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

ID: ALA267024

Chembl Id: CHEMBL267024

Max Phase: Preclinical

Molecular Formula: C21H22O6

Molecular Weight: 370.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dimethylacrylshikonin

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

Standard InChI:  InChI=1S/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3/t17-/m1/s1

Standard InChI Key:  BATBOVZTQBLKIL-QGZVFWFLSA-N

Alternative Forms

1. Parent:

   

   ALA267024

   DIMETHYLACRYLSHIKONIN

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: 370.40

Molecular Weight (Monoisotopic): 370.1416

AlogP: 3.64

#Rotatable Bonds: 5

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: 5.07

CX LogD: 5.04

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.36

Np Likeness Score: 2.11

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. 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]

3. 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]

4. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

5. 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]

6. 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]

7. 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]

8. 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