MiMeDB: Showing metabocard for D-allo-isoleucine (MMDBc0055846)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:08:37 UTC

Update Date

2025-10-07 16:09:24 UTC

Metabolite ID

MMDBc0055846

Metabolite Identification

Common Name

D-allo-isoleucine

Description

D-allo-isoleucine is a branched-chain amino acid and a member of the amino acid chemical class. Its structure features a chiral center, distinguishing it from its L-isomer, and it plays a role in various metabolic pathways. D-allo-isoleucine is produced by certain lactic acid bacteria, such as Lactobacillus buchneri, which utilize isoleucine 2-epimerase to convert L-isoleucine into D-allo-isoleucine (PMID:28471367 ). This conversion involves the abstraction of the α-hydrogen and is crucial for the biosynthesis of other metabolites, including N-malonyl-D-allo-isoleucine (PMID:26324904 ). Additionally, D-allo-isoleucine is incorporated into bioactive peptides, such as bombinin H4, which exhibits antimicrobial properties (PMID:29337209 ). The synthesis of D-allo-isoleucine can increase the cost of certain biochemical processes, as noted in studies examining amino acid compositions (PMID:31015912 ). Furthermore, its production has been linked to the metabolic activities of various Lactobacillus species, highlighting its significance in microbial metabolism (PMID:30057575 ). Overall, D-allo-isoleucine serves as an important metabolite with diverse biochemical implications.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3S)-2-Amino-3-methylpentanoic acid	ChEBI
Allo-D-isoleucine	ChEBI
(2R,3S)-2-Amino-3-methylpentanoate	Generator

Molecular Formula

C₆H₁₃NO₂

Average Mass

131.175

Monoisotopic Mass

131.094628663

IUPAC Name

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

Traditional Name

Hile

CAS Registry Number

Not Available

SMILES

[H][C@](C)(CC)[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+/m0/s1

InChI Key

AGPKZVBTJJNPAG-CRCLSJGQSA-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:20899 )
alloisoleucine (CHEBI:20899 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-1.5	ChemAxon
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	14.23 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 (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	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	293.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	119.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	160.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	265.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	245.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	286.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	840.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	514.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	473.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	201.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	352.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	174.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	86.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	194.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	532.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	56.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	194.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	875.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	615.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	D-allo-isoleucine_TMS_1	CC[C@H](C)[C@@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1911.34
Gas Chromatography	D-allo-isoleucine_TMS_2	CC[C@H](C)[C@@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2282.22
Gas Chromatography	D-allo-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	2435.79
Gas Chromatography	D-allo-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	2072.11
Gas Chromatography	D-allo-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	2103.92
Gas Chromatography	D-allo-isoleucine_TMS_1	CC[C@H](C)[C@@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2225.94
Gas Chromatography	D-allo-isoleucine_TMS_2	CC[C@H](C)[C@@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2184.49
Gas Chromatography	D-allo-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	2576.14
Gas Chromatography	D-allo-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	2270.27
Gas Chromatography	D-allo-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	2624.39

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
Archaea/Archaea	Euryarchaeota	1
Bacteria/Eubacteria	Firmicutes	1	Human

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

85019

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94206

PDB ID

Not Available

ChEBI ID

20899

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for D-allo-isoleucine (MMDBc0055846)

MOL for #<Metabolite:0x00007f9aba70b0c8>

3D MOL for #<Metabolite:0x00007f9aba70b0c8>

3D SDF for #<Metabolite:0x00007f9aba70b0c8>

3D-SDF for #<Metabolite:0x00007f9aba70b0c8>

PDB for #<Metabolite:0x00007f9aba70b0c8>

3D PDB for #<Metabolite:0x00007f9aba70b0c8>

SMILES for #<Metabolite:0x00007f9aba70b0c8>

INCHI for #<Metabolite:0x00007f9aba70b0c8>

Structure for #<Metabolite:0x00007f9aba70b0c8>

3D Structure for #<Metabolite:0x00007f9aba70b0c8>