ChemFOnt: Showing chemical card for Dimethylguanidino valeric acid (CFc000220476)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:35 UTC

Chemfont ID

CFc000220476

Molecule Identification

Common Name

Dimethylguanidino valeric acid

Definition

Dimethylguanidino valeric acid or DMGV is a product formed from the transamination of asymmetric dimethylarginine (ADMA) via the enzyme alanine-glyoxylate aminotransferase 2 (AGXT2). This pathway is involved in nitric oxide regulation. DMGV has been detected in both blood and urine (PMID: 21945966 ). More recently DMGV has been identified as an independent plasma biomarker of nonalcoholic fatty liver disease (NAFLD). Furthermore, plasma DMGV levels are correlated with biopsy-proven nonalcoholic steatohepatitis (NASH). Plasma DMGV levels have also been found to decline in parallel with improvements in post-procedure cardiometabolic parameters. Plasma DMGV levels have been shown to be able to predict the development of type 2 diabetes up to 12 years before disease onset (PMID: 29083323 ). Baseline plasma levels of DMGV have been shown to be positively associated with body fat percentage, abdominal visceral fat, very low-density lipoprotein cholesterol (VLDL), and triglycerides. Plasma levels of DMGV are inversely associated with insulin sensitivity, low-density lipoprotein cholesterol, high-density lipoprotein size, and high-density lipoprotein cholesterol (HDL). Overall, DMGV is associated with partial resistance to metabolic health benefits of regular exercise (PMID: 31166569 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DMGV	HMDB
5-[[(dimethylamino)iminomethyl]amino]-2-oxopentanoic acid	HMDB
α-keto-δ-(NG,NG-dimethylguanidino)valeric acid	HMDB
αlpha-keto-delta-(NG,NG-dimethylguanidino)valeric acid	HMDB
2-oxo-5-(3,3-Dimethylguanidine-1-yl)pentanoate	Generator, HMDB
(a-Keto-dimethyl-delta-N,N-dimethylguanidynol) valerate	Generator
(a-Keto-dimethyl-delta-N,N-dimethylguanidynol) valeric acid	Generator
(alpha-Keto-dimethyl-delta-N,N-dimethylguanidynol) valerate	Generator
(Α-keto-dimethyl-δ-N,N-dimethylguanidynol) valerate	Generator
(Α-keto-dimethyl-δ-N,N-dimethylguanidynol) valeric acid	Generator
Dimethylguanidinovaleric acid	HMDB
Dimethylguanidino valerate	HMDB
Dimethylguanidinovalerate	HMDB
2-oxo-5-(3,3-Dimethylguanidine-1-yl)pentanoic acid	HMDB
5-[[(dimethylamino)iminomethyl]amino]-2-oxopentanoate	HMDB
α-keto-δ-(NG,NG-dimethylguanidino)valerate	HMDB
alpha-keto-delta-(NG,NG-dimethylguanidino)valeric acid	HMDB
(alpha-keto-dimethyl-delta-N,N-Dimethylguanidynol)valerate	HMDB
(alpha-keto-dimethyl-delta-N,N-Dimethylguanidynol)valeric acid	HMDB

Chemical Formula

C₈H₁₅N₃O₃

Average Molecular Weight

201.226

Monoisotopic Molecular Weight

201.111341355

IUPAC Name

5-(N',N'-dimethylcarbamimidamido)-2-oxopentanoic acid

Traditional Name

5-(N',N'-dimethylcarbamimidamido)-2-oxopentanoic acid

CAS Registry Number

107347-90-0

SMILES

CN(C)C(=N)NCCCC(=O)C(O)=O

InChI Identifier

InChI=1S/C8H15N3O3/c1-11(2)8(9)10-5-3-4-6(12)7(13)14/h3-5H2,1-2H3,(H2,9,10)(H,13,14)

InChI Key

GLWRPXRMUUZNMD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Guanidine
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21945966)

Excreta

Biofluid or Excreta

Urine (PMID: 21945966)

Source

Exogenous

Exogenous (HMDB: HMDB0240212)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.37 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	-1.8	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.1	ChemAxon
pKa (Strongest Basic)	12.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.49 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.59 m³·mol⁻¹	ChemAxon
Polarizability	20.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240212

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00033966

Chemspider ID

58779677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101535539

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Dimethylguanidino valeric acid (CFc000220476)

MOL for CFc000220476 (Dimethylguanidino valeric acid)

3D MOL for CFc000220476 (Dimethylguanidino valeric acid)

3D SDF for CFc000220476 (Dimethylguanidino valeric acid)

3D-SDF for CFc000220476 (Dimethylguanidino valeric acid)

PDB for CFc000220476 (Dimethylguanidino valeric acid)

3D PDB for CFc000220476 (Dimethylguanidino valeric acid)

SMILES for CFc000220476 (Dimethylguanidino valeric acid)

INCHI for CFc000220476 (Dimethylguanidino valeric acid)

Structure for CFc000220476 (Dimethylguanidino valeric acid)

3D Structure for CFc000220476 (Dimethylguanidino valeric acid)