MiMeDB: Showing metabocard for 8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid (MMDBc0000994)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 18:40:38 UTC

Update Date

2025-10-07 16:04:24 UTC

Metabolite ID

MMDBc0000994

Metabolite Identification

Common Name

8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid

Description

8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid is a member of the quinoline derivatives chemical class. There is limited literature available on this metabolite, indicating that further research may be needed to fully understand its properties and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004181503492D          

 16 17  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  3 13  2  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000994

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C2C=CC=C(O)C2=NC(=C1)C(S)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO3S/c1-15-9-5-7(11(14)16)12-10-6(9)3-2-4-8(10)13/h2-5,13H,1H3,(H,14,16)

> <INCHI_KEY>
FRALXELBBOKSAT-UHFFFAOYSA-N

> <FORMULA>
C11H9NO3S

> <MOLECULAR_WEIGHT>
235.26

> <EXACT_MASS>
235.030314328

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
23.168851394519976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-hydroxy-4-methoxyquinoline-2-carbothioic S-acid

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
-0.7234073105178109

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.256330636957424

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.5689600359923697

> <JCHEM_PKA_STRONGEST_BASIC>
6.736234160009661

> <JCHEM_POLAR_SURFACE_AREA>
59.42

> <JCHEM_REFRACTIVITY>
61.7214

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-4-methoxyquinoline-2-carbothioic S-acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  S   UNK     0       0.000   1.540   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    3    7                                                  
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

Synonyms

Not Available

Molecular Formula

C₁₁H₉NO₃S

Average Mass

235.26

Monoisotopic Mass

235.030314328

IUPAC Name

8-hydroxy-4-methoxyquinoline-2-carbothioic S-acid

Traditional Name

8-hydroxy-4-methoxyquinoline-2-carbothioic S-acid

CAS Registry Number

Not Available

SMILES

COC1=C2C=CC=C(O)C2=NC(=C1)C(S)=O

InChI Identifier

InChI=1S/C11H9NO3S/c1-15-9-5-7(11(14)16)12-10-6(9)3-2-4-8(10)13/h2-5,13H,1H3,(H,14,16)

InChI Key

FRALXELBBOKSAT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyquinolines. Hydroxyquinolines are compounds containing a quinoline moiety bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Hydroxyquinolines

Direct Parent

Hydroxyquinolines

Alternative Parents

Substituents

Hydroxyquinoline
8-hydroxyquinoline
Pyridine carboxylic acid or derivatives
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyridine
Benzenoid
Heteroaromatic compound
Carbothioic s-acid
Carbodithioic acid
Thiocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Alkylthiol
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.66	ALOGPS
logP	-0.72	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	6.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.42 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.72 m³·mol⁻¹	ChemAxon
Polarizability	23.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	240.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	32.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	362.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	696.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	703.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	438.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2479.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	210.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	539.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	419.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	313.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	293.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	172.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	203.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	489.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	368.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	654.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1466.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1152.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid_TMS_1	COC1=CC(C(=O)S)=NC2=C(O[Si](C)(C)C)C=CC=C12	standard non polar	2025-10-23	1885.55
Gas Chromatography	8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid_TMS_2	COC1=CC(C(=O)S[Si](C)(C)C)=NC2=C(O)C=CC=C12	standard non polar	2025-10-23	1908.39
Gas Chromatography	8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid_TMS_3	COC1=CC(C(=O)S[Si](C)(C)C)=NC2=C(O[Si](C)(C)C)C=CC=C12	standard non polar	2025-10-23	1952.22
Gas Chromatography	8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid_TMS_1	COC1=CC(C(=O)S)=NC2=C(O[Si](C)(C)C)C=CC=C12	standard polar	2025-10-23	2482.95
Gas Chromatography	8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid_TMS_2	COC1=CC(C(=O)S[Si](C)(C)C)=NC2=C(O)C=CC=C12	standard polar	2025-10-23	2554.04
Gas Chromatography	8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid_TMS_3	COC1=CC(C(=O)S[Si](C)(C)C)=NC2=C(O[Si](C)(C)C)C=CC=C12	standard polar	2025-10-23	2397.1

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human subgingival plaque	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86002113

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 8-Hydroxy-4-methoxyquinoline-2-carbothioic S-acid (MMDBc0000994)

MOL for #<Metabolite:0x00007f9af076f6f0>

3D MOL for #<Metabolite:0x00007f9af076f6f0>

3D SDF for #<Metabolite:0x00007f9af076f6f0>

3D-SDF for #<Metabolite:0x00007f9af076f6f0>

PDB for #<Metabolite:0x00007f9af076f6f0>

3D PDB for #<Metabolite:0x00007f9af076f6f0>

SMILES for #<Metabolite:0x00007f9af076f6f0>

INCHI for #<Metabolite:0x00007f9af076f6f0>

Structure for #<Metabolite:0x00007f9af076f6f0>

3D Structure for #<Metabolite:0x00007f9af076f6f0>