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4-(4-hydroxy-3-nitrophenyl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-6-carboxylic acid

ID: ALA3115913

PubChem CID: 4182169

Max Phase: Preclinical

Molecular Formula: C19H16N2O5

Molecular Weight: 352.35

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc2c1NC(c1ccc(O)c([N+](=O)[O-])c1)C1CC=CC21

Standard InChI:  InChI=1S/C19H16N2O5/c22-16-8-7-10(9-15(16)21(25)26)17-12-4-1-3-11(12)13-5-2-6-14(19(23)24)18(13)20-17/h1-3,5-9,11-12,17,20,22H,4H2,(H,23,24)

Standard InChI Key:  GQCJWYDFODGKMZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.8159   -9.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -9.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287  -10.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5269   -8.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414   -9.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2403   -9.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524  -10.3169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6702   -9.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2878   -8.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9559   -7.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1320   -7.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547   -8.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6691   -9.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304  -11.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8177  -11.5567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2448  -11.5538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3825  -10.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799  -11.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0921  -11.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8073  -11.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8058  -10.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0931   -9.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5208  -11.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5200   -9.8975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5183   -9.0735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2345  -10.3080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 12  1  0
  6  7  1  0
  7  8  1  0
  8 13  1  0
 12 13  1  0
 10 11  2  0
  9 10  1  0
 11 12  1  0
 13  9  1  0
  3 14  1  0
 14 15  1  0
 14 16  2  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  8 17  1  0
 20 23  1  0
 24 25  2  0
 24 26  1  0
 21 24  1  0
M  CHG  2  24   1  26  -1
M  END

Associated Targets(Human)

HSPD1 Tbio HSP60/HSP10 (366 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

groL GroEL/GroES (1042 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecium (13803 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae subsp. pneumoniae (55 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterobacter cloacae (7976 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 352.35Molecular Weight (Monoisotopic): 352.1059AlogP: 3.83#Rotatable Bonds: 3
Polar Surface Area: 112.70Molecular Species: ACIDHBA: 5HBD: 3
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 4.56CX Basic pKa: 0.58CX LogP: 3.93CX LogD: 0.43
Aromatic Rings: 2Heavy Atoms: 26QED Weighted: 0.44Np Likeness Score: -0.44

References

1. Johnson SM, Sharif O, Mak PA, Wang HT, Engels IH, Brinker A, Schultz PG, Horwich AL, Chapman E..  (2014)  A biochemical screen for GroEL/GroES inhibitors.,  24  (3): [PMID:24418775] [10.1016/j.bmcl.2013.12.100]
2. Abdeen S, Salim N, Mammadova N, Summers CM, Frankson R, Ambrose AJ, Anderson GG, Schultz PG, Horwich AL, Chapman E, Johnson SM..  (2016)  GroEL/ES inhibitors as potential antibiotics.,  26  (13): [PMID:27184767] [10.1016/j.bmcl.2016.04.089]

Source