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Record Information
Version4.0
Creation Date2008-08-15 14:42:52 UTC
Update Date2017-09-27 08:24:49 UTC
HMDB IDHMDB0006902
Secondary Accession Numbers
  • HMDB06902
  • HMDB06966
Metabolite Identification
Common NameCobinamide
DescriptionCobinamide is an intermediate in porphyrin and chlorophyll metabolism. It is converted to adenosyl cobinamide via the enzyme cob(I)alamin adenosyltransferase [EC:2.5.1.17]. Adenosyl cobinamide is the third to last step in the synthesis of vitamin B12 coenzyme.
Structure
Thumb
Synonyms
ValueSource
CbiChEBI
Cob(I)inamideChEBI
CobinamidChEBI
Cobinamide dihydrateHMDB
DiaquocobinamideHMDB
Chemical FormulaC48H72CoN11O8
Average Molecular Weight990.0874
Monoisotopic Molecular Weight989.489733529
IUPAC Name[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-hydroxypropyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltbis(ylium)
Traditional Name[(1R,2R,3S,4S,8S,9S,14S,18R,19R)-4,9,14-tris(2-carbamoylethyl)-3,8,19-tris(carbamoylmethyl)-18-(2-{[(2R)-2-hydroxypropyl]carbamoyl}ethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltbis(ylium)
CAS Registry Number13497-85-3
SMILES
C[C@@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co++])\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N
InChI Identifier
InChI=1S/C48H73N11O8.Co/c1-23(60)22-55-38(67)16-17-45(6)29(18-35(52)64)43-48(9)47(8,21-37(54)66)28(12-15-34(51)63)40(59-48)25(3)42-46(7,20-36(53)65)26(10-13-32(49)61)30(56-42)19-31-44(4,5)27(11-14-33(50)62)39(57-31)24(2)41(45)58-43;/h19,23,26-29,43,60H,10-18,20-22H2,1-9H3,(H14,49,50,51,52,53,54,55,56,57,58,59,61,62,63,64,65,66,67);/q;+3/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;/m1./s1
InChI KeyFEESAGIUMZGLMF-JFYQDRLCSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassTetrapyrroles and derivatives
Direct ParentMetallotetrapyrroles
Alternative Parents
Substituents
  • Metallotetrapyrrole skeleton
  • Fatty amide
  • Fatty acyl
  • Pyrrolidine
  • Pyrroline
  • Carboxamide group
  • Ketimine
  • Primary carboxylic acid amide
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carbene-type 1,3-dipolar compound
  • Azacycle
  • Carboxylic acid derivative
  • Organic transition metal salt
  • Alcohol
  • Organic cobalt salt
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Imine
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic cation
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

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 Solubility0.0052 g/LALOGPS
logP2.46ALOGPS
logP-3.2ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)15.28ChemAxon
pKa (Strongest Basic)8.8ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area348.19 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity252.9 m³·mol⁻¹ChemAxon
Polarizability101.7 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDFDB024149
KNApSAcK IDNot Available
Chemspider ID9702912
KEGG Compound IDC05774
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11528127
PDB IDNot Available
ChEBI ID28956
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
MMAB
Uniprot ID:
Q96EY8
Molecular weight:
27387.975
Reactions
Adenosine triphosphate + Cobinamide → Triphosphate + Adenosyl cobinamidedetails
Adenosine triphosphate + Cobinamide → PPPi + Adenosyl cobinamidedetails