651.94014
Monoisotopic Mass 651.14614
InChI InChI=1S/C34H34N4O4.ClH.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);1H;/q;;+3/p-3/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;
InChIKey BTIJJDXEELBZFS-HXFTUNQESA-K
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(Cl)(n14)n1c(=C6)c(C)c(CCC(O)=O)c1=C2
Roles Classification
Biological Role(s): autophagy inducer
Any compound that induces the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell).
ferroptosis inducer
Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
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 hemin (CHEBI:50385) has role autophagy inducer (CHEBI:138880)
hemin (CHEBI:50385) has role ferroptosis inducer (CHEBI:173085)
hemin (CHEBI:50385) is a heme b (CHEBI:26355)
IUPAC Name
chlorido(protoporphyrinato)iron(III)
Synonyms Sources
chloro(protoporphyrinato)iron(III) JCBN
chloro[3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2−)]iron(III) IUPAC
chlorohemin ChemIDplus
chloroprotoferrihem ChemIDplus
ferriprotoporphyrin IX chloride ChEBI
Hämin ChEBI
hemin ChemIDplus
Hemin KEGG COMPOUND
hemin chloride ChEBI
hemin IX ChemIDplus
Hemine KEGG COMPOUND
hémine IUPAC
protohemin JCBN
protohemin IX ChemIDplus
Brand Name Source
Panhematin DrugBank
Manual Xrefs Databases
C06767 KEGG COMPOUND
CPD-11678 MetaCyc
DB03404 DrugBank
FDB005746 FooDB
Hemin Wikipedia
HMDB0000887 HMDB
View more database links
Registry Numbers Types Sources
1236156 Beilstein Registry Number Beilstein
16009-13-5 CAS Registry Number ChemIDplus
2373175 Gmelin Registry Number Gmelin
4648025 Beilstein Registry Number Beilstein
5717757 Beilstein Registry Number Beilstein
953895 Beilstein Registry Number Beilstein
Citations Types Sources
30523204 PubMed citation Europe PMC
31102787 PubMed citation Europe PMC
33603380 PubMed citation Europe PMC
33624637 PubMed citation Europe PMC
33761605 PubMed citation Europe PMC
33987332 PubMed citation Europe PMC
Last Modified
11 June 2021