Showing Metabocard for adenosylcob(III)alamin (BASm0001269)

Common NameAdenosylcob(iii)alamin
DescriptionAdenosylcobalamin is one of two metabolically active forms synthesized upon ingestion of vitamin B12 and is the predominant form in the liver; it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase. A cobalamin (cbl) derivative in which the substituent is deoxyadenosyl. It is one of two metabolically active forms synthesized upon ingestion of vitamin B12 and is the predominant form in the liver; it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase (MCM; E.C. 5.4.99.2). Inborn errors of vitamin B12 metabolism are autosomal recessive disorders and have been classified into nine distinct complementation classes. Disorders affecting adenosylcobalamin cause methylmalonic acidemia and metabolic acidosis. Methylmalonyl-CoA mutase catalyzes the conversion of L-methylmalonyl-CoA to succinyl-CoA and uses adenosylcobalamin (AdoCbl) as a cofactor. Cbl must be transported into mitochondria, reduced and adenosylated before it can be utilized by MCM. (PMID: 17011224 ).
Structure
Molecular FormulaC72H100CoN18O17P
Average Mass1579.58180
Monoisotopic Mass1578.65835
IUPAC Name(10S,12R,13S,17R,23R,24R,30S,35S,36S,40S,41S,42R,46R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2$l^{4},9,19,26,43$l^{4},44$l^{4},45$l^{4}-heptaaza-15$l^{5}-phospha-1-cobaltadodecacyclo[27.14.1.1^{1,34}.1^{2,9}.1^{10,13}.0^{1,26}.0^{3,8}.0^{23,27}.0^{25,42}.0^{32,44}.0^{39,43}.0^{37,45}]heptatetraconta-2(47),3(8),4,6,27,29(44),32,34(45),37,39(43)-decaen-1-ylium-15-olate
Traditional Name(10s,12r,13s,17r,23r,24r,30s,35s,36s,40s,41s,42r,46r)-1-{[(2s,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-unde
CAS Registry Number13870-90-1
SMILESCC1=C2N3[C@@H]4[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(=O)([O-])O[C@H]2[C@@H](O)[C@H](O[C@@H]2CO)n2c[n+](c5cc(C)c(C)cc52)[Co-3]325(C[C@H]3O[C@@H](n6cnc7c(N)ncnc76)[C@H](O)[C@@H]3O)[N+]3=C1[C@@H](CCC(N)=O)C(C)(C)C3=CC1=[N+]2C(=C(C)C2=[N+]5[C@]4(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]1CCC(N)=O
InChI IdentifierInChI=1S/C62H90N13O14P.C10H12N5O3.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1
InChI KeyZIHHMGTYZOSFRC-OUCXYWSSSA-L
CHEBI IDCHEBI:18408
HMDB IDHMDB0002086
Pathways
NameSMPDB/PathBank
Propanoate metabolism
Valine, leucine and isoleucine degradation
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency
3-Methylglutaconic Aciduria Type I
3-Methylglutaconic Aciduria Type III
3-Methylglutaconic Aciduria Type IV
Beta-Ketothiolase Deficiency
Malonic Aciduria
Maple Syrup Urine Disease
Methylmalonic Aciduria
Methylmalonic Aciduria Due to Cobalamin-Related Disorders
Propionic Acidemia
3-Methylcrotonyl Coa Carboxylase Deficiency Type I
Isovaleric Aciduria
Methylmalonate Semialdehyde Dehydrogenase Deficiency
Threonine and 2-Oxobutanoate Degradation
Malonyl-coa decarboxylase deficiency
3-hydroxyisobutyric acid dehydrogenase deficiency
3-hydroxyisobutyric aciduria
Isobutyryl-coa dehydrogenase deficiency
Isovaleric acidemia
StateNot Available
Water Solubility6.85e-02 g/l
logP0.37
logS-4.38
pKa (Strongest Acidic)Not Available
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count0
Hydrogen Donor Count0
Polar Surface Area598.55 Ų
Rotatable Bond Count19
Physiological Charge0
Formal Charge0
Refractivity408.83 m³·mol⁻¹
Polarizability158.83

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