ChemFOnt: Showing chemical card for Carglumic acid (CFc000009922)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:12 UTC

Chemfont ID

CFc000009922

Molecule Identification

Common Name

Carglumic acid

Definition

Carglumic acid is an orphan drug used for the treatment of hyperammonaemia in patients with N-acetylglutamate synthase deficiency. This rare genetic disorder results in elevated blood levels of ammonia, which can eventually cross the blood-brain barrier and cause neurologic problems, cerebral edema, coma, and death. Carglumic acid was approved by the U.S. Food and Drug Administration (FDA) on 18 March 2010.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-(Carbamoylamino)pentanedioic acid	ChEBI
Acide carglumique	ChEBI
Acido carglumico	ChEBI
Acidum carglumicum	ChEBI
Carbaglu	ChEBI
Carbamino-L-glutamic acid	ChEBI
Carbamylglutamic acid	ChEBI
L-N-Carbamoylglutamic acid	ChEBI
Ureidoglutaric acid	ChEBI
(2S)-2-(Carbamoylamino)pentanedioate	Generator
Carbamino-L-glutamate	Generator
Carbamylglutamate	Generator
L-N-Carbamoylglutamate	Generator
Ureidoglutarate	Generator
Carglumate	Generator
(S)-2-Ureidopentanedioic acid	HMDB
N-Carbamoyl-L-glutamic acid	HMDB
N-Carbamyl-L-glutamate	HMDB
N-Carbamylglutamate	HMDB
N-Carbamoyl-L-glutamate	HMDB
N-Carbamoylglutamate	HMDB

Chemical Formula

C₆H₁₀N₂O₅

Average Molecular Weight

190.154

Monoisotopic Molecular Weight

190.05897144

IUPAC Name

(2S)-2-(carbamoylamino)pentanedioic acid

Traditional Name

carglumic acid

CAS Registry Number

1188-38-1

SMILES

NC(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H10N2O5/c7-6(13)8-3(5(11)12)1-2-4(9)10/h3H,1-2H2,(H,9,10)(H,11,12)(H3,7,8,13)/t3-/m0/s1

InChI Key

LCQLHJZYVOQKHU-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Dicarboxylic acid or derivatives
Fatty acid
Isourea
Carboximidamide
Carboxylic acid
Carboximidic acid derivative
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organonitrogen compound
Imine
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ureas (CHEBI:71028 )
N-acyl-L-glutamic acid (CHEBI:71028 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)
Feces (PMID: 29808030)

Source

Exogenous

Exogenous (HMDB: HMDB0015673)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	19.1 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.4	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	39.41 m³·mol⁻¹	ChemAxon
Polarizability	16.79 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