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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-24 12:35:21 UTC
Update Date2022-09-22 18:35:00 UTC
HMDB IDHMDB0304810
Secondary Accession NumbersNone
Metabolite Identification
Common NamePro-Ile
DescriptionPro-Ile, also known as L-pro-L-ile or PI, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Pro-Ile is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Pro-Ile.
Structure
Thumb
Synonyms
ValueSource
L-Pro-L-ileChEBI
N-L-Prolyl-L-isoleucineChEBI
PIChEBI
ProlylisoleucineChEBI
Chemical FormulaC11H20N2O3
Average Molecular Weight228.292
Monoisotopic Molecular Weight228.147392512
IUPAC Name(2S,3S)-2-({hydroxy[(2S)-pyrrolidin-2-yl]methylidene}amino)-3-methylpentanoic acid
Traditional Name(2S,3S)-2-{[hydroxy((2S)-pyrrolidin-2-yl)methylidene]amino}-3-methylpentanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](C)(CC)[C@]([H])(N=C(O)[C@]1([H])CCCN1)C(O)=O
InChI Identifier
InChI=1S/C11H20N2O3/c1-3-7(2)9(11(15)16)13-10(14)8-5-4-6-12-8/h7-9,12H,3-6H2,1-2H3,(H,13,14)(H,15,16)/t7-,8-,9-/m0/s1
InChI KeyOCYROESYHWUPBP-CIUDSAMLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Valine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty amide
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.67ALOGPS
logP-1.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)9.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.48 m³·mol⁻¹ChemAxon
Polarizability24.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+153.5132859911
AllCCS[M+H-H2O]+150.01832859911
AllCCS[M+Na]+157.68332859911
AllCCS[M+NH4]+156.75132859911
AllCCS[M-H]-154.24232859911
AllCCS[M+Na-2H]-154.89732859911
AllCCS[M+HCOO]-155.71232859911
DeepCCS[M+H]+152.97530932474
DeepCCS[M-H]-150.61630932474
DeepCCS[M-2H]-184.2630932474
DeepCCS[M+Na]+159.40630932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pro-Ile,3TMS,isomer #1CC[C@H](C)[C@H](N=C(O[Si](C)(C)C)[C@@H]1CCCN1[Si](C)(C)C)C(=O)O[Si](C)(C)C1941.0Semi standard non polar33892256
Pro-Ile,3TMS,isomer #1CC[C@H](C)[C@H](N=C(O[Si](C)(C)C)[C@@H]1CCCN1[Si](C)(C)C)C(=O)O[Si](C)(C)C1968.9Standard non polar33892256
Pro-Ile,3TMS,isomer #1CC[C@H](C)[C@H](N=C(O[Si](C)(C)C)[C@@H]1CCCN1[Si](C)(C)C)C(=O)O[Si](C)(C)C2410.8Standard polar33892256
Pro-Ile,3TBDMS,isomer #1CC[C@H](C)[C@H](N=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2579.1Semi standard non polar33892256
Pro-Ile,3TBDMS,isomer #1CC[C@H](C)[C@H](N=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2456.9Standard non polar33892256
Pro-Ile,3TBDMS,isomer #1CC[C@H](C)[C@H](N=C(O[Si](C)(C)C(C)(C)C)[C@@H]1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2716.2Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 10V, Positive-QTOFsplash10-003r-4790000000-921116c2f011f773b3712019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 20V, Positive-QTOFsplash10-0089-9200000000-11d9d4d193dfbbd382fb2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 40V, Positive-QTOFsplash10-05fu-9000000000-480a0109a007535620432019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 10V, Negative-QTOFsplash10-0059-0490000000-799a7ee9e975120be3f22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 20V, Negative-QTOFsplash10-003r-4950000000-90041945068d2cf98e342019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 40V, Negative-QTOFsplash10-059x-9300000000-60275b631c4af791a5352019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 10V, Positive-QTOFsplash10-00b9-7390000000-3752891ff25c3c979fe32021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 20V, Positive-QTOFsplash10-00e9-9220000000-198dd0d7cc42d32a4bbc2021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 40V, Positive-QTOFsplash10-00dj-9000000000-f7e9a3bd76decbd0f54e2021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 10V, Negative-QTOFsplash10-0002-9170000000-b8260505dee7a865aee92021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 20V, Negative-QTOFsplash10-0002-9300000000-d92acf010de122c491862021-10-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pro-Ile 40V, Negative-QTOFsplash10-00ke-9200000000-2dc89e1e45dd1126c31a2021-10-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB098399
KNApSAcK IDNot Available
Chemspider ID5430866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID74790
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available