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Adenosylcobalamin

CAT: 0931-T14128-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0931-T14128-01Size:10 mg
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CAS Number
13870-90-1
Target
Endogenous Metabolite
Related Pathways
Metabolism
Purity
0.9946
Bioactivity
Adenosylcobalamin (AdoCbl) is a biologically active form of vitamin B12 .It is a cofactor for methylmalonyl CoA mutase. It belongs to the corrinoid group of compounds, which contain a corrin macrocycle, and is produced only by certain bacteria and archaea. It is a cofactor for various enzymes including mutases, eliminases, aminomutases, and a reductase.
Smiles
Nc1ncnc2n(cnc12)[C@H]1O[C@H](C[Co++])[C@H](O)[C@@H]1O.[H][C@]12[N-]\C(=C(C)/C3=N/C(=C\C4=N\C(=C(C)/C5=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]5CCC(N)=O)\[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)/C(C)(C)[C@@H]3CCC(N)=O)[C@](C)(CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@@H]1[C@@H](CO)O[C@@H]([C@@H]1O)n1cnc3cc(C)c(C)cc13)[C@H]2CC(N)=O
Molecular Formula
C72H100CoN18O17P
Molecular Weight
1579.58
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Coenzyme B12

Adenosylcobalamin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).

CAS Number13870-90-1
PubChem CID6474320
IUPAC Name(2S,3S,4R,5R)-2-(6-aminopurin-9-yl)-5-methanidyloxolane-3,4-diol;cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,4Z,7S,9Z,12S,13S,14Z,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-21-id-3-yl]propanoylamino]propan-2-yl] phosphate
Molecular FormulaC72H100CoN18O17P
Molecular Weight1579.6
Topological Polar Surface Area571
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count27
Rotatable Bond Count27
Heavy Atom Count109
Formal Charge0
Complexity3730
SMILES
CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]\4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)/C(=C\7/[C@@]([C@@H](C(=N7)/C=C\8/C([C@@H](C(=N8)/C(=C4\[N-]5)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[CH2-][C@@H]1[C@@H]([C@@H]([C@H](O1)N2C=NC3=C(N=CN=C32)N)O)O.[Co+3]
InChI
InChI=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;-1;+3/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;4-,6+,7+,10+;/m11./s1
InChIKey
OAJLVMGLJZXSGX-SLAFOUTOSA-L
Chemical Structure
2D Structure
2D structure of Coenzyme B12
CAS: 13870-90-1
CID: 6474320
Formula: C72H100CoN18O17P
MW: 1579.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1579.6
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count27
Rotatable Bond Count27
Exact Mass1578.658339
Monoisotopic Mass1578.658339
Topological Polar Surface Area571 Ų
Heavy Atom Count109
Formal Charge0
Complexity3730
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes

Alternative Products

CatalogName
M22704-01Adenosylcobalamin
HY-112790R-01Adenosylcobalamin (Standard)
HY-107078DTPA-adenosylcobalamin
MBS1284349Recombinant Adenosylcobalamin-dependent ribonucleoside-triphosphate reductase (rtpR), partial
MBS1174904Recombinant Lactobacillus helveticus Adenosylcobalamin-dependent ribonucleoside-triphosphate reductase (rtpR), partial
MBS1412813Recombinant Euglena gracilis Adenosylcobalamin-dependent ribonucleoside-triphosphate reductase (rnr), partial
MBS1442998-01Recombinant Pseudomonas aeruginosa Bifunctional adenosylcobalamin biosynthesis protein CobP (cobP)
MBS1095452-01Recombinant Pseudomonas denitrificans Bifunctional adenosylcobalamin biosynthesis protein CobP (cobP)
MBS1039218-01Recombinant Escherichia coli Bifunctional adenosylcobalamin biosynthesis protein CobU (cobU)
MBS1190396Recombinant Nitratiruptor sp. Probable adenosylcobalamin-dependent ribonucleoside-triphosphate reductase (rtpR), partial

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