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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:25:39 UTC

Update Date

2021-09-26 22:57:06 UTC

HMDB ID

HMDB0247420

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Aminoquinoline

Description

8-Aminoquinoline, also known as sitamaquine or 8-quinolinamine, belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system. Based on a literature review a significant number of articles have been published on 8-Aminoquinoline. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-aminoquinoline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Aminoquinoline 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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Sitamaquine	HMDB
8-(6-Diethylaminohexylamino)-6-methoxy-4-methylquinoline dihydrochloride	HMDB
N,N-Diethyl-n'-(6-methoxy-4-methyl-8-quinolinyl)-1,6- hexanediamine	HMDB
8-((6-(Diethylamino)hexyl)amino)-6-methoxy-4-methylquinoline	HMDB
8-Quinolinamine	HMDB
Quinolin-8-ylamine	HMDB
Quinolin-8-amine	HMDB

Chemical Formula

C₉H₈N₂

Average Molecular Weight

144.1732

Monoisotopic Molecular Weight

144.068748266

IUPAC Name

quinolin-8-amine

Traditional Name

8-aminoquinoline

CAS Registry Number

Not Available

SMILES

NC1=CC=CC2=C1N=CC=C2

InChI Identifier

InChI=1S/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2

InChI Key

WREVVZMUNPAPOV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

Aminoquinolines and derivatives

Alternative Parents

Substituents

Aminoquinoline
Benzenoid
Pyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.51	ALOGPS
logP	1.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	19.95	ChemAxon
pKa (Strongest Basic)	4.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.91 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.68 m³·mol⁻¹	ChemAxon
Polarizability	15.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	128.757	30932474
DeepCCS	[M-H]-	125.605	30932474
DeepCCS	[M-2H]-	162.612	30932474
DeepCCS	[M+Na]+	137.807	30932474
AllCCS	[M+H]+	129.2	32859911
AllCCS	[M+H-H2O]+	124.3	32859911
AllCCS	[M+NH4]+	133.8	32859911
AllCCS	[M+Na]+	135.1	32859911
AllCCS	[M-H]-	128.0	32859911
AllCCS	[M+Na-2H]-	128.8	32859911
AllCCS	[M+HCOO]-	129.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Aminoquinoline	NC1=CC=CC2=C1N=CC=C2	2368.4	Standard polar	33892256
8-Aminoquinoline	NC1=CC=CC2=C1N=CC=C2	1525.8	Standard non polar	33892256
8-Aminoquinoline	NC1=CC=CC2=C1N=CC=C2	1528.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Aminoquinoline,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=CC=CN=C12	1642.8	Semi standard non polar	33892256
8-Aminoquinoline,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=CC=CN=C12	1675.9	Standard non polar	33892256
8-Aminoquinoline,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC2=CC=CN=C12	2256.6	Standard polar	33892256
8-Aminoquinoline,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC2=CC=CN=C12)[Si](C)(C)C	1708.5	Semi standard non polar	33892256
8-Aminoquinoline,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC2=CC=CN=C12)[Si](C)(C)C	1790.5	Standard non polar	33892256
8-Aminoquinoline,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC2=CC=CN=C12)[Si](C)(C)C	2084.3	Standard polar	33892256
8-Aminoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=CC=CN=C12	1906.8	Semi standard non polar	33892256
8-Aminoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=CC=CN=C12	1859.2	Standard non polar	33892256
8-Aminoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC2=CC=CN=C12	2419.4	Standard polar	33892256
8-Aminoquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC2=CC=CN=C12)[Si](C)(C)C(C)(C)C	2156.2	Semi standard non polar	33892256
8-Aminoquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC2=CC=CN=C12)[Si](C)(C)C(C)(C)C	2205.2	Standard non polar	33892256
8-Aminoquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC2=CC=CN=C12)[Si](C)(C)C(C)(C)C	2288.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Aminoquinoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0900000000-5261081b54cf0615f6c4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Aminoquinoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Aminoquinoline 10V, Positive-QTOF	splash10-0002-0900000000-95bbe2b7dfc9b9638ba0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Aminoquinoline 20V, Positive-QTOF	splash10-0002-0900000000-7762747ee6d678117dbc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Aminoquinoline 40V, Positive-QTOF	splash10-014l-9800000000-28696f93c52dcfcd5423	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Aminoquinoline 10V, Negative-QTOF	splash10-0006-0900000000-a43e340bb2a95a9ab2aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Aminoquinoline 20V, Negative-QTOF	splash10-0006-0900000000-d64d5228f973572d8a99	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Aminoquinoline 40V, Negative-QTOF	splash10-00kf-1900000000-bfff6bdaf1b85610f492	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

8-Aminoquinoline

METLIN ID

Not Available

PubChem Compound

11359

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for 8-Aminoquinoline (HMDB0247420)

MOL for HMDB0247420 (8-Aminoquinoline)

3D MOL for HMDB0247420 (8-Aminoquinoline)

3D SDF for HMDB0247420 (8-Aminoquinoline)

3D-SDF for HMDB0247420 (8-Aminoquinoline)

PDB for HMDB0247420 (8-Aminoquinoline)

3D PDB for HMDB0247420 (8-Aminoquinoline)

SMILES for HMDB0247420 (8-Aminoquinoline)

INCHI for HMDB0247420 (8-Aminoquinoline)

Structure for HMDB0247420 (8-Aminoquinoline)

3D Structure for HMDB0247420 (8-Aminoquinoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra