10-methoxycanthin-6-one

ID: ALA454057

Cas Number: 86293-40-5

PubChem CID: 158928

Max Phase: Preclinical

Molecular Formula: C15H10N2O2

Molecular Weight: 250.26

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Synonyms: NSC-341584 | 6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-one, 10-methoxy-|86293-40-5|NSC-341584|6H-Indolo[3,2,1-de][1,5]naphthyridin-6-one, 10-methoxy-|NSC341584|10-methoxycanthin-6-one|CHEMBL454057|SCHEMBL12762822|DTXSID80235474|NSC 341584|CANTHIN-6-ONE, 10-METHOXY- K237|InChI=1/C15H10N2O2/c1-19-9-2-4-13-11(8-9)10-6-7-16-12-3-5-14(18)17(13)15(10)12/h2-8H,1H

Canonical SMILES:  COc1ccc2c(c1)c1ccnc3ccc(=O)n2c31

Standard InChI:  InChI=1S/C15H10N2O2/c1-19-9-2-4-13-11(8-9)10-6-7-16-12-3-5-14(18)17(13)15(10)12/h2-8H,1H3

Standard InChI Key:  FDBMONUDUKGKGY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 22  0  0  0  0  0  0  0  0999 V2000
   -3.9789    1.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9789    0.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2655    0.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    1.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    1.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5515    0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7640    1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395    1.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5543    2.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3924    2.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3194    0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786    0.2974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3651   -0.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5466    0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8170   -1.1273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6935    1.7998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4023    1.3938    0.0000 C   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
  6 12  1  0
  7  5  1  0
  7 11  1  0
 16  8  1  0
  8  9  2  0
  9 10  1  0
 10  7  2  0
 11 12  1  0
 11 16  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 13 17  2  0
  1 18  1  0
 18 19  1  0
M  END

Associated Targets(Human)

KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCC1395 (122 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Calf thymus DNA (4845 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cryptococcus neoformans (21258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichophyton mentagrophytes (4846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus fumigatus (16427 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus cereus (7522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ralstonia solanacearum (520 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 250.26Molecular Weight (Monoisotopic): 250.0742AlogP: 2.45#Rotatable Bonds: 1
Polar Surface Area: 43.60Molecular Species: NEUTRALHBA: 4HBD:
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 4.01CX LogP: 1.66CX LogD: 1.66
Aromatic Rings: 4Heavy Atoms: 19QED Weighted: 0.52Np Likeness Score: 0.11

References

1. Arisawa M, Kinghorn AD, Cordell GA, Farnsworth NR..  (1983)  Plant anticancer agents. XXIV. Alkaloid constituents of Simaba multiflora.,  46  (2): [PMID:6875577] [10.1021/np50026a016]
2. Soriano-Agatón F, Lagoutte D, Poupon E, Roblot F, Fournet A, Gantier JC, Hocquemiller R..  (2005)  Extraction, hemisynthesis, and synthesis of canthin-6-one analogues. Evaluation of their antifungal activities.,  68  (11): [PMID:16309303] [10.1021/np050250z]
3. Pezzuto JM, Che CT, McPherson DD, Zhu JP, Topcu G, Erdelmeier CA, Cordell GA..  (1991)  DNA as an affinity probe useful in the detection and isolation of biologically active natural products.,  54  (6): [PMID:1812211] [10.1021/np50078a006]
4. Cebrian-Torrejon G, Kahn SA, Ferreira ME, Thirant C, Rojas de Arias A, Figadere B, Fournet A, Chneiweiss H, Poupon E.  (2012)  Alkaloids from Rutaceae: activities of canthin-6-one alkaloids and synthetic analogues on glioblastoma stems cells,  (7): [10.1039/C2MD20047C]
5. Dai J, Dan W, Zhang Y, He M, Wang J..  (2018)  Design and synthesis of C10 modified and ring-truncated canthin-6-one analogues as effective membrane-active antibacterial agents.,  28  (18): [PMID:30097370] [10.1016/j.bmcl.2018.06.001]
6. Luo B, Song X..  (2021)  A comprehensive overview of β-carbolines and its derivatives as anticancer agents.,  224  [PMID:34332400] [10.1016/j.ejmech.2021.113688]

Source