2.0 2012-05-31 13:58:01 -0600 2015-06-03 15:54:20 -0600 ECMDB03178 M2MDB000481 Heme Heme B or haem B (also known as protoheme IX) is the most abundant heme in nature. E. coli is known to produce 4 different hemes: protoheme IX (heme B), heme C, heme D, and siroheme. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins. Generally, heme B is attached to the surrounding protein matrix (known as the apoprotein) through a single coordination bond between the heme iron and an amino-acid side-chain. When oxygen is bound the iron becomes hexacoordinated. Since the iron in heme B containing proteins is bound to the four nitrogens of the porphyrin (forming a plane) and a single electron donating atom of the protein, the iron is often in a pentacoordinate state. (protoporphyrinato)iron Ferroheme Ferroheme b Ferroprotoheme Ferroprotoporphyrin Ferroprotoporphyrin IX Ferrous protoheme Ferrous protoheme IX Haem Hem Heme Heme <i>b</i> Heme b Iron protoporphyrin Iron protoporphyrin IX Iron(II) protoporphyrin IX Protoferroheme Protohaem Protoheme Protoheme IX Reduced hematin C34H32FeN4O4 616.487 616.177297665 4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide 4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide 14875-96-8 CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C=C)C(C)=C6C=C7C(C=C)=C(C)C8=[N+]7[Fe@]4(N2C1=C8)N56)C(C)=C3CCC(O)=O 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;+4/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-; YHLKGEDAGPGZPN-RGGAHWMASA-L Solid Cytosol Extra-organism Membrane Periplasm logp -1.01 ALOGPS logs -5.48 ALOGPS solubility 2.42e-03 g/l ALOGPS logp 2.19 ChemAxon pka_strongest_acidic 3.35 ChemAxon iupac 4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide ChemAxon average_mass 616.487 ChemAxon mono_mass 616.177297665 ChemAxon smiles CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C=C)C(C)=C6C=C7C(C=C)=C(C)C8=[N+]7[Fe@]4(N2C1=C8)N56)C(C)=C3CCC(O)=O ChemAxon formula C34H32FeN4O4 ChemAxon 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;+4/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-; ChemAxon inchikey YHLKGEDAGPGZPN-RGGAHWMASA-L ChemAxon polar_surface_area 92.22 ChemAxon refractivity 169.77 ChemAxon polarizability 69.44 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 ABC transporters ec02010 Metabolic pathways eco01100 heme biosynthesis from uroporphyrinogen-III I HEME-BIOSYNTHESIS-II superpathway of heme biosynthesis from uroporphyrinogen-III PWY0-1415 heme biosynthesis from uroporphyrinogen-III II HEMESYN2-PWY Specdb::CMs 103503 Specdb::CMs 103504 Specdb::CMs 540170 Specdb::CMs 540171 Specdb::CMs 540172 Specdb::CMs 540173 Specdb::CMs 792693 Specdb::NmrOneD 135300 Specdb::NmrOneD 135301 Specdb::NmrOneD 135302 Specdb::NmrOneD 135303 Specdb::NmrOneD 135304 Specdb::NmrOneD 135305 Specdb::NmrOneD 135306 Specdb::NmrOneD 135307 Specdb::NmrOneD 135308 Specdb::NmrOneD 135309 Specdb::NmrOneD 135310 Specdb::NmrOneD 135311 Specdb::NmrOneD 135312 Specdb::NmrOneD 135313 Specdb::NmrOneD 135314 Specdb::NmrOneD 135315 Specdb::NmrOneD 135316 Specdb::NmrOneD 135317 Specdb::NmrOneD 135318 Specdb::NmrOneD 135319 Specdb::MsMs 1223065 Specdb::MsMs 1223066 Specdb::MsMs 1223067 Specdb::MsMs 1338706 Specdb::MsMs 1338707 Specdb::MsMs 1338708 Specdb::MsMs 2302812 Specdb::MsMs 2302813 Specdb::MsMs 2302814 Specdb::MsMs 3066725 Specdb::MsMs 3066726 Specdb::MsMs 3066727 HMDB03178 26945 C00032 17627 PROTOHEME Heme Keseler, I. 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Mutat Res. 2003 Dec 9;542(1-2):89-97. 14644357 Ferrochelatase P23871 HEMH_ECOLI hemH http://ecmdb.ca/proteins/P23871.xml Cytochrome c biogenesis ATP-binding export protein CcmA P33931 CCMA_ECOLI ccmA http://ecmdb.ca/proteins/P33931.xml Heme exporter protein C P0ABM1 CCMC_ECOLI ccmC http://ecmdb.ca/proteins/P0ABM1.xml Heme exporter protein B P0ABL8 CCMB_ECOLI ccmB http://ecmdb.ca/proteins/P0ABL8.xml Heme exporter protein D P0ABM5 CCMD_ECOLI ccmD http://ecmdb.ca/proteins/P0ABM5.xml Protoheme IX farnesyltransferase P0AEA5 CYOE_ECOLI cyoE http://ecmdb.ca/proteins/P0AEA5.xml Cytochrome c-type biogenesis protein CcmE P69490 CCME_ECOLI ccmE http://ecmdb.ca/proteins/P69490.xml Adenosine triphosphate + Water + Heme > ADP + Hydrogen ion + Phosphate + Heme TRANS-RXN0-162 Adenosine triphosphate + Water + Heme > ADP + Hydrogen ion + Phosphate + Heme TRANS-RXN0-162 Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate R07411 HEMEOSYN-RXN Iron + Protoporphyrin IX >2 Hydrogen ion + Heme PROTOHEMEFERROCHELAT-RXN Protoporphyrin IX + Fe2+ <> Heme +2 Hydrogen ion + Fe2+ R00310 Heme + Water + Farnesyl pyrophosphate <> Heme O + Pyrophosphate R07411 HEMEOSYN-RXN Heme + Hydrogen peroxide Heme D RXN-8073 Hydrogen ion + Heme Protoporphyrin IX + Iron RXN0-6258 Iron + Protoporphyrin IX > Heme + Hydrogen ion PROTOHEMEFERROCHELAT-RXN Heme + Adenosine triphosphate + Water > Phosphate + ADP + Heme + Hydrogen ion TRANS-RXN0-162 Heme + Adenosine triphosphate + Water > Phosphate + ADP + Heme + Hydrogen ion TRANS-RXN0-162 Heme + 2 Hydrogen ion > Protoporphyrin IX + Iron ADP + Phosphate + 4 Hydrogen ion + Heme + Nickel(2+) + Iron chelate + Taurine + Molybdate + Magnesium + Fe3+ + Potassium + Polyamine + vitamin B12 + Sulfate + glycerol-3-phosphate + Phosphonate + D-Maltose <> Adenosine triphosphate +3 Hydrogen ion + Water R00086 RXN0-1061 Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate Protoporphyrin IX + Fe2+ <> Heme +2 Hydrogen ion Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate