ChemFOnt: Showing chemical card for Citrullin (CFc000333570)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:47 UTC

Chemfont ID

CFc000333570

Molecule Identification

Common Name

Citrullin

Definition

Citrullin, also known as cit or 2-amino-5-uredovaleric acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Citrullin is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Citrullin can be found in a number of food items such as cow milk, sesame, orange bell pepper, and pepper (c. frutescens), which makes citrullin a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-5-uredovaleric acid	ChEBI
Cit	ChEBI
Citrulina	ChEBI
DL-2-Amino-5-ureidovaleric acid	ChEBI
DL-Citrulline	ChEBI
N(5)-(Aminocarbonyl)-DL-ornithine	ChEBI
N(5)-(Aminocarbonyl)ornithine	ChEBI
N(5)-Carbamoyl-DL-ornithine	ChEBI
2-Amino-5-uredovalerate	Generator
DL-2-Amino-5-ureidovalerate	Generator

Chemical Formula

C₆H₁₃N₃O₃

Average Molecular Weight

175.1857

Monoisotopic Molecular Weight

175.095691297

IUPAC Name

2-amino-5-[(C-hydroxycarbonimidoyl)amino]pentanoic acid

Traditional Name

2-amino-5-(C-hydroxycarbonimidoylamino)pentanoic acid

CAS Registry Number

627-77-0

SMILES

NC(CCCNC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)

InChI Key

RHGKLRLOHDJJDR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Fatty acid
Carbonic acid derivative
Amino acid
Urea
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

citrullines (CHEBI:18211 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Herb and spice

Oilseed crop

Sesame (FooDB: FOOD00170)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Milk and milk product

Unfermented milk

Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	21.8 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-4.6	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Acidic)	0.012	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	52.27 m³·mol⁻¹	ChemAxon
Polarizability	17.48 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