Showing Compound N-acetyl-L-citrulline (FDB031018)

Record Information

Version

1.0

Creation date

2015-05-07 20:48:58 UTC

Update date

2019-11-26 03:22:04 UTC

Primary ID

FDB031018

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-acetyl-L-citrulline

Description

N-acetyl-l-citrulline, also known as (S)-2-acetamido-5-ureidopentanoic acid, is a member of the class of compounds known as N-acyl-l-alpha-amino acids. N-acyl-l-alpha-amino acids are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-acetyl-l-citrulline is slightly soluble (in water) and a weakly acidic compound (based on its pKa). N-acetyl-l-citrulline can be found in a number of food items such as macadamia nut, persian lime, broccoli, and annual wild rice, which makes N-acetyl-l-citrulline a potential biomarker for the consumption of these food products.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2S)-2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoate	Generator
(2S)-2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoic acid	ChEBI
(S)-2-ACETAMIDO-5-ureidopentanoate	Generator
(S)-2-ACETAMIDO-5-ureidopentanoIC ACID	ChEBI
alpha-N-Acetylcitrulline	HMDB
N-a-Acetyl-L-citrulline	Generator
N-Acetyl-L-citrulline	HMDB
N-Α-acetyl-L-citrulline	Generator
N2-Acetyl-N5-(aminocarbonyl)-L-ornithine	HMDB
Nalpha-acetyl-L-citrulline	HMDB

Showing 1 to 10 of 14 entries

Predicted Properties

Property	Value	Source
Water Solubility	3.57 g/L	ALOGPS
logP	-2	ALOGPS
logP	-1.9	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	50.77 m³·mol⁻¹	ChemAxon
Polarizability	21.49 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

Chemical Formula

C8H15N3O4

IUPAC name

(2S)-5-(carbamoylamino)-2-acetamidopentanoic acid

InChI Identifier

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

InChI Key

WMQMIOYQXNRROC-LURJTMIESA-N

Isomeric SMILES

CC(=O)N[C@@H](CCCNC(N)=O)C(O)=O

Average Molecular Weight

217.2224

Monoisotopic Molecular Weight

217.106255983

Classification

Description

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

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
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:49002 )
N-acetylcitrulline (CHEBI:49002 )

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	N-acetyl-L-citrulline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9400000000-7401e8328e755c9a54fe	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-acetyl-L-citrulline, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-0900000000-b7f7505693c52ea91fa5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900000000-a96ef51f6b478a3b6d30	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-9441d923bf5fa62ab976	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-7900000000-05a0d30dc4911b7ae9fc	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05xr-0930000000-3b9d796f05634936c485	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06w9-1900000000-ff1ced7b78fd0b206b4a	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5900000000-a4e2e243a03648720a7c	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xu-3920000000-b2b92b49a0c49064919f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05dl-4900000000-3deaf4d3cb14ff42b7e0	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-4bb42e23506bdcaba7c4	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-1940000000-d843dcf3f292d83e02a5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900000000-8ae141fbcff3973274ff	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-568f68b2bbb834a48941	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0490000000-c345f9ff031271a70e8c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0900-0910000000-6d0541054b5eb47b749e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9300000000-129aa9c775d01121bb1b	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound N-acetyl-L-citrulline (FDB031018)

Structure for FDB031018 (N-acetyl-L-citrulline)