(S)-6-(3-aminopyrrolidin-1-yl)-5-fluoro-3-oxo-3H-benzofuro[2,3-b]pyrido[3,2,1-kl]phenoxazine-2-carboxylic acid

ID: ALA2008925

PubChem CID: 6712757

Max Phase: Preclinical

Molecular Formula: C26H18FN3O5

Molecular Weight: 471.44

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  N[C@H]1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn4c3c2Oc2cc3c(cc2-4)oc2ccccc23)C1

Standard InChI:  InChI=1S/C26H18FN3O5/c27-17-7-15-22-25(23(17)29-6-5-12(28)10-29)35-21-8-14-13-3-1-2-4-19(13)34-20(14)9-18(21)30(22)11-16(24(15)31)26(32)33/h1-4,7-9,11-12H,5-6,10,28H2,(H,32,33)/t12-/m0/s1

Standard InChI Key:  MVQGDECFIIBKAY-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 35 41  0  0  1  0  0  0  0  0999 V2000
    2.0036   -1.1749    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8316   -0.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5142    1.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    1.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2374    3.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8234    3.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940    0.8696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5365   -1.7854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035   -3.5729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464    0.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652   -0.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3604    0.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1799    0.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -0.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176   -0.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0080    1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5323    0.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2457   -0.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7064   -0.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0902    0.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898    2.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2668   -2.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -2.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1471   -0.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9145    0.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1275   -2.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111   -3.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9714   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3551   -0.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0
  2 11  1  0
  2 14  1  0
  3 18  1  0
  3 26  1  0
  4 16  2  0
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  7 10  1  0
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 30 34  2  0
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 34 35  1  0
M  END

Associated Targets(Human)

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP2A Tclin DNA topoisomerase II (1334 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

Calculated Properties

Molecular Weight: 471.44Molecular Weight (Monoisotopic): 471.1230AlogP: 4.37#Rotatable Bonds: 2
Polar Surface Area: 110.93Molecular Species: ZWITTERIONHBA: 7HBD: 2
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 5.27CX Basic pKa: 9.63CX LogP: 0.92CX LogD: 0.92
Aromatic Rings: 5Heavy Atoms: 35QED Weighted: 0.39Np Likeness Score: -0.20

References

1. Xu H, Hurley LH..  (2022)  A first-in-class clinical G-quadruplex-targeting drug. The bench-to-bedside translation of the fluoroquinolone QQ58 to CX-5461 (Pidnarulex).,  77  [PMID:36195286] [10.1016/j.bmcl.2022.129016]
2. Yu, Xufen and 6 more authors.  2017-01-05  Synthesis, evaluation, and CoMFA study of fluoroquinophenoxazine derivatives as bacterial topoisomerase IA inhibitors.  [PMID:27689733]
3. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]
4. Abraham, Adedoyin D and 18 more authors.  2019-11-27  Drug Design Targeting T-Cell Factor-Driven Epithelial-Mesenchymal Transition as a Therapeutic Strategy for Colorectal Cancer.  [PMID:31675229]

Source