Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C34H32N4O4.Fe |
| Molecular Weight | 616.487 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Fe++].CC1=C(CCC(O)=O)C2=CC3=NC(=CC4=C(C)C(C=C)=C([N-]4)C=C5N=C(C=C1[N-]2)C(C=C)=C5C)C(C)=C3CCC(O)=O
InChI
InChIKey=KABFMIBPWCXCRK-RGGAHWMASA-L
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-;
| Molecular Formula | Fe |
| Molecular Weight | 55.845 |
| Charge | 2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C34H32N4O4 |
| Molecular Weight | 560.6423 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/9057849
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/9057849
Ferroheme is formed when iron is inserted into protoporphyrin IX. The active center of hemoglobin and myoglobin consists of iron Ferroheme complex bound through a single, “proximal”, axial histidine (His) to the protein It is an iron containing cofactor that is involved with a wide range of cellular functions including oxygen transport. The antimalarial activity of a number of artemisinin derivatives, both newly synthesized and currently used as drugs, against Plasmodium falciparum in culture shows a correlation with their affinity of binding with Ferroheme.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Nitration of Y10 in Aβ1-40: is it a compensatory reaction against oxidative/nitrative stress and Aβ aggregation? | 2015-03-16 |
|
| Key roles for tyrosine 10 in aβ-heme complexes and its relevance to oxidative stress. | 2015-03-16 |
|
| Structure of REV-ERBβ ligand-binding domain bound to a porphyrin antagonist. | 2014-07-18 |
|
| Increased HO-1 levels ameliorate fatty liver development through a reduction of heme and recruitment of FGF21. | 2014-03 |
|
| Aβ interacts with both the iron center and the porphyrin ring of heme: mechanism of heme's action on Aβ aggregation and disaggregation. | 2013-02-18 |
|
| Heme and heme biosynthesis intermediates induce heme oxygenase-1 and cytochrome P450 2A5, enzymes with putative sequential roles in heme and bilirubin metabolism: different requirement for transcription factor nuclear factor erythroid- derived 2-like 2. | 2012-11 |
|
| Cadmium-induced apoptosis in the BJAB human B cell line: involvement of PKC/ERK1/2/JNK signaling pathways in HO-1 expression. | 2012-10-28 |
|
| Cytochrome b5 increases cytochrome P450 3A4-mediated activation of anticancer drug ellipticine to 13-hydroxyellipticine whose covalent binding to DNA is elevated by sulfotransferases and N,O-acetyltransferases. | 2012-05-21 |
|
| Concomitant induction of heme oxygenase-1 attenuates the cytotoxicity of arsenic species from lumbricus extract in human liver HepG2 cells. | 2012-04 |
|
| Enhancement of nitrite on heme-induced oxidative reactions: A potential toxicological implication. | 2012-02 |
|
| Lon peptidase 1 (LONP1)-dependent breakdown of mitochondrial 5-aminolevulinic acid synthase protein by heme in human liver cells. | 2011-07-29 |
|
| DiGeorge critical region 8 (DGCR8) is a double-cysteine-ligated heme protein. | 2011-05-13 |
|
| Up-regulation of A1M/α1-microglobulin in skin by heme and reactive oxygen species gives protection from oxidative damage. | 2011 |
|
| The Fowler syndrome-associated protein FLVCR2 is an importer of heme. | 2010-11 |
|
| Pro-healing potential of hemin: an inducer of heme oxygenase-1. | 2010-10-25 |
|
| Protein assay for heme oxygenase-1 (HO-1) induced by chemicals in HepG2 cells. | 2009-12 |
|
| Preparation of a biologically active apo-cytochrome b5 via heterologous expression in Escherichia coli. | 2009-08 |
|
| Role for copper in the cellular and regulatory effects of heme-hemopexin. | 2009-06 |
|
| 15-Deoxy-Delta12,14-prostaglandin J2 upregulates the expression of heme oxygenase-1 and subsequently matrix metalloproteinase-1 in human breast cancer cells: possible roles of iron and ROS. | 2009-04 |
|
| Comparative analysis of gene expression changes mediated by individual constituents of hemozoin. | 2009-03-16 |
|
| Regulation of heme synthesis and proteasomal activity by copper: possible implications for Wilson's disease. | 2009 |
|
| Heme induces endothelial tissue factor expression: potential role in hemostatic activation in patients with hemolytic anemia. | 2008-12 |
|
| Heme oxygenase-1 induction depletes heme and attenuates pulmonary artery relaxation and guanylate cyclase activation by nitric oxide. | 2008-03 |
|
| Rev-erbalpha, a heme sensor that coordinates metabolic and circadian pathways. | 2007-12-14 |
|
| Identification of heme as the ligand for the orphan nuclear receptors REV-ERBalpha and REV-ERBbeta. | 2007-12 |
|
| Functional characterization of human proton-coupled folate transporter/heme carrier protein 1 heterologously expressed in mammalian cells as a folate transporter. | 2007-08 |
|
| Modulation by heme and zinc protoporphyrin of colonic heme oxygenase-1 and experimental inflammatory bowel disease in the rat. | 2007-04-30 |
