L-isoleucine (CHEBI:17191)

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CHEBI:17191 - L-isoleucine

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ChEBI Name	L-isoleucine

ChEBI ID	CHEBI:17191

ChEBI ASCII Name	L-isoleucine

Definition	The L-enantiomer of isoleucine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43290, CHEBI:43342, CHEBI:43366, CHEBI:6255, CHEBI:13127, CHEBI:21344

Supplier Information	ChemicalBook:CB2214184, eMolecules:508519, ZINC000008398603

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

ILE - Ideal conformer

RDKit 3D

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Time for openFile( ILE - Ideal conformer

RDKit 3D

22 21 0 0 0 0 0 0 0 0999 V2000

-1.9440 0.3350 -0.3430 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.4870 0.5190 -0.3690 C 0 0 2 0 0 0 0 0 0 0 0 0

0.0660 -0.0320 -1.6570 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4840 -0.9580 -2.2030 O 0 0 0 0 0 0 0 0 0 0 0 0

0.1400 -0.2190 0.8140 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.4210 0.3410 2.1220 C 0 0 0 0 0 0 0 0 0 0 0 0

1.6580 -0.0270 0.7880 C 0 0 0 0 0 0 0 0 0 0 0 0

0.2060 -0.3970 3.3050 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1710 0.5040 -2.1970 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.1120 -0.6560 -0.4100 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2560 0.6220 0.5720 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2530 1.5820 -0.2990 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0920 -1.2810 0.7440 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5020 0.2040 2.1410 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1880 1.4030 2.1920 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8910 1.0340 0.8570 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1050 -0.5540 1.6310 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0590 -0.4270 -0.1430 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1930 0.0010 4.2370 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0260 -1.4600 3.2350 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2870 -0.2610 3.2860 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5270 0.1500 -3.0240 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0

1 10 1 0

1 11 1 0

2 3 1 0

2 5 1 0

2 12 1 1

3 4 2 0

3 9 1 0

5 6 1 0

5 7 1 0

5 13 1 6

6 8 1 0

6 14 1 0

6 15 1 0

7 16 1 0

7 17 1 0

7 18 1 0

8 19 1 0

8 20 1 0

8 21 1 0

9 22 1 0

M END): 18 ms

reading 22 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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22 atoms created

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Wikipedia	License
Isoleucine (symbol Ile or I) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH+3 form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a hydrocarbon side chain with a branch (a central carbon atom bound to three other carbon atoms). It is classified as a non-polar, uncharged (at physiological pH), branched-chain, aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it. Essential amino acids are necessary in the human diet. In plants isoleucine can be synthesized from threonine and methionine. In plants and bacteria, isoleucine is synthesized from a pyruvate employing leucine biosynthesis enzymes. It is encoded by the codons AUU, AUC, and AUA.
Read full article at Wikipedia

Formulae

C6H13NO2
C6H13NO2

Net Charge

Average Mass

131.175

Monoisotopic Mass

131.09463

InChI

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1

InChIKey

AGPKZVBTJJNPAG-WHFBIAKZSA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. (via isoleucine )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-isoleucine (CHEBI:17191) has role Escherichia coli metabolite (CHEBI:76971) L-isoleucine (CHEBI:17191) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-isoleucine (CHEBI:17191) has role algal metabolite (CHEBI:84735) L-isoleucine (CHEBI:17191) has role human metabolite (CHEBI:77746) L-isoleucine (CHEBI:17191) has role mouse metabolite (CHEBI:75771) L-isoleucine (CHEBI:17191) has role plant metabolite (CHEBI:76924) L-isoleucine (CHEBI:17191) is a L-α-amino acid (CHEBI:15705) L-isoleucine (CHEBI:17191) is a aspartate family amino acid (CHEBI:22658) L-isoleucine (CHEBI:17191) is a isoleucine (CHEBI:24898) L-isoleucine (CHEBI:17191) is a proteinogenic amino acid (CHEBI:83813) L-isoleucine (CHEBI:17191) is conjugate acid of L-isoleucinate (CHEBI:32604) L-isoleucine (CHEBI:17191) is conjugate base of L-isoleucinium (CHEBI:32605) L-isoleucine (CHEBI:17191) is enantiomer of D-isoleucine (CHEBI:27730) L-isoleucine (CHEBI:17191) is tautomer of L-isoleucine zwitterion (CHEBI:58045)

