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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:48 UTC
HMDB IDHMDB0001162
Secondary Accession Numbers
  • HMDB01162
Metabolite Identification
Common NameHeme O
DescriptionHeme O differs from the closely related heme A by having a methyl group at ring position 8 instead of the formyl group, the isoprenoid chain at position 2 is the same (Wikipedia).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC49H58FeN4O5
Average Molecular Weight838.854
Monoisotopic Molecular Weight838.375663119
IUPAC Name3-[(11Z,16Z)-20-(2-carboxyethyl)-15-ethenyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,4,6(25),7,9,11,13(24),14,16,18-undecaen-4-yl]propanoic acid
Traditional Name3-[(11Z,16Z)-20-(2-carboxyethyl)-15-ethenyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,4,6(25),7,9,11,13(24),14,16,18-undecaen-4-yl]propanoic acid
CAS Registry Number137397-56-9
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C5/C=C6\N=C(\C=C\1/N\2[Fe]N45)C(C)=C6C=C)/C(CCC(O)=O)=C3C
InChI Identifier
InChI=1S/C49H60N4O5.Fe/c1-10-35-31(6)40-26-45-49(46(54)19-13-18-30(5)17-12-16-29(4)15-11-14-28(2)3)34(9)41(53-45)24-38-32(7)36(20-22-47(55)56)43(51-38)27-44-37(21-23-48(57)58)33(8)39(52-44)25-42(35)50-40;/h10,14,16,18,24-27,46,54H,1,11-13,15,17,19-23H2,2-9H3,(H4,50,51,52,53,55,56,57,58);/q;+2/p-2/b29-16+,30-18+,38-24-,39-25-,40-26-,41-24-,42-25-,43-27-,44-27-,45-26-;
InChI KeyFISPASSVCDRERW-KVGORYHISA-L
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct ParentMetallotetrapyrroles
Alternative Parents
Substituents
  • Metallotetrapyrrole skeleton
  • Diterpenoid
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Ketimine
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Metalloheterocycle
  • Azacycle
  • Organic metal salt
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic transition metal salt
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic salt
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
logP6.21ALOGPS
logP11.26ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)2.84ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130.47 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity237.91 m³·mol⁻¹ChemAxon
Polarizability96.53 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009l-0000000970-0ab5b5c8236aeb83353aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00s6-1200001930-2056d7e5ba2335a6154bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-1100000900-fb1e1bfe680d13bc4e01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000390-fc9d0bdfd86ce5bb111eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0171-2120061950-c114e5cb2af8c6ea5b24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fs-0000090410-19e8eef5041c9549ea3fView in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acute Intermittent PorphyriaPw000174Pw000174 greyscalePw000174 simpleNot Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseasePw000176Pw000176 greyscalePw000176 simpleNot Available
Hereditary Coproporphyria (HCP)Pw000211Pw000211 greyscalePw000211 simpleNot Available
Porphyria Variegata (PV)Pw000175Pw000175 greyscalePw000175 simpleNot Available
Porphyrin MetabolismPw000158Pw000158 greyscalePw000158 simpleMap00860
Displaying all 5 entries
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022457
KNApSAcK IDNot Available
Chemspider ID3571849
KEGG Compound IDC15672
BioCyc IDHEME_O
BiGG IDNot Available
Wikipedia LinkHeme O
METLIN ID6044
PubChem Compound0
PDB IDNot Available
ChEBI ID24480
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in protoheme IX farnesyltransferase activity
Specific function:
Converts protoheme IX and farnesyl diphosphate to heme O (By similarity).
Gene Name:
COX10
Uniprot ID:
Q12887
Molecular weight:
Not Available
Reactions
Heme + Water + Farnesyl pyrophosphate → Heme O + Pyrophosphatedetails
General function:
Involved in protein complex assembly
Specific function:
May be involved in the biosynthesis of heme A.
Gene Name:
COX15
Uniprot ID:
Q7KZN9
Molecular weight:
Not Available
Reactions
Heme O → Heme Adetails