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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:45:51 UTC
Update Date2021-09-26 22:56:01 UTC
HMDB IDHMDB0246749
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Aminoindole
Description5-Aminoindole, also known as indol-5-ylamine, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Based on a literature review a significant number of articles have been published on 5-Aminoindole. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-aminoindole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Aminoindole is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
indol-5-YlamineChEBI
1-AminoindoleHMDB
7-AminoindoleHMDB
Chemical FormulaC8H8N2
Average Molecular Weight132.166
Monoisotopic Molecular Weight132.068748266
IUPAC Name1H-indol-5-amine
Traditional Name5-aminoindole
CAS Registry NumberNot Available
SMILES
NC1=CC2=C(NC=C2)C=C1
InChI Identifier
InChI=1S/C8H8N2/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H,9H2
InChI KeyZCBIFHNDZBSCEP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP1.55ALOGPS
logP1.24ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)17.39ChemAxon
pKa (Strongest Basic)3.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.81 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.84 m³·mol⁻¹ChemAxon
Polarizability14.3 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
DeepCCS[M+H]+126.77930932474
DeepCCS[M-H]-123.32430932474
DeepCCS[M-2H]-160.67430932474
DeepCCS[M+Na]+136.14230932474
AllCCS[M+H]+127.032859911
AllCCS[M+H-H2O]+122.132859911
AllCCS[M+NH4]+131.632859911
AllCCS[M+Na]+132.932859911
AllCCS[M-H]-124.732859911
AllCCS[M+Na-2H]-125.832859911
AllCCS[M+HCOO]-127.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-AminoindoleNC1=CC2=C(NC=C2)C=C12865.1Standard polar33892256
5-AminoindoleNC1=CC2=C(NC=C2)C=C11617.9Standard non polar33892256
5-AminoindoleNC1=CC2=C(NC=C2)C=C11631.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Aminoindole,1TMS,isomer #1C[Si](C)(C)NC1=CC=C2[NH]C=CC2=C11797.4Semi standard non polar33892256
5-Aminoindole,1TMS,isomer #1C[Si](C)(C)NC1=CC=C2[NH]C=CC2=C11790.2Standard non polar33892256
5-Aminoindole,1TMS,isomer #1C[Si](C)(C)NC1=CC=C2[NH]C=CC2=C12117.5Standard polar33892256
5-Aminoindole,1TMS,isomer #2C[Si](C)(C)N1C=CC2=CC(N)=CC=C211757.1Semi standard non polar33892256
5-Aminoindole,1TMS,isomer #2C[Si](C)(C)N1C=CC2=CC(N)=CC=C211762.1Standard non polar33892256
5-Aminoindole,1TMS,isomer #2C[Si](C)(C)N1C=CC2=CC(N)=CC=C212204.5Standard polar33892256
5-Aminoindole,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C2[NH]C=CC2=C1)[Si](C)(C)C1878.5Semi standard non polar33892256
5-Aminoindole,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C2[NH]C=CC2=C1)[Si](C)(C)C1914.4Standard non polar33892256
5-Aminoindole,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C2[NH]C=CC2=C1)[Si](C)(C)C2016.2Standard polar33892256
5-Aminoindole,2TMS,isomer #2C[Si](C)(C)NC1=CC=C2C(=C1)C=CN2[Si](C)(C)C1877.3Semi standard non polar33892256
5-Aminoindole,2TMS,isomer #2C[Si](C)(C)NC1=CC=C2C(=C1)C=CN2[Si](C)(C)C1912.7Standard non polar33892256
5-Aminoindole,2TMS,isomer #2C[Si](C)(C)NC1=CC=C2C(=C1)C=CN2[Si](C)(C)C1947.0Standard polar33892256
5-Aminoindole,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C2C(=C1)C=CN2[Si](C)(C)C)[Si](C)(C)C1896.5Semi standard non polar33892256
5-Aminoindole,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C2C(=C1)C=CN2[Si](C)(C)C)[Si](C)(C)C2005.2Standard non polar33892256
5-Aminoindole,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C2C(=C1)C=CN2[Si](C)(C)C)[Si](C)(C)C1890.7Standard polar33892256
5-Aminoindole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2[NH]C=CC2=C12039.6Semi standard non polar33892256
5-Aminoindole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2[NH]C=CC2=C11973.7Standard non polar33892256
5-Aminoindole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C2[NH]C=CC2=C12240.8Standard polar33892256
5-Aminoindole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=CC2=CC(N)=CC=C211996.9Semi standard non polar33892256
5-Aminoindole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=CC2=CC(N)=CC=C211952.4Standard non polar33892256
5-Aminoindole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=CC2=CC(N)=CC=C212307.8Standard polar33892256
5-Aminoindole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C2[NH]C=CC2=C1)[Si](C)(C)C(C)(C)C2336.5Semi standard non polar33892256
5-Aminoindole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C2[NH]C=CC2=C1)[Si](C)(C)C(C)(C)C2333.5Standard non polar33892256
5-Aminoindole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C2[NH]C=CC2=C1)[Si](C)(C)C(C)(C)C2186.6Standard polar33892256
5-Aminoindole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C2C(=C1)C=CN2[Si](C)(C)C(C)(C)C2328.7Semi standard non polar33892256
5-Aminoindole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C2C(=C1)C=CN2[Si](C)(C)C(C)(C)C2306.3Standard non polar33892256
5-Aminoindole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C2C(=C1)C=CN2[Si](C)(C)C(C)(C)C2164.6Standard polar33892256
5-Aminoindole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C2C(=C1)C=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2555.0Semi standard non polar33892256
5-Aminoindole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C2C(=C1)C=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2629.8Standard non polar33892256
5-Aminoindole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C2C(=C1)C=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2217.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Aminoindole GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-f4ab0c4f7d136ab792402021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Aminoindole 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 - 5-Aminoindole 10V, Positive-QTOFsplash10-001i-0900000000-ccaafacb3cf306c2544d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoindole 20V, Positive-QTOFsplash10-001i-0900000000-0c2414539f5b2bf5748f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoindole 40V, Positive-QTOFsplash10-0udi-5900000000-9fe68a8e01d1f8397ba72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoindole 10V, Negative-QTOFsplash10-001i-0900000000-546ff4527c4c3d89ff232021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoindole 20V, Negative-QTOFsplash10-001i-0900000000-546ff4527c4c3d89ff232021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Aminoindole 40V, Negative-QTOFsplash10-001i-2900000000-af46852511635d86a00a2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID71202
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78867
PDB IDNot Available
ChEBI ID33067
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]