|
| Motexafin gadolinium-induced cell death correlates with heme oxygenase-1 expression and inhibition of P450 reductase-dependent activities. | 2007-01 |
|
| Haem carrier protein 1 (HCP1): Expression and functional studies in cultured cells. | 2006-12-22 |
|
| Up-regulation of heme oxygenase provides vascular protection in an animal model of diabetes through its antioxidant and antiapoptotic effects. | 2006-12 |
|
| Carbon monoxide contributes to hypotension-induced cerebrovascular vasodilation in piglets. | 2006-11 |
|
| Identification of a mammalian mitochondrial porphyrin transporter. | 2006-10-05 |
|
| Mitochondria in hematopoiesis and hematological diseases. | 2006-08-07 |
|
| The reactions of neuroglobin with CO: evidence for two forms of the ferrous protein. | 2006-08 |
|
| Heme oxygenase-1 enhances renal mitochondrial transport carriers and cytochrome C oxidase activity in experimental diabetes. | 2006-06-09 |
|
| Heme oxygenase-1 protects tumor cells against photodynamic therapy-mediated cytotoxicity. | 2006-06-08 |
|
| Amyloid-beta peptide binds with heme to form a peroxidase: relationship to the cytopathologies of Alzheimer's disease. | 2006-02-28 |
|
| Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. | 2005-12 |
|
| Heme oxygenase-1-generated biliverdin ameliorates experimental murine colitis. | 2005-04 |
|
| Dynamic cytoplasmic anchoring of the transcription factor Bach1 by intracellular hyaluronic acid binding protein IHABP. | 2005-03 |
|
| Heme oxygenase-1-mediated partial cytoprotective effect by NO on cadmium-induced cytotoxicity in C6 rat glioma cells. | 2005-02 |
|
| Differential gene expression in rat colon by dietary heme and calcium. | 2005-01 |
|
| Regulation of expression of the human heme oxygenase-1 gene in transfected chick embryo liver cell cultures. | 1997-06-26 |
|
| Mechanism of induction of heme oxygenase by metalloporphyrins in primary chick embryo liver cells: evidence against a stress-mediated response. | 1997-04 |
|
| The heme-responsive element of the mouse heme oxygenase-1 gene is an extended AP-1 binding site that resembles the recognition sequences for MAF and NF-E2 transcription factors. | 1996-04-25 |
|
| Inhibition of human immunodeficiency virus-1 reverse transcriptase by heme and synthetic heme analogs. | 1996-01 |
|
| Identification of a second region upstream of the mouse heme oxygenase-1 gene that functions as a basal level and inducer-dependent transcription enhancer. | 1995-05-19 |
|
| Additive effect of erythropoietin and heme on murine hematopoietic recovery after azidothymidine treatment. | 1993-12-15 |
|
| Long-term bone marrow stromal and hemopoietic toxicity to AZT: protective role of heme and IL-1. | 1993-02 |
|
| Heme inhibits human immunodeficiency virus 1 replication in cell cultures and enhances the antiviral effect of zidovudine. | 1991-03-01 |
Patents
Sample Use Guides
The matrix fraction of rat liver mitochondria has a high binding capacity for protoheme IX with an almost linear increase in binding up to at least 28 nmol heme/mg protein. Since free heme could not be detected until the heme to protein ratio exceeded 14 nmol heme/mg protein, it is suggested that there is a substantial high-affinity binding of heme to matrix components, probably those of high molecular weight and low electrophoretic mobility.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:17:31 GMT 2025
by
admin
on
Mon Mar 31 20:17:31 GMT 2025
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| Record UNII |
42VZT0U6YR
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| Record Status |
Validated (UNII)
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| Record Version |
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EU-Orphan Drug |
EU/3/13/1149
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NCI_THESAURUS |
C764
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FDA ORPHAN DRUG |
402413
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SUB14075MIG
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C538
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HEME B
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60344
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17627
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30413
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D006418
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42VZT0U6YR
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26355
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m5944
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267100
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14875-96-8
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DTXSID90889386
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SUB30447
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100000093418
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