ChemFOnt: Showing chemical card for Lipoyl-GMP (CFc000008510)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:19 UTC

Chemfont ID

CFc000008510

Molecule Identification

Common Name

Lipoyl-GMP

Definition

Lipoyl-GMP is an intermediate in lipoic acid metabolism.In mammals, the posttranslational modification of unlipoylated apoproteins by addition of lipoic acid is done in a two-step enzymatic reaction using free lipoic acid. The free lipoic acid in the cell is first activated by reacting it. with adenosine triphosphate, using up two high energy phosphate bonds to form lipoyl-AMP (GMP), a process catalyzed by lipoate activating enzyme (LAE).41 The activated lipoyl moiety is subsequently used to form an amide bond with lysine residues of the unlipoylated apoprotein, which is catalyzed by lipoyl-AMP(GMP):N-lysine lipoyl transferase Interestingly, purified LAE from bovine liver mitochondria preferentially utilizes guanosine triphosphate, instead of adenosine triphosphate, for the activation of lipoic acid to form lipoyl-GMP.44 Furthermore, genetic analysis of LAE reveals that the enzyme is identical to. xenobiotic-metabolizing/medium-chain fatty acid:CoA ligase-III (XL-III) (also from bovine liver mitochondria). 44 Hence, there appear to be two pathways in which LAE is capable of activating carboxylic acids: one that uses guanosine triphosphate to form acyl-GMP; the other is dependent on adenosine triphosphate for the activation of carboxylic acids to the CoA thioester (acyl-CoA) via an. acyl-AMP intermediate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₈H₂₆N₅O₉PS₂

Average Molecular Weight

551.531

Monoisotopic Molecular Weight

551.090955347

IUPAC Name

{[(2R,3S,4R,5R)-5-{2-[5-(1,2-dithiolan-3-yl)pentanamido]-6-oxo-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-{2-[5-(1,2-dithiolan-3-yl)pentanamido]-6-oxo-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

None

SMILES

O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(NC(=O)CCCCC1CCSS1)NC2=O

InChI Identifier

InChI=1S/C18H26N5O9PS2/c24-11(4-2-1-3-9-5-6-34-35-9)20-18-21-15-12(16(27)22-18)19-8-23(15)17-14(26)13(25)10(32-17)7-31-33(28,29)30/h8-10,13-14,17,25-26H,1-7H2,(H2,28,29,30)(H2,20,21,22,24,27)/t9?,10-,13-,14-,17-/m1/s1

InChI Key

DVZGUOFXTLKZTJ-LQLSJNDNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Lipoamide
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
N-arylamide
Monoalkyl phosphate
Pyrimidone
Fatty acyl
Fatty amide
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Tetrahydrofuran
1,2-dithiolane
Heteroaromatic compound
Dithiolane
Imidazole
Vinylogous amide
Azole
Secondary alcohol
Organic disulfide
Secondary carboxylic acid amide
1,2-diol
Carboxamide group
Organoheterocyclic compound
Oxacycle
Azacycle
Carboxylic acid derivative
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0013617)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120439)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120523)
3-Methylglutaconic Aciduria Type I (PathBank: SMP0120663)
Beta-Ketothiolase Deficiency (PathBank: SMP0120679)
3-Hydroxyisobutyric Aciduria (PathBank: SMP0120806)
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I (PathBank: SMP0120441)
3-Methylglutaconic Aciduria Type IV (PathBank: SMP0120444)
Methylmalonic Aciduria (PathBank: SMP0120525)
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency (PathBank: SMP0120661)
3-Methylglutaconic Aciduria Type III (PathBank: SMP0120664)
Isovaleric Acidemia (PathBank: SMP0120808)
Maple Syrup Urine Disease (PathBank: SMP0120516)
Propionic Acidemia (PathBank: SMP0120537)
Isobutyryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120588)
Isovaleric Aciduria (PathBank: SMP0120723)
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency (PathBank: SMP0120586)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000137)

Metabolic pathway

Valine, Leucine, and Isoleucine Degradation (PathBank: SMP0063689)
Valine, Leucine, and Isoleucine Degradation (HMDB: HMDB0013617)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.12 g/L	ALOGPS
logP	0.55	ALOGPS
logP	-0.86	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.29	ChemAxon
pKa (Strongest Basic)	0.36	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	126.67 m³·mol⁻¹	ChemAxon
Polarizability	52.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0013617

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029596

KNApSAcK ID

Not Available

Chemspider ID

35032769

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481910

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Lipoyl-GMP (CFc000008510)

MOL for CFc000008510 (Lipoyl-GMP)

3D MOL for CFc000008510 (Lipoyl-GMP)

3D SDF for CFc000008510 (Lipoyl-GMP)

3D-SDF for CFc000008510 (Lipoyl-GMP)

PDB for CFc000008510 (Lipoyl-GMP)

3D PDB for CFc000008510 (Lipoyl-GMP)

SMILES for CFc000008510 (Lipoyl-GMP)

INCHI for CFc000008510 (Lipoyl-GMP)

Structure for CFc000008510 (Lipoyl-GMP)

3D Structure for CFc000008510 (Lipoyl-GMP)