Incoming	α-Asp-Ile (CHEBI:68599) has functional parent L-isoleucine (CHEBI:17191) (4S)-3¹,4-dihydroxy-L-isoleucine zwitterion (CHEBI:149628) has functional parent L-isoleucine (CHEBI:17191) L-isoleucine derivative (CHEBI:84111) has functional parent L-isoleucine (CHEBI:17191) Asn-Ile (CHEBI:141421) has functional parent L-isoleucine (CHEBI:17191) Asp-Lys-Ile (CHEBI:138791) has functional parent L-isoleucine (CHEBI:17191) DON-10-isoleucine (CHEBI:149454) has functional parent L-isoleucine (CHEBI:17191) Glu-Asp-Ile (CHEBI:73491) has functional parent L-isoleucine (CHEBI:17191) Glu-Glu-Ile (CHEBI:73492) has functional parent L-isoleucine (CHEBI:17191) Glu-Ile (CHEBI:141436) has functional parent L-isoleucine (CHEBI:17191) Glu-Ile-Phe (CHEBI:73497) has functional parent L-isoleucine (CHEBI:17191) Glu-Ile-Ser (CHEBI:73498) has functional parent L-isoleucine (CHEBI:17191) Glu-Ile-Val (CHEBI:73499) has functional parent L-isoleucine (CHEBI:17191) His-Ile (CHEBI:141437) has functional parent L-isoleucine (CHEBI:17191) Ile-Asp (CHEBI:141439) has functional parent L-isoleucine (CHEBI:17191) Ile-His (CHEBI:73520) has functional parent L-isoleucine (CHEBI:17191) Ile-Ile (CHEBI:74067) has functional parent L-isoleucine (CHEBI:17191) Ile-Leu-Trp-Trp (CHEBI:73518) has functional parent L-isoleucine (CHEBI:17191) Ile-Leu-Val-Tyr (CHEBI:73519) has functional parent L-isoleucine (CHEBI:17191) Ile-Lys (CHEBI:141440) has functional parent L-isoleucine (CHEBI:17191) Ile-Thr (CHEBI:141441) has functional parent L-isoleucine (CHEBI:17191) Pro-Glu-Ile (CHEBI:144613) has functional parent L-isoleucine (CHEBI:17191) Thr-Ile (CHEBI:141446) has functional parent L-isoleucine (CHEBI:17191) Trp-Ile (CHEBI:141448) has functional parent L-isoleucine (CHEBI:17191) Tyr-Ile-Leu (CHEBI:165121) has functional parent L-isoleucine (CHEBI:17191) L-isoleucinium (CHEBI:32605) is conjugate acid of L-isoleucine (CHEBI:17191) L-isoleucinate (CHEBI:32604) is conjugate base of L-isoleucine (CHEBI:17191) D-isoleucine (CHEBI:27730) is enantiomer of L-isoleucine (CHEBI:17191) L-isoleucine residue (CHEBI:30009) is substituent group from L-isoleucine (CHEBI:17191) L-isoleucino group (CHEBI:32607) is substituent group from L-isoleucine (CHEBI:17191) L-isoleucyl group (CHEBI:32606) is substituent group from L-isoleucine (CHEBI:17191) L-isoleucine zwitterion (CHEBI:58045) is tautomer of L-isoleucine (CHEBI:17191)

IUPAC Name

L-isoleucine

Synonyms	Sources
(2S,3S)-2-amino-3-methylpentanoic acid	IUPAC
2-Amino-3-methylvaleric acid	KEGG COMPOUND
α-amino-β-methylvaleric acid	NIST Chemistry WebBook
I	ChEBI
Ile	ChEBI
ISOLEUCINE	PDBeChem
L-Isoleucine	KEGG COMPOUND

Manual Xrefs	Databases
4129	DrugCentral
C00001374	KNApSAcK
C00407	KEGG COMPOUND
D00065	KEGG DRUG
DB00167	DrugBank
ECMDB00172	ECMDB
HMDB0000172	HMDB
ILE	PDBeChem
ILE	MetaCyc
Isoleucine	Wikipedia
YMDB00038	YMDB
View more database links

Registry Numbers	Types	Sources
1721792	Reaxys Registry Number	Reaxys
486381	Gmelin Registry Number	Gmelin
73-32-5	CAS Registry Number	KEGG COMPOUND
73-32-5	CAS Registry Number	NIST Chemistry WebBook
73-32-5	CAS Registry Number	ChemIDplus

Citations

Last Modified

08 April 2022

CHEBI:17191 - L-isoleucine

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