MiMeDB: Showing metabocard for Quinolobactin (MMDBc0017909)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 08:11:35 UTC

Update Date

2025-10-07 16:06:45 UTC

Metabolite ID

MMDBc0017909

Metabolite Identification

Common Name

Quinolobactin

Description

Quinolobactin is a siderophore belonging to the chemical class of quinoline derivatives. Its chemical structure is characterized by a quinoline core, which is modified to facilitate iron chelation, a critical function in microbial iron acquisition. Quinolobactin is synthesized through biosynthetic pathways that involve various gene clusters, as evidenced by metagenomic analyses revealing its presence alongside other metabolites like bacillibactin and ectoine (PMID:34827320 ). In Pseudomonas fluorescens, quinolobactin is produced under iron-limiting conditions, alongside pyoverdine, highlighting its role in microbial survival and competition (PMID:17222140 ). This compound has been shown to exhibit antimicrobial properties, particularly against phytopathogenic organisms such as Pythium debaryanum (PMID:24756978 ). Furthermore, quinolobactin exists in various forms, including thioquinolobactin, which is a derivative that results from the hydrolysis of 8-hydroxy-4-methoxy-2-quinoline thiocarboxylic acid (PMID:17222140 ). The diversity of structures among secondary siderophores, including quinolobactin, underscores the complexity of microbial strategies for iron acquisition (PMID:32011068 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251502542D          

 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 O   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>
MMDBc0017909

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO4/c1-16-9-5-7(11(14)15)12-10-6(9)3-2-4-8(10)13/h2-5,13H,1H3,(H,14,15)

> <INCHI_KEY>
BBZLFYDYFRWHEF-UHFFFAOYSA-N

> <FORMULA>
C11H9NO4

> <MOLECULAR_WEIGHT>
219.196

> <EXACT_MASS>
219.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.078033887430323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-4-methoxyquinoline-2-carboxylic acid

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
-0.29735283967948367

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.273935397766207

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1359813680654858

> <JCHEM_PKA_STRONGEST_BASIC>
6.827573748027946

> <JCHEM_POLAR_SURFACE_AREA>
79.65

> <JCHEM_REFRACTIVITY>
55.3076

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-4-methoxyquinoline-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-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  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+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

Value	Source
8-Hydroxy-4-methoxyquinoline-2-carboxylate	Generator
8-Hydroxy-4-methoxy-quinaldic acid	MeSH
Quinolobactin	MeSH

Molecular Formula

C₁₁H₉NO₄

Average Mass

219.196

Monoisotopic Mass

219.053157774

IUPAC Name

8-hydroxy-4-methoxyquinoline-2-carboxylic acid

Traditional Name

8-hydroxy-4-methoxyquinoline-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H9NO4/c1-16-9-5-7(11(14)15)12-10-6(9)3-2-4-8(10)13/h2-5,13H,1H3,(H,14,15)

InChI Key

BBZLFYDYFRWHEF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-2-carboxylic acid
Hydroxyquinoline
8-hydroxyquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyridine
Benzenoid
Heteroaromatic compound
Ether
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
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	1.11 g/L	ALOGPS
logP	2.18	ALOGPS
logP	-0.3	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.14	ChemAxon
pKa (Strongest Basic)	6.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.31 m³·mol⁻¹	ChemAxon
Polarizability	21.08 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	247.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	57.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	301.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	327.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	443.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	307.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1595.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	401.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	520.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	245.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	326.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	183.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	105.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	178.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	536.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	89.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	378.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1167.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	713.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Quinolobactin_TMS_1	COC1=CC(C(=O)O)=NC2=C(O[Si](C)(C)C)C=CC=C12	standard non polar	2025-10-23	2047.4
Gas Chromatography	Quinolobactin_TMS_2	COC1=CC(C(=O)O[Si](C)(C)C)=NC2=C(O)C=CC=C12	standard non polar	2025-10-23	1884.6
Gas Chromatography	Quinolobactin_TMS_3	COC1=CC(C(=O)O[Si](C)(C)C)=NC2=C(O[Si](C)(C)C)C=CC=C12	standard non polar	2025-10-23	1681.21
Gas Chromatography	Quinolobactin_TMS_1	COC1=CC(C(=O)O)=NC2=C(O[Si](C)(C)C)C=CC=C12	standard polar	2025-10-23	2065.56
Gas Chromatography	Quinolobactin_TMS_2	COC1=CC(C(=O)O[Si](C)(C)C)=NC2=C(O)C=CC=C12	standard polar	2025-10-23	1496.21
Gas Chromatography	Quinolobactin_TMS_3	COC1=CC(C(=O)O[Si](C)(C)C)=NC2=C(O[Si](C)(C)C)C=CC=C12	standard polar	2025-10-23	1328.49

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	2	Human feces; Human sputum; Human urine; Human supragingival plaque; Human ; Human saliva; Human mucosa; 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

Not Available

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 Quinolobactin (MMDBc0017909)

MOL for #<Metabolite:0x00007fc93e4ede50>

3D MOL for #<Metabolite:0x00007fc93e4ede50>

3D SDF for #<Metabolite:0x00007fc93e4ede50>

3D-SDF for #<Metabolite:0x00007fc93e4ede50>

PDB for #<Metabolite:0x00007fc93e4ede50>

3D PDB for #<Metabolite:0x00007fc93e4ede50>

SMILES for #<Metabolite:0x00007fc93e4ede50>

INCHI for #<Metabolite:0x00007fc93e4ede50>

Structure for #<Metabolite:0x00007fc93e4ede50>

3D Structure for #<Metabolite:0x00007fc93e4ede50>