3-Methoxy-1,6-diaza-benzo[de]anthracen-7-one

ID: ALA335181

Cas Number: 128129-42-0

PubChem CID: 122683

Max Phase: Preclinical

Molecular Formula: C16H10N2O2

Molecular Weight: 262.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-Methoxysampangine | 3-Methoxysampangine|128129-42-0|CHEMBL335181|SCHEMBL7804334|DTXSID70155819|FBVVMYZYZXYLIA-UHFFFAOYSA-N|7H-Naphtho(1,2,3-ij)(2,7)naphthyridin-7-one, 3-methoxy-|14-methoxy-10,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one

Canonical SMILES:  COc1cnc2c3c(nccc13)C(=O)c1ccccc1-2

Standard InChI:  InChI=1S/C16H10N2O2/c1-20-12-8-18-14-9-4-2-3-5-10(9)16(19)15-13(14)11(12)6-7-17-15/h2-8H,1H3

Standard InChI Key:  FBVVMYZYZXYLIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 23  0  0  0  0  0  0  0  0999 V2000
    6.9990   -9.4816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9990   -8.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -8.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5664   -8.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8504   -8.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1313   -8.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327   -9.4828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -9.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -9.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8540   -9.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2839  -10.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5741  -11.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8593  -10.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474  -11.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1490  -11.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685  -12.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5775  -11.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0057  -11.1267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8521   -7.4054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -6.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  4  2  0
  9 10  1  0
 10 13  1  0
  4  3  1  0
 12 11  1  0
 11  8  1  0
  4  5  1  0
  8  1  2  0
 12 13  1  0
  5  6  2  0
 13 14  2  0
  1  2  1  0
 14 15  1  0
  6  7  1  0
 15 16  2  0
  7 10  2  0
 16 17  1  0
 17 12  2  0
  2  3  2  0
 11 18  2  0
  5 19  1  0
  8  9  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA335181

   3-Methoxysampangine

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 262.27

Molecular Weight (Monoisotopic): 262.0742

AlogP: 2.85

#Rotatable Bonds: 1

Polar Surface Area: 52.08

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.37

CX LogP: 2.27

CX LogD: 2.27

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: 0.78

References

1. Peterson JR, Zjawiony JK, Liu S, Hufford CD, Clark AM, Rogers RD..  (1992)  Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines.,  35  (22): [PMID:1433213] [10.1021/jm00100a012]

2. Muhammad I, Dunbar DC, Takamatsu S, Walker LA, Clark AM..  (2001)  Antimalarial, cytotoxic, and antifungal alkaloids from Duguetia hadrantha.,  64  (5): [PMID:11374943] [10.1021/np000436s]

3. Mishra SK, Tripathi G, Kishore N, Singh RK, Singh A, Tiwari VK..  (2017)  Drug development against tuberculosis: Impact of alkaloids.,  137  [PMID:28628823] [10.1016/j.ejmech.2017.06.005]

Source

Source(1):

• Scientific Literature