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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:56 UTC

HMDB ID

HMDB0000557

Secondary Accession Numbers

HMDB0002291
HMDB00557
HMDB02291

Metabolite Identification

Common Name

L-Alloisoleucine

Description

L-alloisoleucine is a branched chain amino acid and is a stereo-isomer of L-isoleucine. It is a common constituent of human plasma (albeit at low levels). L-alloisoleucine is produced as a byproduct of isoleucine transamination. L-Isoleucine is one of the four common amino acids (the 3 others being threonine, hydroxyproline, and hydroxylysine) that have two asymmetric carbon atoms which produce four structural possibilities for the same chemical composition. L-alloisoleucine differs from L-isoleucine by having having different stereochemistry around its beta carbon. Plasma L-alloisoleucine, which is derived from L-isoleucine in vivo, can be used for the diagnosis of maple syrup urine disease (MSUD), a genetic disorder. Indeed, plasma L-alloisoleucine levels above 5 umol/L is the most specific and most sensitive diagnostic marker for all forms of MSUD (PMID: 10508118 ). In MSUD the degradation of the essential branched-chain L-amino acids leucine, valine, and isoleucine and their derived 2-oxoacids is impaired because of an inherited deficiency in branched-chain 2-oxoacid dehydrogenase complex (EC 1.2.4.4) activity. The accumulation of branched-chain compounds in blood and other body fluids can exert neurotoxic effects.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S,3R)-2-Amino-3-methylpentanoic acid	ChEBI
Alle	ChEBI
Allo-L-isoleucine	ChEBI
L(+)-Alloisoleucine	ChEBI
Threo-3-methyl-L-norvaline	ChEBI
Threo-L-isoleucine	ChEBI
(2S,3R)-2-Amino-3-methylpentanoate	Generator
Alloisoleucine	HMDB
Isoleucine	HMDB
Isoleucine, L isomer	HMDB
Isoleucine, L-isomer	HMDB
L-Isoleucine	HMDB
L-Isomer isoleucine	HMDB
(3R)-LS-Isoleucine	HMDB
2-Amino-3-methyl-[S-(r,s)]-pentanoate	HMDB
2-Amino-3-methyl-[S-(r,s)]-pentanoic acid	HMDB
Allo-isoleucine	HMDB
L-Allo-isoleucine	HMDB
[S-(R,s)]-2-amino-3-methylpentanoate	HMDB
[S-(R,s)]-2-amino-3-methylpentanoic acid	HMDB

Chemical Formula

C₆H₁₃NO₂

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

IUPAC Name

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

Traditional Name

allo-isoleucine

CAS Registry Number

1509-34-8

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-UHNVWZDZSA-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
L-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

non-proteinogenic L-alpha-amino acid (CHEBI:43433 )
alloisoleucine (CHEBI:43433 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000557)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000557)
Cerebrospinal fluid (HMDB: HMDB0000557)
Cerebrospinal Fluid (CSF) (HMDB: HMDB0000557)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0000557)
Urine (HMDB: HMDB0000557)

Source

Endogenous

Endogenous (HMDB: HMDB0000557)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000557)

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000187)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60 - 64 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	34.4 mg/mL at 25 °C	Not Available
LogP	-1.70	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	134.452	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001745

