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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:11:14 UTC
Update Date2023-02-21 17:17:52 UTC
HMDB IDHMDB0012992
Secondary Accession Numbers
  • HMDB12992
Metabolite Identification
Common NameLeukoaminochrome
DescriptionLeukoaminochrome, also known as 5,6-indolinediol or indoline-5,6-diol, belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. Leukoaminochrome is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Leukoaminochrome.
Structure
Data?1676999872
Synonyms
ValueSource
2,3-Dihydro-5,6-dihydroxyindoleChEBI
2-Descarboxy-cyclo-dopaChEBI
5,6-Dihydroxy-2,3-dihydroindoleChEBI
5,6-DihydroxyindolineChEBI
5,6-IndolinediolChEBI
56DHInnChEBI
Indoline-5,6-diolChEBI
LeucoaminochromeHMDB
Chemical FormulaC8H9NO2
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
IUPAC Name2,3-dihydro-1H-indole-5,6-diol
Traditional Name2,3-dihydro-1H-indole-5,6-diol
CAS Registry Number29539-03-5
SMILES
OC1=C(O)C=C2NCCC2=C1
InChI Identifier
InChI=1S/C8H9NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h3-4,9-11H,1-2H2
InChI KeyVGSVNUGKHOVSPK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
Alternative Parents
Substituents
  • Dihydroindole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility17270 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility17.5 g/LALOGPS
logP1.36ALOGPS
logP0.88ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)5.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.52 m³·mol⁻¹ChemAxon
Polarizability15.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.92931661259
DarkChem[M-H]-127.51531661259
DeepCCS[M+H]+135.58530932474
DeepCCS[M-H]-132.58130932474
DeepCCS[M-2H]-169.29530932474
DeepCCS[M+Na]+144.83230932474
AllCCS[M+H]+131.732859911
AllCCS[M+H-H2O]+127.032859911
AllCCS[M+NH4]+136.132859911
AllCCS[M+Na]+137.332859911
AllCCS[M-H]-129.232859911
AllCCS[M+Na-2H]-130.132859911
AllCCS[M+HCOO]-131.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LeukoaminochromeOC1=C(O)C=C2NCCC2=C12971.9Standard polar33892256
LeukoaminochromeOC1=C(O)C=C2NCCC2=C11681.9Standard non polar33892256
LeukoaminochromeOC1=C(O)C=C2NCCC2=C11724.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Leukoaminochrome,1TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O)NCC21741.0Semi standard non polar33892256
Leukoaminochrome,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)CCN21755.4Semi standard non polar33892256
Leukoaminochrome,1TMS,isomer #3C[Si](C)(C)N1CCC2=CC(O)=C(O)C=C211883.9Semi standard non polar33892256
Leukoaminochrome,2TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)NCC21828.5Semi standard non polar33892256
Leukoaminochrome,2TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C)CC21844.9Semi standard non polar33892256
Leukoaminochrome,2TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C=C1O)CCN2[Si](C)(C)C1856.3Semi standard non polar33892256
Leukoaminochrome,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)CC21890.8Semi standard non polar33892256
Leukoaminochrome,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)CC21883.9Standard non polar33892256
Leukoaminochrome,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)CC21875.4Standard polar33892256
Leukoaminochrome,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)NCC21985.6Semi standard non polar33892256
Leukoaminochrome,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN22004.8Semi standard non polar33892256
Leukoaminochrome,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1CCC2=CC(O)=C(O)C=C212140.5Semi standard non polar33892256
Leukoaminochrome,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)NCC22274.2Semi standard non polar33892256
Leukoaminochrome,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)CC22333.6Semi standard non polar33892256
Leukoaminochrome,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN2[Si](C)(C)C(C)(C)C2344.7Semi standard non polar33892256
Leukoaminochrome,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)CC22577.5Semi standard non polar33892256
Leukoaminochrome,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)CC22584.2Standard non polar33892256
Leukoaminochrome,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)CC22304.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Leukoaminochrome GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zmi-1900000000-25d2fbb7f811650a35c72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leukoaminochrome GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3190000000-f73a6d6c9c928f94d40a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leukoaminochrome GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 10V, Positive-QTOFsplash10-0udi-0900000000-ea5804ebafd462b893d52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 20V, Positive-QTOFsplash10-0udi-0900000000-8aa2be80a64f5c67626f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 40V, Positive-QTOFsplash10-0pdm-9500000000-d533de78e8b5c0754db62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 10V, Negative-QTOFsplash10-0udi-0900000000-ff9a5c5e15b09c7c5a612017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 20V, Negative-QTOFsplash10-0udi-0900000000-e7919fac3cd446c9d90d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 40V, Negative-QTOFsplash10-000x-9800000000-34dc5d16e4f5b51409002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 10V, Positive-QTOFsplash10-0udi-0900000000-00ad05f28905520632a92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 20V, Positive-QTOFsplash10-0udi-0900000000-a2c8811c0ab106aea8d42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 40V, Positive-QTOFsplash10-0006-9400000000-3226ed5ce190d34234142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 10V, Negative-QTOFsplash10-0udi-0900000000-c294e68376c4342ea7852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 20V, Negative-QTOFsplash10-0udi-1900000000-a93220e742bef664f0562021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukoaminochrome 40V, Negative-QTOFsplash10-0007-8900000000-3468369d6ceabb8d2c2c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029236
KNApSAcK IDNot Available
Chemspider ID129893
KEGG Compound IDC17756
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound147311
PDB IDNot Available
ChEBI ID74683
Food Biomarker OntologyNot Available
VMH IDCE5665
MarkerDB IDNot Available
Good Scents IDrw1727211
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available