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

ID: ALA5206861

PubChem CID: 168295185

Max Phase: Preclinical

Molecular Formula: C14H13NO5

Molecular Weight: 275.26

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H13NO5/c1-2-5-20-15-7-8-6-11(18)12-9(16)3-4-10(17)13(12)14(8)19/h3-4,6-7,18-19H,2,5H2,1H3/b15-7+

Standard InChI Key:  QMAPBXPWCZAOII-VIZOYTHASA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -2.5004    1.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859    2.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714    1.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714    0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859    0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004    0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    2.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538    0.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859    2.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -0.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538   -0.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    2.8838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719   -0.4112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -1.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004   -2.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004   -2.8855    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
 18 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5206861

   ---

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: 275.26

Molecular Weight (Monoisotopic): 275.0794

AlogP: 1.79

#Rotatable Bonds: 4

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: 2.10

CX LogP: 3.17

CX LogD: 3.06

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.38

Np Likeness Score: 0.78

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