ID: ALA3327388

Max Phase: Preclinical

Molecular Formula: C23H30N2O6

Molecular Weight: 430.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc([C@H](CC=C(C)C)OC(=O)CC(C)C)c(OC)c2c1/C(=N/O)C=C/C2=N\O

Standard InChI:  InChI=1S/C23H30N2O6/c1-13(2)7-10-18(31-20(26)11-14(3)4)15-12-19(29-5)21-16(24-27)8-9-17(25-28)22(21)23(15)30-6/h7-9,12,14,18,27-28H,10-11H2,1-6H3/b24-16+,25-17+/t18-/m0/s1

Standard InChI Key:  KSNHMNQDRBNSEV-IMSPSDRLSA-N

Molecule Features

Natural Product: No

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

Properties

Molecular Weight: 430.50

Molecular Weight (Monoisotopic): 430.2104

AlogP: 4.62

#Rotatable Bonds: 8

Polar Surface Area: 109.94

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 5.02

CX Basic pKa:

CX LogP: 4.01

CX LogD: 1.77

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: 1.01

References

1. Wang R, Zhang X, Song H, Zhou S, Li S..  (2014)  Synthesis and evaluation of novel alkannin and shikonin oxime derivatives as potent antitumor agents.,  24  (17): [PMID:25127868] [10.1016/j.bmcl.2014.07.012]

2. Stallinger A, Kretschmer N, Kleinegger F, Brvar L, Liegl-Atzwanger B, Prokesch A, Durchschein C, Bauer R, Deutsch A, Rinner B..  (2020)  β,β-Dimethylacrylshikonin Induces Apoptosis in Melanoma Cell Lines by NOXA Upregulation.,  83  (2): [PMID:31961147] [10.1021/acs.jnatprod.9b00719]

3. 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