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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

2021-09-10 23:23:21 UTC

Update Date

2021-09-26 22:55:24 UTC

HMDB ID

HMDB0246363

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Aminoquinoline

Description

1,4-dihydroquinolin-4-imine belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system. Based on a literature review very few articles have been published on 1,4-dihydroquinolin-4-imine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-aminoquinoline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-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 Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₈N₂

Average Molecular Weight

144.1732

Monoisotopic Molecular Weight

144.068748266

IUPAC Name

1,4-dihydroquinolin-4-imine

Traditional Name

4-aminoquinoline

CAS Registry Number

Not Available

SMILES

N=C1C=CNC2=CC=CC=C12

InChI Identifier

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

InChI Key

FQYRLEXKXQRZDH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

4-aminoquinolines

Alternative Parents

Substituents

4-aminoquinoline
Aminopyridine
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	0.88	ALOGPS
logP	1.31	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	15.6	ChemAxon
pKa (Strongest Basic)	12.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	35.88 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	57.49 m³·mol⁻¹	ChemAxon
Polarizability	15.32 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-2H]-	163.769	30932474
DeepCCS	[M+Na]+	139.078	30932474
AllCCS	[M+H]+	134.2	32859911
AllCCS	[M+H-H2O]+	129.7	32859911
AllCCS	[M+NH4]+	138.4	32859911
AllCCS	[M+Na]+	139.6	32859911
AllCCS	[M-H]-	127.6	32859911
AllCCS	[M+Na-2H]-	128.7	32859911
AllCCS	[M+HCOO]-	129.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.1768 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	972.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	70.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	161.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	244.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	239.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	443.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	592.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	64.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	637.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	555.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	354.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	182.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Aminoquinoline	N=C1C=CNC2=CC=CC=C12	2493.4	Standard polar	33892256
4-Aminoquinoline	N=C1C=CNC2=CC=CC=C12	1598.6	Standard non polar	33892256
4-Aminoquinoline	N=C1C=CNC2=CC=CC=C12	1750.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Aminoquinoline,1TMS,isomer #1	C[Si](C)(C)N=C1C=C[NH]C2=CC=CC=C12	1628.8	Semi standard non polar	33892256
4-Aminoquinoline,1TMS,isomer #1	C[Si](C)(C)N=C1C=C[NH]C2=CC=CC=C12	1655.1	Standard non polar	33892256
4-Aminoquinoline,1TMS,isomer #1	C[Si](C)(C)N=C1C=C[NH]C2=CC=CC=C12	2258.1	Standard polar	33892256
4-Aminoquinoline,1TMS,isomer #2	C[Si](C)(C)N1C=CC(=N)C2=CC=CC=C21	1817.3	Semi standard non polar	33892256
4-Aminoquinoline,1TMS,isomer #2	C[Si](C)(C)N1C=CC(=N)C2=CC=CC=C21	1763.4	Standard non polar	33892256
4-Aminoquinoline,1TMS,isomer #2	C[Si](C)(C)N1C=CC(=N)C2=CC=CC=C21	2178.4	Standard polar	33892256
4-Aminoquinoline,2TMS,isomer #1	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C2=CC=CC=C12	1811.9	Semi standard non polar	33892256
4-Aminoquinoline,2TMS,isomer #1	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C2=CC=CC=C12	1881.6	Standard non polar	33892256
4-Aminoquinoline,2TMS,isomer #1	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C2=CC=CC=C12	2029.6	Standard polar	33892256
4-Aminoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=C[NH]C2=CC=CC=C12	1885.4	Semi standard non polar	33892256
4-Aminoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=C[NH]C2=CC=CC=C12	1840.9	Standard non polar	33892256
4-Aminoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=C[NH]C2=CC=CC=C12	2370.6	Standard polar	33892256
4-Aminoquinoline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=CC(=N)C2=CC=CC=C21	2020.5	Semi standard non polar	33892256
4-Aminoquinoline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=CC(=N)C2=CC=CC=C21	1979.3	Standard non polar	33892256
4-Aminoquinoline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=CC(=N)C2=CC=CC=C21	2300.5	Standard polar	33892256
4-Aminoquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2213.3	Semi standard non polar	33892256
4-Aminoquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2272.2	Standard non polar	33892256
4-Aminoquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2263.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminoquinoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-0900000000-4e77c8621f37dfa268ca	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-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 - 4-Aminoquinoline 10V, Positive-QTOF	splash10-0002-0900000000-95bbe2b7dfc9b9638ba0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoquinoline 20V, Positive-QTOF	splash10-0002-0900000000-95bbe2b7dfc9b9638ba0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoquinoline 40V, Positive-QTOF	splash10-014i-9300000000-64ec60a7c6a8cb63cd2e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoquinoline 10V, Negative-QTOF	splash10-0006-0900000000-a43e340bb2a95a9ab2aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoquinoline 20V, Negative-QTOF	splash10-0006-0900000000-a43e340bb2a95a9ab2aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoquinoline 40V, Negative-QTOF	splash10-0006-1900000000-38df49176f54d9ff53c3	2021-10-12	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

61751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 4-Aminoquinoline (HMDB0246363)

MOL for HMDB0246363 (4-Aminoquinoline)

3D MOL for HMDB0246363 (4-Aminoquinoline)

3D SDF for HMDB0246363 (4-Aminoquinoline)

3D-SDF for HMDB0246363 (4-Aminoquinoline)

PDB for HMDB0246363 (4-Aminoquinoline)

3D PDB for HMDB0246363 (4-Aminoquinoline)

SMILES for HMDB0246363 (4-Aminoquinoline)

INCHI for HMDB0246363 (4-Aminoquinoline)

Structure for HMDB0246363 (4-Aminoquinoline)

3D Structure for HMDB0246363 (4-Aminoquinoline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra