N-Acetyl-L-Citrulline

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates
Name
N-Acetyl-L-Citrulline
Accession Number
DB02368  (EXPT02432)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 217.2224
Monoisotopic: 217.106255983
Chemical Formula
C8H15N3O4
InChI Key
WMQMIOYQXNRROC-LURJTMIESA-N
InChI
InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)/t6-/m0/s1
IUPAC Name
(2S)-5-(carbamoylamino)-2-acetamidopentanoic acid
SMILES
CC(=O)N[C@@H](CCCNC(N)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UN-acetylornithine carbamoyltransferaseNot AvailableXanthomonas campestris pv. campestris (strain ATCC 33913 / NCPPB 528 / LMG 568)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C15532
PubChem Compound
656979
PubChem Substance
46506512
ChemSpider
571213
ChEBI
49002
HET
OLN
PDB Entries
3kzk

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.57 mg/mLALOGPS
logP-2ALOGPS
logP-1.9ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.52 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity50.77 m3·mol-1ChemAxon
Polarizability21.5 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5313
Blood Brain Barrier+0.9165
Caco-2 permeable-0.8278
P-glycoprotein substrateNon-substrate0.5218
P-glycoprotein inhibitor INon-inhibitor0.968
P-glycoprotein inhibitor IINon-inhibitor0.9719
Renal organic cation transporterNon-inhibitor0.9455
CYP450 2C9 substrateNon-substrate0.7055
CYP450 2D6 substrateNon-substrate0.7978
CYP450 3A4 substrateNon-substrate0.7317
CYP450 1A2 substrateNon-inhibitor0.9367
CYP450 2C9 inhibitorNon-inhibitor0.8971
CYP450 2D6 inhibitorNon-inhibitor0.9649
CYP450 2C19 inhibitorNon-inhibitor0.8969
CYP450 3A4 inhibitorNon-inhibitor0.7553
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.986
Ames testNon AMES toxic0.7118
CarcinogenicityNon-carcinogens0.9188
BiodegradationReady biodegradable0.9769
Rat acute toxicity1.6137 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9824
hERG inhibition (predictor II)Non-inhibitor0.9697
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-L-alpha-amino acids
Alternative Parents
Fatty acids and conjugates / Acetamides / Ureas / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
N-acyl-l-alpha-amino acid / Fatty acid / Acetamide / Carboxamide group / Carbonic acid derivative / Secondary carboxylic acid amide / Urea / Carboxylic acid / Monocarboxylic acid or derivatives / Organopnictogen compound
show 8 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
N-acetyl-L-amino acid, N-acetylcitrulline (CHEBI:49002)

Targets

Kind
Protein
Organism
Xanthomonas campestris pv. campestris (strain ATCC 33913 / NCPPB 528 / LMG 568)
Pharmacological action
Unknown
General Function
N-acetylornithine carbamoyltransferase activity
Specific Function
Catalyzes the conversion of N-acetylornithine to N-acetylcitrulline in an alternative arginine biosynthesis pathway. The enzyme has no activity with ornithine.
Gene Name
argF'
Uniprot ID
Q8P8J2
Uniprot Name
N-acetylornithine carbamoyltransferase
Molecular Weight
37872.96 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 06:10