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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:15:07 UTC

Update Date

2021-09-26 22:56:48 UTC

HMDB ID

HMDB0247242

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Amino-7-chloroquinoline

Description

7-chloroquinolin-4-amine 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 a significant number of articles have been published on 7-chloroquinolin-4-amine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-amino-7-chloroquinoline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Amino-7-chloroquinoline 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

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       0.000  -3.080   0.000  0.00  0.00          Cl+0
HETATM   12  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10                                                            
CONECT   12    4                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Chloro-4-aminoquinoline	MeSH

Chemical Formula

C₉H₇ClN₂

Average Molecular Weight

178.62

Monoisotopic Molecular Weight

178.0297759

IUPAC Name

7-chloroquinolin-4-amine

Traditional Name

7-chloroquinolin-4-amine

CAS Registry Number

Not Available

SMILES

NC1=C2C=CC(Cl)=CC2=NC=C1

InChI Identifier

InChI=1S/C9H7ClN2/c10-6-1-2-7-8(11)3-4-12-9(7)5-6/h1-5H,(H2,11,12)

InChI Key

NDRZSRWMMUGOBP-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

Chloroquinoline
4-aminoquinoline
Haloquinoline
Aminopyridine
Aryl chloride
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Azacycle
Amine
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Non-excretory biofluid

Blood (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	2.24	ALOGPS
logP	1.91	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	7.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.91 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	49.48 m³·mol⁻¹	ChemAxon
Polarizability	17.67 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]+	136.215	30932474
DeepCCS	[M-H]-	133.386	30932474
DeepCCS	[M-2H]-	169.591	30932474
DeepCCS	[M+Na]+	145.025	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.9	32859911
AllCCS	[M+Na]+	145.0	32859911
AllCCS	[M-H]-	133.0	32859911
AllCCS	[M+Na-2H]-	133.8	32859911
AllCCS	[M+HCOO]-	134.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-7-chloroquinoline	NC1=C2C=CC(Cl)=CC2=NC=C1	2680.1	Standard polar	33892256
4-Amino-7-chloroquinoline	NC1=C2C=CC(Cl)=CC2=NC=C1	1859.1	Standard non polar	33892256
4-Amino-7-chloroquinoline	NC1=C2C=CC(Cl)=CC2=NC=C1	1913.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-7-chloroquinoline,1TMS,isomer #1	C[Si](C)(C)NC1=CC=NC2=CC(Cl)=CC=C12	1944.8	Semi standard non polar	33892256
4-Amino-7-chloroquinoline,1TMS,isomer #1	C[Si](C)(C)NC1=CC=NC2=CC(Cl)=CC=C12	1836.7	Standard non polar	33892256
4-Amino-7-chloroquinoline,1TMS,isomer #1	C[Si](C)(C)NC1=CC=NC2=CC(Cl)=CC=C12	2383.0	Standard polar	33892256
4-Amino-7-chloroquinoline,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	1933.2	Semi standard non polar	33892256
4-Amino-7-chloroquinoline,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	1983.8	Standard non polar	33892256
4-Amino-7-chloroquinoline,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2244.0	Standard polar	33892256
4-Amino-7-chloroquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=NC2=CC(Cl)=CC=C12	2149.1	Semi standard non polar	33892256
4-Amino-7-chloroquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=NC2=CC(Cl)=CC=C12	2046.4	Standard non polar	33892256
4-Amino-7-chloroquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=NC2=CC(Cl)=CC=C12	2497.4	Standard polar	33892256
4-Amino-7-chloroquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2377.2	Semi standard non polar	33892256
4-Amino-7-chloroquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2392.5	Standard non polar	33892256
4-Amino-7-chloroquinoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2400.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-7-chloroquinoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0900000000-8e49a2fa9638d485aa96	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-7-chloroquinoline 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-Amino-7-chloroquinoline 10V, Positive-QTOF	splash10-004i-0900000000-e4786754bfb89ef16286	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-7-chloroquinoline 20V, Positive-QTOF	splash10-0fb9-0900000000-2a80184aac2ad23a4f1d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-7-chloroquinoline 40V, Positive-QTOF	splash10-0ik9-0900000000-6963a064d5cc7fc7986b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-7-chloroquinoline 10V, Negative-QTOF	splash10-004i-0900000000-743a71705b0f0c2dcb7f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-7-chloroquinoline 20V, Negative-QTOF	splash10-0fb9-0900000000-47f933a644be92ec1dcb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-7-chloroquinoline 40V, Negative-QTOF	splash10-004i-1900000000-63a8f09f3b6faf75ef27	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

85459

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-Amino-7-chloroquinoline (HMDB0247242)

MOL for HMDB0247242 (4-Amino-7-chloroquinoline)

3D MOL for HMDB0247242 (4-Amino-7-chloroquinoline)

3D SDF for HMDB0247242 (4-Amino-7-chloroquinoline)

3D-SDF for HMDB0247242 (4-Amino-7-chloroquinoline)

PDB for HMDB0247242 (4-Amino-7-chloroquinoline)

3D PDB for HMDB0247242 (4-Amino-7-chloroquinoline)

SMILES for HMDB0247242 (4-Amino-7-chloroquinoline)

INCHI for HMDB0247242 (4-Amino-7-chloroquinoline)

Structure for HMDB0247242 (4-Amino-7-chloroquinoline)

3D Structure for HMDB0247242 (4-Amino-7-chloroquinoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra