heme   Click here for help

GtoPdb Ligand ID: 4349

Synonyms: ferroheme | haem
Compound class: Metabolite or derivative
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES C=CC1=C(C)C2=NC1=Cc1[n-]c(c(c1C)CCC(=O)O)C=C1N=C(C=c3[n-]c(=C2)c(C=C)c3C)C(=C1CCC(=O)O)C.[Fe+2]
Isomeric SMILES C=CC1=C(C)C2=NC1=Cc1[n-]c(c(c1C)CCC(=O)O)C=C1N=C(C=c3[n-]c(=C2)c(C=C)c3C)C(=C1CCC(=O)O)C.[Fe+2]
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
InChI Key KABFMIBPWCXCRK-UHFFFAOYSA-L
References
1. Duffy SP, Shing J, Saraon P, Berger LC, Eiden MV, Wilde A, Tailor CS. (2010)
The Fowler syndrome-associated protein FLVCR2 is an importer of heme.
Mol Cell Biol, 30 (22): 5318-24. [PMID:20823265]
2. Matta-Camacho E, Banerjee S, Hughes TS, Solt LA, Wang Y, Burris TP, Kojetin DJ. (2014)
Structure of REV-ERBĪ² ligand-binding domain bound to a porphyrin antagonist.
J Biol Chem, 289 (29): 20054-66. [PMID:24872411]
3. Nakai Y, Inoue K, Abe N, Hatakeyama M, Ohta KY, Otagiri M, Hayashi Y, Yuasa H. (2007)
Functional characterization of human proton-coupled folate transporter/heme carrier protein 1 heterologously expressed in mammalian cells as a folate transporter.
J Pharmacol Exp Ther, 322 (2): 469-76. [PMID:17475902]
4. Quigley JG, Yang Z, Worthington MT, Phillips JD, Sabo KM, Sabath DE, Berg CL, Sassa S, Wood BL, Abkowitz JL. (2004)
Identification of a human heme exporter that is essential for erythropoiesis.
Cell, 118 (6): 757-66. [PMID:15369674]
5. Raghuram S, Stayrook KR, Huang P, Rogers PM, Nosie AK, McClure DB, Burris LL, Khorasanizadeh S, Burris TP, Rastinejad F. (2007)
Identification of heme as the ligand for the orphan nuclear receptors REV-ERBalpha and REV-ERBbeta.
Nat Struct Mol Biol, 14 (12): 1207-13. [PMID:18037887]
6. Yin L, Wu N, Curtin JC, Qatanani M, Szwergold NR, Reid RA, Waitt GM, Parks DJ, Pearce KH, Wisely GB et al.. (2007)
Rev-erbalpha, a heme sensor that coordinates metabolic and circadian pathways.
Science, 318 (5857): 1786-9. [PMID:18006707]