Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Aquacobalamin (HMDB03458)

Blood
Urine

Record Information

Version

3.5

Creation Date

2006-08-12 15:24:55 -0600

Update Date

2013-02-08 17:12:35 -0700

HMDB ID

HMDB03458

Secondary Accession Numbers

HMDB06473

Metabolite Identification

Common Name

Aquacobalamin

Description

Aquacobalamin is one of the major forms of vitamin B(12) isolated from mammalian cells. Aquacobalamin and the thiolate forms of glutathione are the precursors of glutathionylcobalamin (GSCbl, a precursor to the formation of the two coenzyme forms of vitamin B(12), adenosylcobalamin and methylcobalamin) in mammalian cells. Under biological conditions the formation of GSCbl from aquacobalamin and glutathione is essentially irreversible; upon entering cells, any free (protein-unbound) aquacobalamin could be rapidly and irreversibly converted to GSCbl. (PMID: 15476387 Link_out

). Aquacobalamin is reduced to cob(II)alamin by Methionine synthase reductse (MSR) in the presence of NADPH, and this reduction leads to stimulation of the conversion of apomethionine synthase and aquacobalamin to methionine synthase holoenzyme. MSR serves as a special chaperone for human methionine synthase and as an aquacobalamin reductase, rather than acting solely in the reductive activation of methionine synthase. (PMID: 16769880 Link_out

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Aquacob(III)alamin
Aquocobalamin
Aquocobalamin hydroxide
Aquocobalamine
Coalpha-[alpha-(5,6-dimethylbenzimidazolyl)]-Cobeta-aquacobamide Vitamin-B12a

Chemical Formula

C₆₂H₉₀CoN₁₃O₁₅P

Average Molecular Weight

1347.3631

Monoisotopic Molecular Weight

1346.574895981

IUPAC Name

(10S,12R,13S,17R,23R,24R,30S,35S,36S,40S,41S,42R,46R)-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-1,15,46-trihydroxy-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

Traditional IUPAC Name

CAS Registry Number

13422-52-1

SMILES

C(C(N)=O)C[C@H]1[C@@](C2=C(C)C3=[N]4[C@]([C@@](CC(N)=O)([C@@H]3CCC(N)=O)C)(C3[C@H](CC(N)=O)[C@@]5(C6=C(C)C7=[N]8[Co+]4([N]4=CN([C@H]9O[C@@H]([C@@H](OP(O[C@@H](CNC(CC5)=O)C)(O)=O)[C@H]9O)CO)C5=C4C=C(C(=C5)C)C)([N]2=C1C=C8C(C)(C)[C@@H]7CCC(N)=O)(N36)O)C)C)(CC(N)=O)C

InChI Identifier

InChI=1S/C62H90N13O14P.Co.H2O/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;;/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);;1H2/q;+3;/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;;/m1../s1

InChI Key

YOZNUFWCRFCGIH-UVKKECPRSA-L

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Aromatic Heteropolycyclic Compounds

Class

Tetrapyrroles and Derivatives

Sub Class

Metallotetrapyrroles

Other Descriptors

Corrinoids
Organic Compounds

Substituents

Benzimidazole
Carboxamide Group
Diterpene
Enamine
Imidazole
Imine
Lactam
Organic Hypophosphite
Organic Phosphite
Organic Transition Metal Moeity
Organometallic Compound
Oxolane
Phosphoric Acid Ester
Primary Alcohol
Primary Carboxylic Acid Amide
Pyrrolidine
Pyrroline
Quaternary Ammonium Salt
Secondary Alcohol
Secondary Carboxylic Acid Amide
Toluene

Direct Parent

Metallotetrapyrroles

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Lipid biosynthesis, Fatty acid transport

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
LogP	1.09	ALOGPS
LogS	-4.90	ALOGPS
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	496.64 A²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	352.14	ChemAxon
Polarizability	135.41	ChemAxon
Formal Charge	1	ChemAxon
Physiological Charge	1	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biofluid Locations

Blood

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Comments
Blood	Detected and Quantified	0.00037 (0.000087-0.00150) uM	Newborn (0-30 days old)	Not Specified	Normal	Not Available
Blood	Detected and Quantified	0.000136 (0.00004-0.00050) uM	Children (1-13 year old)	Not Specified	Normal	Not Available
Blood	Detected and Quantified	0.00028 +/- 0.00012 uM	Adult (>18 years old)	Female	Normal	Not Available
Blood	Detected and Quantified	0.00030 (0.00013-0.00075) uM	Adult (>18 years old)	Male	Normal	Not Available