MiMeDB: Showing metabocard for D-Isoleucine (MMDBc0033161)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:37:11 UTC

Update Date

2025-10-07 16:04:17 UTC

Metabolite ID

MMDBc0033161

Metabolite Identification

Common Name

D-Isoleucine

Description

D-Isoleucine is a nonproteinogenic amino acid belonging to the class of amino acids. Its chemical structure features a branched-chain configuration, characterized by a unique Cβ-epimerization process that distinguishes it from its L-isomer counterpart, making it less common in natural peptides (PMID:31061373 ). D-Isoleucine participates in various biochemical pathways, including its role in diagnostic models where it is combined with other metabolites like d-serine and β-(pyrazol-1-yl)-l-alanine, achieving high predictive accuracy (PMID:34229439 ). It has also been utilized in the synthesis of chiral superatomic silver nanoclusters, showcasing its versatility in chemical applications (PMID:33629455 ). Additionally, D-isoleucine has been implicated in modulating neurotransmission, specifically in reducing glycinergic transmission and enhancing glycine release through hetero-exchange mechanisms (PMID:29867218 ). Furthermore, its selective assay capabilities allow for the differentiation of isoleucine isomers in complex mixtures (PMID:30123202 ). Notably, research indicates significant variations in serum concentrations of D-isoleucine and other amino acids in hepatocellular carcinoma patients compared to healthy individuals, highlighting its potential relevance in clinical chemistry (PMID:29492623 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3R)-2-Amino-3-methylpentanoic acid	ChEBI
(2R,3R)-2-Amino-3-methylvaleric acid	ChEBI
(R)-2-Amino-(S)-3-methylvaleric acid	ChEBI
DIL	ChEBI
(2R,3R)-2-Amino-3-methylpentanoate	Generator
(2R,3R)-2-Amino-3-methylvalerate	Generator
(R)-2-Amino-(S)-3-methylvalerate	Generator

Molecular Formula

C₆H₁₃NO₂

Average Mass

131.1729

Monoisotopic Mass

131.094628665

IUPAC Name

(2R,3R)-2-amino-3-methylpentanoic acid

Traditional Name

D-isoleucine

CAS Registry Number

319-78-8

SMILES

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

InChI Identifier

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m1/s1

InChI Key

AGPKZVBTJJNPAG-RFZPGFLSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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

Isoleucine and derivatives

Alternative Parents

Substituents

Isoleucine or derivatives
Alpha-amino acid
D-alpha-amino acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acid
Fatty acyl
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:27730 )
isoleucine (CHEBI:27730 )
Other amino acids (C06418 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	114 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.5	ChemAxon
logS	-0.06	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	9.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.09 m³·mol⁻¹	ChemAxon
Polarizability	14.05 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9100000000-40bc9ef43da5f18be883	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9500000000-00268b2694cde281641b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-4014793e17e0290790a4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-eb9a97a14461e524e76e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-ead56ef2118d09148965	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-5900000000-9335d1d91071c615ade6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-e7df49772ae8a5d6660c	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	414.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	317.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	159.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	277.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	305.5
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	326.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	692.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	549.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	551.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	192.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	393.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	181.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	74.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	252.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	490.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	59.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	238.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	778.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	663.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	D-Isoleucine_TMS_1	CC[C@@H](C)[C@@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1677.79
Gas Chromatography	D-Isoleucine_TMS_2	CC[C@@H](C)[C@@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1942.27
Gas Chromatography	D-Isoleucine_TMS_3	CC[C@@H](C)[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1924.66
Gas Chromatography	D-Isoleucine_TMS_4	CC[C@@H](C)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2072.95
Gas Chromatography	D-Isoleucine_TMS_5	CC[C@@H](C)[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1696.18
Gas Chromatography	D-Isoleucine_TMS_1	CC[C@@H](C)[C@@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2027.12
Gas Chromatography	D-Isoleucine_TMS_2	CC[C@@H](C)[C@@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2353.12
Gas Chromatography	D-Isoleucine_TMS_3	CC[C@@H](C)[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2168.91
Gas Chromatography	D-Isoleucine_TMS_4	CC[C@@H](C)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2227.99
Gas Chromatography	D-Isoleucine_TMS_5	CC[C@@H](C)[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2571.28

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06418

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoleucine

METLIN ID

Not Available

PubChem Compound

76551

PDB ID

Not Available

ChEBI ID

27730

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Scheer M, Grote A, Chang A, Schomburg I, Munaretto C, Rother M, Sohngen C, Stelzer M, Thiele J, Schomburg D: BRENDA, the enzyme information system in 2011. Nucleic Acids Res. 2011 Jan;39(Database issue):D670-6. doi: 10.1093/nar/gkq1089. Epub 2010 Nov 9. [PubMed:21062828 ]

Showing metabocard for D-Isoleucine (MMDBc0033161)

MOL for #<Metabolite:0x00007f9ac94c26e0>

3D MOL for #<Metabolite:0x00007f9ac94c26e0>

3D SDF for #<Metabolite:0x00007f9ac94c26e0>

3D-SDF for #<Metabolite:0x00007f9ac94c26e0>

PDB for #<Metabolite:0x00007f9ac94c26e0>

3D PDB for #<Metabolite:0x00007f9ac94c26e0>

SMILES for #<Metabolite:0x00007f9ac94c26e0>

INCHI for #<Metabolite:0x00007f9ac94c26e0>

Structure for #<Metabolite:0x00007f9ac94c26e0>

3D Structure for #<Metabolite:0x00007f9ac94c26e0>