Back to Compounds

Showing Compound L-Alloisoleucine (FDB022117)

Record Information
Version1.0
Creation date2011-09-21 00:08:44 UTC
Update date2019-11-26 03:21:01 UTC
Primary IDFDB022117
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Alloisoleucine
DescriptionL-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). 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. [HMDB]
CAS Number1509-34-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2S,3R)-2-Amino-3-methylpentanoic acidChEBI
AlleChEBI
Allo-L-isoleucineChEBI
L(+)-AlloisoleucineChEBI
Threo-3-methyl-L-norvalineChEBI
Threo-L-isoleucineChEBI
(2S,3R)-2-Amino-3-methylpentanoateGenerator
AlloisoleucineHMDB
IsoleucineHMDB
Isoleucine, L isomerHMDB
Isoleucine, L-isomerHMDB
L-IsoleucineHMDB
L-Isomer isoleucineHMDB
(3R)-LS-IsoleucineHMDB
2-Amino-3-methyl-[S-(r*,s*)]-pentanoateHMDB
2-Amino-3-methyl-[S-(r*,s*)]-pentanoic acidHMDB
Allo-isoleucineHMDB
L-Allo-isoleucineHMDB
[S-(R*,s*)]-2-amino-3-methylpentanoateHMDB
[S-(R*,s*)]-2-amino-3-methylpentanoic acidHMDB
(2S,3R)-2-amino-3-methylpentanoatehmdb
(2S,3R)-2-amino-3-methylpentanoic acidhmdb
[S-(R*,S*)]-2-Amino-3-methylpentanoatehmdb
[S-(R*,S*)]-2-Amino-3-methylpentanoic acidhmdb
2-amino-3-methyl-[S-(R*,S*)]-Pentanoatehmdb
2-amino-3-methyl-[S-(R*,S*)]-Pentanoic acidhmdb
Allo-Isoleucinehmdb
Allo-L-Isoleucinehmdb
L-allo-Isoleucinehmdb
L-alloisoleucinehmdb
threo-3-methyl-L-Norvalinehmdb
threo-L-Isoleucinehmdb
Predicted Properties
PropertyValueSource
Water Solubility114 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS-0.06ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.09 m³·mol⁻¹ChemAxon
Polarizability14.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H13NO2
IUPAC name(2S,3R)-2-amino-3-methylpentanoic acid
InChI IdentifierInChI=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 KeyAGPKZVBTJJNPAG-UHNVWZDZSA-N
Isomeric SMILESCC[C@@H](C)[C@H](N)C(O)=O
Average Molecular Weight131.1729
Monoisotopic Molecular Weight131.094628665
Classification
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentIsoleucine 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-Alloisoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00b9-9100000000-40bc9ef43da5f18be883Spectrum
Predicted GC-MSL-Alloisoleucine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9400000000-3a446aac1ca67e24d0d5Spectrum
Predicted GC-MSL-Alloisoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Alloisoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Alloisoleucine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Alloisoleucine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Alloisoleucine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-3900000000-703d0f350ebca58a7eb12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ko-9000000000-b7c643e18a4283fc88e42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9000000000-6b799d2abf4132bac9742012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000x-9700000000-fd99c6b1f756eda9c88a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-59856e2f5d49bcd1ddcc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a7cba7696438bbc753672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-3f3a1371dbb8cee999752021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-b869312a540376f316612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9300000000-cc3611bb367101c1f9e02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9100000000-f44a7527300b2ee92bd22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-bb99da9182449d9406052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-71d0a2db50a0c84ca4d42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9500000000-00268b2694cde281641b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-4014793e17e0290790a42017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-eb9a97a14461e524e76e2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-ead56ef2118d091489652017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5900000000-9335d1d91071c615ade62017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-e7df49772ae8a5d6660c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9100000000-6deeb9c0f6e2a54158ea2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-9000000000-4fcbf47ecbe7cea12b862021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-175f823a38c66789e1302021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-06466c9190b13de8e4be2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-06466c9190b13de8e4be2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05al-9500000000-8575fe92309b181021412021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID89698
ChEMBL IDCHEMBL56053
KEGG Compound IDNot Available
Pubchem Compound ID99288
Pubchem Substance IDNot Available
ChEBI ID22359
Phenol-Explorer IDNot Available
DrugBank IDDB01739
HMDB IDHMDB00557
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDIIL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference