ID: ALA28457

Max Phase: Preclinical

Molecular Formula: C16H16O5

Molecular Weight: 288.30

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(C)=CC[C@H](O)C1=CC(=O)c2c(O)ccc(O)c2C1=O

Standard InChI:  InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1

Standard InChI Key:  NEZONWMXZKDMKF-JTQLQIEISA-N

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

Properties

Molecular Weight: 288.30

Molecular Weight (Monoisotopic): 288.0998

AlogP: 2.12

#Rotatable Bonds: 3

Polar Surface Area: 94.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.50

CX Basic pKa:

CX LogP: 3.01

CX LogD: 2.98

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.58

Np Likeness Score: 2.15

References

1. Lu Q, Liu W, Ding J, Cai J, Duan W..  (2002)  Shikonin derivatives: synthesis and inhibition of human telomerase.,  12  (10): [PMID:11992780] [10.1016/s0960-894x(02)00158-0]

2. Plyta ZF, Li T, Papageorgiou VP, Mellidis AS, Assimopoulou AN, Pitsinos EN, Couladouros EA..  (1998)  Inhibition of topoisomerase I by naphthoquinone derivatives.,  8  (23): [PMID:9873739] [10.1016/s0960-894x(98)00600-3]

3. Tanaka S, Tajima M, Tsukada M, Tabata M..  (1986)  A comparative study on anti-inflammatory activities of the enantiomers, shikonin and alkannin.,  49  (3): [PMID:3760886] [10.1021/np50045a014]

4. Shen CC, Syu WJ, Li SY, Lin CH, Lee GH, Sun CM..  (2002)  Antimicrobial activities of naphthazarins from Arnebia euchroma.,  65  (12): [PMID:12502328] [10.1021/np010599w]

5. Sevimli-Gur C, Akgun IH, Deliloglu-Gurhan I, Korkmaz KS, Bedir E..  (2010)  Cytotoxic naphthoquinones from Alkanna cappadocica ( perpendicular).,  73  (5): [PMID:20405844] [10.1021/np900778j]

6. He H, Bai LP, Jiang ZH..  (2012)  Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin.,  22  (4): [PMID:22281188] [10.1016/j.bmcl.2011.12.143]

7. 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]

8. Arora S, Joshi G, Chaturvedi A, Heuser M, Patil S, Kumar R..  (2022)  A Perspective on Medicinal Chemistry Approaches for Targeting Pyruvate Kinase M2.,  65  (2.0): [PMID:34726055] [10.1021/acs.jmedchem.1c00981]

9. 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