Predicted Molecular 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	14.23 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.076	31661259
DarkChem	[M-H]-	125.357	31661259
AllCCS	[M+H]+	132.342	32859911
AllCCS	[M-H]-	129.058	32859911
DeepCCS	[M+H]+	130.983	30932474
DeepCCS	[M-H]-	127.156	30932474
DeepCCS	[M-2H]-	164.493	30932474
DeepCCS	[M+Na]+	140.031	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	136.2	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	129.1	32859911
AllCCS	[M+Na-2H]-	131.9	32859911
AllCCS	[M+HCOO]-	135.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Alloisoleucine	CC[C@@H](C)[C@H](N)C(O)=O	1985.0	Standard polar	33892256
L-Alloisoleucine	CC[C@@H](C)[C@H](N)C(O)=O	1164.3	Standard non polar	33892256
L-Alloisoleucine	CC[C@@H](C)[C@H](N)C(O)=O	1292.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Alloisoleucine,1TMS,isomer #1	CC[C@@H](C)[C@H](N)C(=O)O[Si](C)(C)C	1180.4	Semi standard non polar	33892256
L-Alloisoleucine,1TMS,isomer #2	CC[C@@H](C)[C@H](N[Si](C)(C)C)C(=O)O	1292.1	Semi standard non polar	33892256
L-Alloisoleucine,2TMS,isomer #1	CC[C@@H](C)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1316.6	Semi standard non polar	33892256
L-Alloisoleucine,2TMS,isomer #1	CC[C@@H](C)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1308.4	Standard non polar	33892256
L-Alloisoleucine,2TMS,isomer #1	CC[C@@H](C)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1419.5	Standard polar	33892256
L-Alloisoleucine,2TMS,isomer #2	CC[C@@H](C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1480.8	Semi standard non polar	33892256
L-Alloisoleucine,2TMS,isomer #2	CC[C@@H](C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1322.9	Standard non polar	33892256
L-Alloisoleucine,2TMS,isomer #2	CC[C@@H](C)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1511.7	Standard polar	33892256
L-Alloisoleucine,3TMS,isomer #1	CC[C@@H](C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1501.3	Semi standard non polar	33892256
L-Alloisoleucine,3TMS,isomer #1	CC[C@@H](C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1434.9	Standard non polar	33892256
L-Alloisoleucine,3TMS,isomer #1	CC[C@@H](C)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1401.2	Standard polar	33892256
L-Alloisoleucine,1TBDMS,isomer #1	CC[C@@H](C)[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1396.9	Semi standard non polar	33892256
L-Alloisoleucine,1TBDMS,isomer #2	CC[C@@H](C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	1519.3	Semi standard non polar	33892256
L-Alloisoleucine,2TBDMS,isomer #1	CC[C@@H](C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1749.9	Semi standard non polar	33892256
L-Alloisoleucine,2TBDMS,isomer #1	CC[C@@H](C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1724.7	Standard non polar	33892256
L-Alloisoleucine,2TBDMS,isomer #1	CC[C@@H](C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1722.9	Standard polar	33892256
L-Alloisoleucine,2TBDMS,isomer #2	CC[C@@H](C)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1878.2	Semi standard non polar	33892256
L-Alloisoleucine,2TBDMS,isomer #2	CC[C@@H](C)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1758.8	Standard non polar	33892256
L-Alloisoleucine,2TBDMS,isomer #2	CC[C@@H](C)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1750.4	Standard polar	33892256
L-Alloisoleucine,3TBDMS,isomer #1	CC[C@@H](C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2161.4	Semi standard non polar	33892256
L-Alloisoleucine,3TBDMS,isomer #1	CC[C@@H](C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2055.1	Standard non polar	33892256
L-Alloisoleucine,3TBDMS,isomer #1	CC[C@@H](C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1828.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alloisoleucine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9100000000-40bc9ef43da5f18be883	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alloisoleucine GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9400000000-3a446aac1ca67e24d0d5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alloisoleucine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alloisoleucine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alloisoleucine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alloisoleucine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alloisoleucine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-3900000000-703d0f350ebca58a7eb1	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00ko-9000000000-b7c643e18a4283fc88e4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-052f-9000000000-6b799d2abf4132bac974	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 10V, Positive-QTOF	splash10-000x-9700000000-fd99c6b1f756eda9c88a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 20V, Positive-QTOF	splash10-0006-9100000000-59856e2f5d49bcd1ddcc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 40V, Positive-QTOF	splash10-0006-9000000000-a7cba7696438bbc75367	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 40V, Positive-QTOF	splash10-0a4i-9000000000-3f3a1371dbb8cee99975	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 20V, Negative-QTOF	splash10-0002-9000000000-b869312a540376f31661	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 40V, Negative-QTOF	splash10-03dl-9300000000-cc3611bb367101c1f9e0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 10V, Positive-QTOF	splash10-0a4i-9100000000-f44a7527300b2ee92bd2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 20V, Positive-QTOF	splash10-0a4i-9000000000-bb99da9182449d940605	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Alloisoleucine 10V, Negative-QTOF	splash10-001i-1900000000-71d0a2db50a0c84ca4d4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 10V, Positive-QTOF	splash10-0019-9500000000-00268b2694cde281641b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 20V, Positive-QTOF	splash10-000i-9000000000-4014793e17e0290790a4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 40V, Positive-QTOF	splash10-0a4i-9000000000-eb9a97a14461e524e76e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 10V, Negative-QTOF	splash10-001i-2900000000-ead56ef2118d09148965	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 20V, Negative-QTOF	splash10-001i-5900000000-9335d1d91071c615ade6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 40V, Negative-QTOF	splash10-0ab9-9000000000-e7df49772ae8a5d6660c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 10V, Positive-QTOF	splash10-000i-9100000000-6deeb9c0f6e2a54158ea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 20V, Positive-QTOF	splash10-014r-9000000000-4fcbf47ecbe7cea12b86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 40V, Positive-QTOF	splash10-0a4i-9000000000-175f823a38c66789e130	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 10V, Negative-QTOF	splash10-001i-0900000000-06466c9190b13de8e4be	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 20V, Negative-QTOF	splash10-001i-0900000000-06466c9190b13de8e4be	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Alloisoleucine 40V, Negative-QTOF	splash10-05al-9500000000-8575fe92309b18102141	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0-4 uM	Newborn (0-30 days old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	0-4 uM	Infant (1 - 3 months old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	0-4 uM	Children (3 months - 6 years old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	0-4 uM	Children (6 - 18 years old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	<2.100 uM	Newborn (0-30 days old)	Not Specified	Normal	15615815	details
Blood	Detected and Quantified	1.9 +/- 0.6 uM	Adult (>18 years old)	Both	Normal	15615815 10508118	details
Blood	Detected and Quantified	1.6 +/- 0.4 uM	Children (1-13 years old)	Both	Normal	10508118	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0-0.5 uM	Children (0 - 10 years old)	Both	Normal	BC Children's Hos...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0-0.5 uM	Adolescent (>11 years old)	Both	Normal	BC Children's Hos...	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	26709303	details
Urine	Detected and Quantified	<0.90 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<0.90 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<0.79 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<3.28 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<1.13 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	0 - 0.11 umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 0.11 umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 0.23 umol/mmol creatinine	Children (1 - 2 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 0.23 umol/mmol creatinine	Children (2 - 4 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 0.23 umol/mmol creatinine	Children (4 - 13 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 0.23 umol/mmol creatinine	Adolescent (13 - 21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 0.68 umol/mmol creatinine	Adult (>21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	<0.90 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	25.6 +/- 14.0 uM	Children (1 - 13 years old)	Not Specified	Maple syrup urine disease	18088602	details
Blood	Detected and Quantified	127 +/- 1 uM	Children (1-13 years old)	Both	Maple syrup urine disease (MSUD)	10508118	details
Blood	Detected and Quantified	1.500-2.600 uM	Newborn (0-30 days old)	Not Specified	2-Methylbutyryl-CoA dehydrogenase deficiency (SBACDD)	15615815	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	1.524 +/- 0.425 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Maple syrup urine disease
Schadewaldt P, Bodner-Leidecker A, Hammen HW, Wendel U: Significance of L-alloisoleucine in plasma for diagnosis of maple syrup urine disease. Clin Chem. 1999 Oct;45(10):1734-40. [PubMed:10508118 ] Barschak AG, Marchesan C, Sitta A, Deon M, Giugliani R, Wajner M, Vargas CR: Maple syrup urine disease in treated patients: biochemical and oxidative stress profiles. Clin Biochem. 2008 Mar;41(4-5):317-24. Epub 2007 Dec 5. [PubMed:18088602 ]
Short/branched chain acyl-CoA dehydrogenase deficiency
Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22. [PubMed:15615815 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

