N-Acetyl-L-Citrulline

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Basic information

CAS: 33965-42-3
Standard SMILES: CC(=O)N[C@@H](CCCNC(N)=O)C(=O)O
InChIKey: WMQMIOYQXNRROC-LURJTMIESA-N
Molecular formula: C8H15N3O4
Average molar mass: 217.22 g/mol
Monoisotopic mass: 217.10625597

Overview

N-acetyl-L-citrulline is the L-enantiomer of N-acetylcitrulline. It is a N-acetyl-L-amino acid and a N-acetylcitrulline. It is functionally related to a L-citrulline. It is a conjugate acid of a N-acetyl-L-citrullinate.

Names & identifiers

Preferred name: N-Acetyl-L-Citrulline
IUPAC: (2S)-2-acetamido-5-(carbamoylamino)pentanoic acid
English name: N-Acetyl-L-citrulline
Molecular formula: C8H15N3O4
Molecular weight: 217.22

Names & synonyms

N-ACETYL-L-CITRULLINE(S)-2-ACETAMIDO-5-UREIDOPENTANOIC ACID(2S)-2-acetamido-5-(carbamoylamino)pentanoic acidalpha-N-Acetylcitrullineacetyl-citrullineN(2)-acetyl-N(5)-carbamoyl-L-ornithine(2S)-2-(acetylamino)-5-[(aminocarbonyl)amino]pentanoic acid(2S)-5-(carbamoylamino)-2-acetamidopentanoic acidN5-acetylcarbamoyl-L-ornithineCHEBI:49002DTXSID30349676(2S)-2-(acetylamino)-5-((aminocarbonyl)amino)pentanoic acid

Show more names

AC-L-citrullineN-acetylcitrullineL-Ornithine, N2-acetyl-N5-(aminocarbonyl)-2-acetamido-5-(carbamoylamino)pentanoic acid

RefChem:828880DTXCID70300746(2S)-2-acetamido-5-(carbamoylamino)pentanoic acid;N(2)-acetyl-N(5)-carbamoyl-L-ornithine974-935-633965-42-3N-a-Acetylcitrulline(2S)-2-Acetamido-5-ureido-pentanoic acidMFCD12407169

Database identifiers

CAS

Properties

Computed structural properties

XLogP: -2.3
Topological polar surface area: 122 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 4
Rotatable bonds: 6
Heavy atoms: 15
Formal charge: 0
Complexity: 254

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionSolid

Physicochemical properties

Melting point: 55 · 55 - 56°C
Boiling point: 531.4 · 531.4±50.0 °C(Predicted)
Density: 1.269 · 1.269
storage temp.: -20 °C · -20°C Freezer, Under inert atmosphere
solubility: Methanol (Slightly), Water (Slightly)
pka: 3.63 · 3.63±0.10(Predicted)
form: Solid
color: White to Off-White
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338

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 · 4 items

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)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Applications

Uses(S)-2-Acetamido-5-ureidopentanoic Acid can be used in anti-integrim biologic therapy for inflammatory bowel diseases.

Additional notes

DefinitionChEBI: An N-acetyl-amino acid that is the Nalpha-acetyl derivative of citrulline.

Related reactions

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Compound notes

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