Basic information
- CAS
3715-10-4- Standard SMILES
NC(N)=NCCCC(=O)C(=O)O- InChIKey
ARBHXJXXVVHMET-UHFFFAOYSA-N- Molecular formula
- C6H11N3O3
- Average molar mass
- 173.17 g/mol
- Monoisotopic mass
- 173.08004122
Overview
5-guanidino-2-oxopentanoic acid is a 2-oxo monocarboxylic acid that is 2-oxopentanoic acid in which one of the methyl hydrogens is substituted by a carbamimidamido group. It has a role as a mouse metabolite and a human metabolite. It is functionally related to a valeric acid. It is a conjugate acid of a 5-guanidino-2-oxopentanoate. It is a tautomer of a 5-guanidino-2-oxopentanoic acid zwitterion.
Names & identifiers
- Preferred name
- alpha-keto-delta-Guanidinovaleric acid
- IUPAC
- 5-(diaminomethylideneamino)-2-oxopentanoic acid
- English name
- 5-(diaminomethylideneamino)-2-oxo-pentanoic acid
- Molecular formula
- C6H11N3O3
- Molecular weight
- 173.17
Names & synonyms
3715-10-45-carbamimidamido-2-oxopentanoic acidalpha-Keto-delta-guanidinovaleric acid2-Oxo-5-guanidinovaleric acidDTXSID001906325-((Aminoiminomethyl)amino)-2-oxopentanoic acidRefChem:555765DTXCID40113123847-966-72-oxoarginine5-guanidino-2-oxopentanoic aciddelta-Guanido-a-ketovaleric Acid
Show more names
-Guanido-α-ketovalericAcidAKA 2-OxoarginineArginine Impurity 33δ-Guanido-α-ketovaleric Acidδ-Guanido-α-ketovaleric Acidα-keto-δ-Guanidinovaleric acid
2-Oxo-5-guanidinopentanoate5-(diaminomethylideneamino)-2-oxopentanoic acid5-Guanidino-2-oxo-pentanoate5-[(diaminomethylidene)amino]-2-oxopentanoic acid2-Oxo-5-guanidino-pentanoate5-(DIAMINOMETHYLIDENEAMINO)-2-OXO-PENTANOIC ACIDdelta-Guanido-alpha-ketovaleric acid5-Guanidino-2-oxovaleric acid
Database identifiers
- CAS
3715-10-4
Properties
Computed structural properties
- XLogP
- -1.6
- Topological polar surface area
- 119 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 208
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 350 °C · >350 °C
- Boiling point
- 331.8 · 331.8±44.0 °C(Predicted)
- Density
- 1.45 · 1.45±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Very Slightly, Heated), Water (Slightly)
- form
- Solid
- pka
- 2.54 · 2.54±0.54(Predicted)
- color
- White to Off-White
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 335 · H335-H319-H315
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary
Uremic toxins such as alpha-keto-delta-guanidinoacetic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).
Chemistry & industry
Pharmacology
Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Cellular LocationsExtracellular
Metabolite PathwaysD-Arginine and D-Ornithine Metabolism
Uses & manufacturing
UsesNaturally produced by the body (endogenous).
Applications
Usesδ-Guanido-α-ketovaleric Acid is a useful flavouring ingredient and a component of Cheddar cheese flavour.
Suppliers13 total
艾吉析科技（上海）有限公司17717235263 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
TargetMol 中国（陶术生物）400-821-0310 15002144251 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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