248600 (Maple syrup urine disease)
610006 (Short/branched chain acyl-CoA dehydrogenase deficiency)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB01739

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022117

KNApSAcK ID

Not Available

Chemspider ID

89698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99288

PDB ID

Not Available

ChEBI ID

43433

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000187

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22. [PubMed:15615815 ]
Schadewaldt P, Bodner-Leidecker A, Hammen HW, Wendel U: Significance of L-alloisoleucine in plasma for diagnosis of maple syrup urine disease. Clin Chem. 1999 Oct;45(10):1734-40. [PubMed:10508118 ]

Showing metabocard for L-Alloisoleucine (HMDB0000557)

MOL for HMDB0000557 (L-Alloisoleucine)

3D MOL for HMDB0000557 (L-Alloisoleucine)

3D SDF for HMDB0000557 (L-Alloisoleucine)

3D-SDF for HMDB0000557 (L-Alloisoleucine)

PDB for HMDB0000557 (L-Alloisoleucine)

3D PDB for HMDB0000557 (L-Alloisoleucine)

SMILES for HMDB0000557 (L-Alloisoleucine)

INCHI for HMDB0000557 (L-Alloisoleucine)

Structure for HMDB0000557 (L-Alloisoleucine)

3D Structure for HMDB0000557 (L-Alloisoleucine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra