Acetic acid (R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-4-methyl-pent-3-enyl ester

ID: ALA403516

Chembl Id: CHEMBL403516

Max Phase: Preclinical

Molecular Formula: C18H18O6

Molecular Weight: 330.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3/t15-/m1/s1

Standard InChI Key:  WNFXUXZJJKTDOZ-OAHLLOKOSA-N

Alternative Forms

1. Parent:

   

   ALA403516

   ACETYLSHIKONIN

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: 330.34

Molecular Weight (Monoisotopic): 330.1103

AlogP: 2.69

#Rotatable Bonds: 4

Polar Surface Area: 100.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 3.45

CX LogD: 3.42

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: 2.31

References

1. Ahn BZ, Baik KU, Kweon GR, Lim K, Hwang BD..  (1995)  Acylshikonin analogues: synthesis and inhibition of DNA topoisomerase-I.,  38  (6): [PMID:7699697] [10.1021/jm00006a025]

2. 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]

3. Wei BL, Teng CH, Wang JP, Won SJ, Lin CN..  (2007)  Synthetic 2',5'-dimethoxychalcones as G(2)/M arrest-mediated apoptosis-inducing agents and inhibitors of nitric oxide production in rat macrophages.,  42  (5): [PMID:17320246] [10.1016/j.ejmech.2006.12.009]

4. An S, Park YD, Paik YK, Jeong TS, Lee WS..  (2007)  Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon.,  17  (4): [PMID:17157006] [10.1016/j.bmcl.2006.11.024]

5. Cui XR, Tsukada M, Suzuki N, Shimamura T, Gao L, Koyanagi J, Komada F, Saito S..  (2008)  Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones.,  43  (6): [PMID:17949858] [10.1016/j.ejmech.2007.08.009]

6. 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]

7. Kim JY, Jeong HJ, Park JY, Kim YM, Park SJ, Cho JK, Park KH, Ryu YB, Lee WS..  (2012)  Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.,  20  (5): [PMID:22300884] [10.1016/j.bmc.2012.01.011]

8. Kretschmer N, Rinner B, Deutsch AJ, Lohberger B, Knausz H, Kunert O, Blunder M, Boechzelt H, Schaider H, Bauer R..  (2012)  Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.,  75  (5): [PMID:22530779] [10.1021/np2006499]

9. LI C, FUKUSHI Y, KAWABATA J, TAHARA S, MIZUTANI J, UYEDA I.  (1998)  Antiviral and Antifungal Activities of Some Naphthoquinones Isolated from the Roots of Lithospermum erythrorhizon,  23  (1): [10.1584/jpestics.23.54]

10. Wasilewicz A, Kirchweger B, Bojkova D, Abi Saad MJ, Langeder J, Bütikofer M, Adelsberger S, Grienke U, Cinatl J, Petermann O, Scapozza L, Orts J, Kirchmair J, Rabenau HF, Rollinger JM..  (2023)  Identification of Natural Products Inhibiting SARS-CoV-2 by Targeting Viral Proteases: A Combined in Silico and in Vitro Approach.,  86  (2.0): [PMID:36651644] [10.1021/acs.jnatprod.2c00843]

Source

Source(1):

• Scientific Literature