1,6-Diaza-benzo[de]anthracen-7-one

ID: ALA435201

Cas Number: 116664-93-8

PubChem CID: 387195

Max Phase: Preclinical

Molecular Formula: C15H8N2O

Molecular Weight: 232.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Sampangine | Sampangine|116664-93-8|F1EAG7D138|CHEBI:67606|NSC680736|1,6-Diaza-benzo(de)anthracen-7-one|1,6-Diaza-benzo[de]anthracen-7-one|UNII-F1EAG7D138|7H-naphtho[1,2,3-ij][2,7]naphthyridin-7-one|NSC 680736|NSC-680736|7H-NAPHTHO(1,2,3-IJ)(2,7)NAPHTHYRIDIN-7-ONE|sampan-gine|SAMPANGIN|CHEMBL435201|SCHEMBL6230423|DTXSID3041118|BWQKHOMAOVUASZ-UHFFFAOYSA-N|BDBM50478733|BC-1-21|Q6118076|7H-Naphtho[1,2,3,-ij][2,7]naphthyridin-7-one, 9CI|10,16-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-1(17),2Show More⌵

Canonical SMILES:  O=C1c2ccccc2-c2nccc3ccnc1c23

Standard InChI:  InChI=1S/C15H8N2O/c18-15-11-4-2-1-3-10(11)13-12-9(5-7-16-13)6-8-17-14(12)15/h1-8H

Standard InChI Key:  BWQKHOMAOVUASZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 21  0  0  0  0  0  0  0  0999 V2000
   -4.4489    1.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4501    0.8494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7397    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220    1.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5907    0.8578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958    1.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3117    2.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3055    0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0237    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7332    0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7308   -0.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968   -0.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -0.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0115   -1.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967   -2.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5810   -1.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5850   -0.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419   -0.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  1  2  2  0
  4  9  1  0
  2 10  1  0
  8 12  1  0
  9 10  2  0
 10 11  1  0
 11 13  1  0
  8  5  2  0
 12 13  2  0
  5  6  1  0
 13 14  1  0
  4  3  2  0
 14 15  2  0
  6  7  2  0
 15 16  1  0
  7  4  1  0
 16 17  2  0
 17 12  1  0
  8  9  1  0
 11 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA435201

   SAMPANGINE

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: 232.24

Molecular Weight (Monoisotopic): 232.0637

AlogP: 2.84

#Rotatable Bonds: ┄

Polar Surface Area: 42.85

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.91

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.47

Np Likeness Score: 0.64

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. Orabi KY, Li E, Clark AM, Hufford CD..  (1999)  Microbial transformation of sampangine.,  62  (7): [PMID:10425122] [10.1021/np980457a]

3. Orabi KY, Walker LA, Clark AM, Hufford CD..  (2000)  Characterization of the major metabolite of sampangine in rats.,  63  (5): [PMID:10843589] [10.1021/np990552z]

4. 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]

5. Pan E, Cao S, Brodie PJ, Callmander MW, Randrianaivo R, Rakotonandrasana S, Rakotobe E, Rasamison VE, TenDyke K, Shen Y, Suh EM, Kingston DG..  (2011)  Isolation and synthesis of antiproliferative eupolauridine alkaloids of Ambavia gerrardii from the Madagascar Dry Forest.,  74  (5): [PMID:21504145] [10.1021/np200093n]

6. Claes P, Cappoen D, Mbala BM, Jacobs J, Mertens B, Mathys V, Verschaeve L, Huygen K, De Kimpe N..  (2013)  Synthesis and antimycobacterial activity of analogues of the bioactive natural products sampangine and cleistopholine.,  67  [PMID:23850570] [10.1016/j.ejmech.2013.06.010]

7. Jiang Z, Liu N, Dong G, Jiang Y, Liu Y, He X, Huang Y, He S, Chen W, Li Z, Yao J, Miao Z, Zhang W, Sheng C..  (2014)  Scaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans.,  24  (17): [PMID:25115626] [10.1016/j.bmcl.2014.07.064]

8. Mahdi F, Morgan JB, Liu W, Agarwal AK, Jekabsons MB, Liu Y, Zhou YD, Nagle DG..  (2015)  Sampangine (a Copyrine Alkaloid) Exerts Biological Activities through Cellular Redox Cycling of Its Quinone and Semiquinone Intermediates.,  78  (12): [PMID:26637046] [10.1021/acs.jnatprod.5b00819]

9. Liu N, Zhong H, Tu J, Jiang Z, Jiang Y, Jiang Y, Jiang Y, Li J, Zhang W, Wang Y, Sheng C..  (2018)  Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors.,  143  [PMID:29126739] [10.1016/j.ejmech.2017.10.043]

10. 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