1,4-dihydroxy-5,8-dioxo-5,8-dihydronaphthalene-2-carbaldehyde O-methyl oxime

ID: ALA5209498

PubChem CID: 168296389

Max Phase: Preclinical

Molecular Formula: C12H9NO5

Molecular Weight: 247.21

Names and Identifiers

Canonical SMILES:  CO/N=C/c1cc(O)c2c(c1O)C(=O)C=CC2=O

Standard InChI:  InChI=1S/C12H9NO5/c1-18-13-5-6-4-9(16)10-7(14)2-3-8(15)11(10)12(6)17/h2-5,16-17H,1H3/b13-5+

Standard InChI Key:  NSFPCJMIOQZNRR-WLRTZDKTSA-N

Molfile:  

 
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.1431    1.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    1.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    1.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0017    1.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128    1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032   -0.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    2.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.0325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032   -1.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0017    2.2650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -1.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -2.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  2  0
  6  5  1  0
  3  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  2 11  2  0
  5 12  2  0
 10 13  1  0
  7 14  1  0
  9 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5209498

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 247.21

Molecular Weight (Monoisotopic): 247.0481

AlogP: 1.01

#Rotatable Bonds: 2

Polar Surface Area: 96.19

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.96

CX Basic pKa: 1.92

CX LogP: 2.29

CX LogD: 2.18

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.46

Np Likeness Score: 0.91

References

1. Valipour M..  (2022)  Recent advances of antitumor shikonin/alkannin derivatives: A comprehensive overview focusing on structural classification, synthetic approaches, and mechanisms of action.,  235  [PMID:35367708] [10.1016/j.ejmech.2022.114314]

Source

Source(1):

• Scientific Literature