NP-MRD: Showing NP-Card for N-Carbamyl-L-glutamic acid (NP0002717)

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Record Information

Version

2.0

Created at

2020-11-23 19:38:40 UTC

Updated at

2021-08-12 19:51:57 UTC

NP-MRD ID

NP0002717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Carbamyl-L-glutamic acid

Provided By

BMRB

Description

Carglumic acid, also known as carbaglu or acide carglumique, 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. Carglumic acid is a drug which is used for the treatment of acute and chronic hyperammonaemia in patients with n-acetylglutamate synthase (nags) deficiency. This enzyme is an important component of the urea cycle to prevent build up of neurotoxic ammonium in the blood. . Carglumic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. N-Carbamyl-L-glutamic acid was first documented in 2002 (PMID: 12447942). Based on a literature review a small amount of articles have been published on Carglumic acid (PMID: 15480384) (PMID: 20410539) (PMID: 21941437).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305052017392D          

 13 12  0  0  0  0            999 V2000
   -0.7183    1.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328    1.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7183   -0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    1.0371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7106    1.4497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.2121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    1.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395    1.4497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7183   -1.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039   -1.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7183    2.2747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328   -1.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  5  4  1  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  2  0  0  0  0
  4  3  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
  1 12  2  0  0  0  0
 10 13  1  0  0  0  0
  5  6  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0002717

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C6H10N2O5

> <MOLECULAR_WEIGHT>
190.154

> <EXACT_MASS>
190.05897144

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.78719144868495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(carbamoylamino)pentanedioic acid

> <ALOGPS_LOGP>
-1.06

> <JCHEM_LOGP>
-1.446560950333333

> <ALOGPS_LOGS>
-1.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.213080631300473

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.357865821959002

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2675959890994126

> <JCHEM_POLAR_SURFACE_AREA>
129.71999999999997

> <JCHEM_REFRACTIVITY>
39.40820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carglumic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAY-20         0                                  
HETATM    1  C   UNK     0      -1.341   2.706   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.675   1.936   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.341  -0.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.007   0.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.007   1.936   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.326   2.706   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       2.660   0.396   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.660   1.936   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.994   2.706   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.341  -1.914   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.007  -2.684   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.341   4.246   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.675  -2.684   0.000  0.00  0.00           O+0
CONECT    1    2    5   12                                                  
CONECT    2    1                                                            
CONECT    3    4   10                                                       
CONECT    4    5    3                                                       
CONECT    5    1    4    6                                                  
CONECT    6    8    5                                                       
CONECT    7    8                                                            
CONECT    8    6    9    7                                                  
CONECT    9    8                                                            
CONECT   10    3   11   13                                                  
CONECT   11   10                                                            
CONECT   12    1                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

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	MeSH, HMDB
N-Carbamoylglutamate	MeSH, HMDB

Chemical Formula

C₆H₁₀N₂O₅

Average Mass

190.1540 Da

Monoisotopic Mass

190.05897 Da

IUPAC Name

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

Traditional Name

carglumic acid

CAS Registry Number

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0015673

DrugBank ID

DB06775

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

108351

KEGG Compound ID

C05829

BioCyc ID

N-CARBAMYL-L-GLUTAMATE

BiGG ID

Not Available

Wikipedia Link

Carglumic_acid

METLIN ID

Not Available

PubChem Compound

121396

PDB ID

Not Available

ChEBI ID

71028

Good Scents ID

Not Available

References

General References

Elpeleg O, Shaag A, Ben-Shalom E, Schmid T, Bachmann C: N-acetylglutamate synthase deficiency and the treatment of hyperammonemic encephalopathy. Ann Neurol. 2002 Dec;52(6):845-9. doi: 10.1002/ana.10406. [PubMed:12447942 ]
Caldovic L, Morizono H, Daikhin Y, Nissim I, McCarter RJ, Yudkoff M, Tuchman M: Restoration of ureagenesis in N-acetylglutamate synthase deficiency by N-carbamylglutamate. J Pediatr. 2004 Oct;145(4):552-4. doi: 10.1016/j.jpeds.2004.06.047. [PubMed:15480384 ]
Thompson CA: Carglumic acid approved to treat genetic hyperammonemia. Am J Health Syst Pharm. 2010 May 1;67(9):690. doi: 10.2146/news100031. [PubMed:20410539 ]
Haberle J: Role of carglumic acid in the treatment of acute hyperammonemia due to N-acetylglutamate synthase deficiency. Ther Clin Risk Manag. 2011;7:327-32. doi: 10.2147/TCRM.S12703. Epub 2011 Aug 2. [PubMed:21941437 ]

Showing NP-Card for N-Carbamyl-L-glutamic acid (NP0002717)

MOL for NP0002717 (N-Carbamyl-L-glutamic acid)

3D MOL for NP0002717 (N-Carbamyl-L-glutamic acid)

3D SDF for NP0002717 (N-Carbamyl-L-glutamic acid)

3D-SDF for NP0002717 (N-Carbamyl-L-glutamic acid)

PDB for NP0002717 (N-Carbamyl-L-glutamic acid)

3D PDB for NP0002717 (N-Carbamyl-L-glutamic acid)

SMILES for NP0002717 (N-Carbamyl-L-glutamic acid)

INCHI for NP0002717 (N-Carbamyl-L-glutamic acid)

Structure for NP0002717 (N-Carbamyl-L-glutamic acid)

3D Structure for NP0002717 (N-Carbamyl-L-glutamic acid)