U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of FERROHEME

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-;

HIDE SMILES / InChI

Molecular Formula Fe
Molecular Weight 55.845
Charge 2
Count
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
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
Record UNII
42VZT0U6YR
Record Status Validated (UNII)
Record Version