NP-MRD: Showing NP-Card for Isovalerylalanine (NP0000588)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-16 18:04:07 UTC

NP-MRD ID

NP0000588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isovalerylalanine

Description

Isovalerylalanine, also known as isopentanoylalanine, 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. Isovalerylalanine results from the formal condensation of the carboxy group of isovaleric acid with the amino group of L-alanine. Isovalerylalanine is one of the constituents of the organic acid profile in isovaleric acidemia, it is believed to be formed by the action of the enzyme glycine N-acylase on alanine, using isovaleryl-CoA as a substrate (PMID: 6197208 ). Isovaleric acidemia was the first organic acid acidemia to be documented in humans. It is an autosomal recessive inborn error in the metabolism of leucine, caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD) that results in the accumulation isovaleryl-CoA derivatives (PMID: 16602101). The excess of isovaleryl-CoA in plasma allows for the formation of condensation derivatives, such as isovalerylalanine which makes it one of the biomarkers for this condition.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Isovalerylalanine.mol                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.080  -0.667   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.770   0.667   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.540  -0.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770  -2.001   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.850   0.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.850  -2.001   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.770   0.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.540   2.001   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.540  -0.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.080  -0.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.850  -2.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.850   0.667   0.000  0.00  0.00           C+0
CONECT    1    3    5    6                                                  
CONECT    2    3    7                                                       
CONECT    3    2    1    4                                                  
CONECT    4    3                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    8    9    2                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0000747
HETATM    1  C1  UNL     1      -2.980   1.081   0.419  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.632  -0.070  -0.457  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.522   0.393  -1.882  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.432  -0.850  -0.013  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.194  -0.080   0.059  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.083   1.140  -0.216  1.00  0.00           O  
HETATM    7  N1  UNL     1       0.988  -0.751   0.473  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.258  -0.059   0.571  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.754  -0.115   1.999  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.257  -0.609  -0.377  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.990  -1.553  -1.147  1.00  0.00           O  
HETATM   12  O3  UNL     1       4.526  -0.061  -0.414  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.353   1.982   0.260  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.041   0.794   1.492  1.00  0.00           H  
HETATM   15  H3  UNL     1      -4.024   1.403   0.147  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.502  -0.786  -0.425  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.810   1.453  -2.013  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.465   0.265  -2.222  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.188  -0.187  -2.577  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.277  -1.659  -0.777  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.613  -1.362   0.936  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.986  -1.780   0.724  1.00  0.00           H  
HETATM   23  H11 UNL     1       2.079   0.994   0.275  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.167   0.629   2.577  1.00  0.00           H  
HETATM   25  H13 UNL     1       2.533  -1.119   2.413  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.826   0.132   2.024  1.00  0.00           H  
HETATM   27  H15 UNL     1       4.751   0.779   0.106  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5   20   21
CONECT    5    6    6    7
CONECT    7    8   22
CONECT    8    9   10   23
CONECT    9   24   25   26
CONECT   10   11   11   12
CONECT   12   27
END

View in JSmol

Synonyms

Value	Source
(2S)-2-(3-Methylbutanamido)propanoic acid	ChEBI
Isopentanoylalanine	ChEBI
N-Isopentanoyl-L-alanine	ChEBI
N-Isopentanoylalanine	ChEBI
N-Isovalerylalanine	ChEBI
(2S)-2-(3-Methylbutanamido)propanoate	Generator
N-Isovaleryl-L-alanine	HMDB
Isovalerylalanine	ChEBI

Chemical Formula

C₈H₁₅NO₃

Average Mass

173.2096 Da

Monoisotopic Mass

173.10519 Da

IUPAC Name

(2S)-2-(3-methylbutanamido)propanoic acid

Traditional Name

isovalerylalanine

CAS Registry Number

68219-63-6

SMILES

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

InChI Identifier

InChI=1S/C8H15NO3/c1-5(2)4-7(10)9-6(3)8(11)12/h5-6H,4H2,1-3H3,(H,9,10)(H,11,12)/t6-/m0/s1

InChI Key

OJPSNARFDYTAEN-LURJTMIESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, 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

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

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
Alanine or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

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
Water Solubility	11 g/L	ALOGPS
logP	0.8	ALOGPS
logP	0.67	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.72 m³·mol⁻¹	ChemAxon
Polarizability	18.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000747

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022219

KNApSAcK ID

Not Available

Chemspider ID

114516

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5715

PubChem Compound

129285

PDB ID

Not Available

ChEBI ID

136818

Good Scents ID

Not Available

References

General References

Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208 ]

Showing NP-Card for Isovalerylalanine (NP0000588)

MOL for NP0000588 (Isovalerylalanine)

3D MOL for NP0000588 (Isovalerylalanine)

3D SDF for NP0000588 (Isovalerylalanine)

3D-SDF for NP0000588 (Isovalerylalanine)

PDB for NP0000588 (Isovalerylalanine)

3D PDB for NP0000588 (Isovalerylalanine)

SMILES for NP0000588 (Isovalerylalanine)

INCHI for NP0000588 (Isovalerylalanine)

Structure for NP0000588 (Isovalerylalanine)

3D Structure for NP0000588 (Isovalerylalanine)