NP-MRD: Showing NP-Card for Quinolobactin (NP0003130)

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Record Information

Version

2.0

Created at

2020-12-09 00:12:48 UTC

Updated at

2021-07-15 16:45:35 UTC

NP-MRD ID

NP0003130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinolobactin

Provided By

NPAtlas

Description

Quinolobactin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Quinolobactin is found in Pseudomonas and Pseudomonas fluorescens. Quinolobactin was first documented in 2000 (PMID: 10653708). Based on a literature review a small amount of articles have been published on quinolobactin (PMID: 14663086) (PMID: 15066027) (PMID: 15689111) (PMID: 32011068).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117453D          

 25 26  0  0  0  0            999 V2000
   -2.2073   -2.6276    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0321   -1.2460    0.3749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167   -0.6437    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921   -1.4455   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405   -0.8838   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7047   -1.7219   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8087   -1.2078   -0.7622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5830   -3.0847   -0.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    0.4629   -0.4458 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345    1.2739   -0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854    2.6478   -0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9203    3.2142   -0.6985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3995    3.4595   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427    2.8923    0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267    1.5320    0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7217    0.7242   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796   -3.0307    1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460   -2.8693    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033   -3.1039   -0.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -2.5277    0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3299   -3.7095   -0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651    2.6983   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930    4.5477   -0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    3.5308    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8112    1.1184    0.3642 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16  3  1  0  0  0  0
 16 10  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  0  0  0  0
 12 22  1  0  0  0  0
 13 23  1  0  0  0  0
 14 24  1  0  0  0  0
 15 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003130

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=NC2=C(O[H])C([H])=C([H])C([H])=C2C(OC([H])([H])[H])=C1[H]

> <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>
21.343613520748253

> <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>
55.307600000000015

> <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                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.207  -2.628   0.504  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.032  -1.246   0.375  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.817  -0.644   0.098  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.292  -1.446  -0.063  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.541  -0.884  -0.344  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.705  -1.722  -0.513  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.809  -1.208  -0.762  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.583  -3.085  -0.396  0.00  0.00           O+0
HETATM    9  N   UNK     0       1.590   0.463  -0.446  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.535   1.274  -0.296  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.685   2.648  -0.420  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.920   3.214  -0.699  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.400   3.459  -0.265  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.643   2.892   0.016  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.827   1.532   0.145  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.722   0.724  -0.015  0.00  0.00           C+0
HETATM   17  H   UNK     0      -1.380  -3.031   1.152  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.146  -2.869   1.058  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.203  -3.104  -0.504  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.240  -2.528   0.021  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.330  -3.709  -0.127  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.765   2.698  -0.827  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.293   4.548  -0.360  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.514   3.531   0.141  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.811   1.118   0.364  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   21                                                       
CONECT    9    5   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   22                                                       
CONECT   13   11   14   23                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15    3   10                                                  
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    8                                                            
CONECT   22   12                                                            
CONECT   23   13                                                            
CONECT   24   14                                                            
CONECT   25   15                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-Methoxy-8-hydroxyquinoline-2-carboxylic acid	ChEBI
8-Hydroxy-4-methoxy-quinaldic acid	ChEBI
8-Hydroxy-4-methoxyquinaldic acid	ChEBI
4-Methoxy-8-hydroxyquinoline-2-carboxylate	Generator
8-Hydroxy-4-methoxy-quinaldate	Generator
8-Hydroxy-4-methoxyquinaldate	Generator
Quinolobactin	MeSH
8-Hydroxy-4-methoxyquinoline-2-carboxylate	Generator

Chemical Formula

C₁₁H₉NO₄

Average Mass

219.1960 Da

Monoisotopic Mass

219.05316 Da

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=CC(=NC2=C1C=CC=C2O)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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudomonas	NPAtlas	10653708
Pseudomonas fluorescens	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Pseudomonas fluorescens ATCC17400	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound 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

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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	21.34 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

External Links

NPAtlas ID

NPA017785

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026479

Chemspider ID

21431229

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

171659

Good Scents ID

Not Available

References

General References

Mossialos D, Meyer JM, Budzikiewicz H, Wolff U, Koedam N, Baysse C, Anjaiah V, Cornelis P: Quinolobactin, a new siderophore of Pseudomonas fluorescens ATCC 17400, the production of which is repressed by the cognate pyoverdine. Appl Environ Microbiol. 2000 Feb;66(2):487-92. doi: 10.1128/aem.66.2.487-492.2000. [PubMed:10653708 ]
Baysse C, Matthijs S, Schobert M, Layer G, Jahn D, Cornelis P: Co-ordination of iron acquisition, iron porphyrin chelation and iron-protoporphyrin export via the cytochrome c biogenesis protein CcmC in Pseudomonas fluorescens. Microbiology (Reading). 2003 Dec;149(Pt 12):3543-3552. doi: 10.1099/mic.0.26566-0. [PubMed:14663086 ]
Matthijs S, Baysse C, Koedam N, Tehrani KA, Verheyden L, Budzikiewicz H, Schafer M, Hoorelbeke B, Meyer JM, De Greve H, Cornelis P: The Pseudomonas siderophore quinolobactin is synthesized from xanthurenic acid, an intermediate of the kynurenine pathway. Mol Microbiol. 2004 Apr;52(2):371-84. doi: 10.1111/j.1365-2958.2004.03999.x. [PubMed:15066027 ]
du Dhardemare AM, Serratrice G, Pierre JL: Synthesis and iron-binding properties of quinolobactin, a siderophore from a pyoverdine-deficient Pseudomonas fluorescens. Biometals. 2004 Dec;17(6):691-7. doi: 10.1007/s10534-004-1205-0. [PubMed:15689111 ]
Schalk IJ, Rigouin C, Godet J: An overview of siderophore biosynthesis among fluorescent Pseudomonads and new insights into their complex cellular organization. Environ Microbiol. 2020 Apr;22(4):1447-1466. doi: 10.1111/1462-2920.14937. Epub 2020 Feb 19. [PubMed:32011068 ]

Showing NP-Card for Quinolobactin (NP0003130)

MOL for NP0003130 (Quinolobactin)

3D MOL for NP0003130 (Quinolobactin)

3D SDF for NP0003130 (Quinolobactin)

3D-SDF for NP0003130 (Quinolobactin)

PDB for NP0003130 (Quinolobactin)

3D PDB for NP0003130 (Quinolobactin)

SMILES for NP0003130 (Quinolobactin)

INCHI for NP0003130 (Quinolobactin)

Structure for NP0003130 (Quinolobactin)

3D Structure for NP0003130 (Quinolobactin)