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

ID: ALA9416

Chembl Id: CHEMBL9416

Max Phase: Preclinical

Molecular Formula: C20H22O6

Molecular Weight: 358.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isobutylshikonin

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

Standard InChI:  InChI=1S/C20H22O6/c1-10(2)5-8-16(26-20(25)11(3)4)12-9-15(23)17-13(21)6-7-14(22)18(17)19(12)24/h5-7,9,11,16,21-22H,8H2,1-4H3/t16-/m1/s1

Standard InChI Key:  BVRYLTBIGIAADD-MRXNPFEDSA-N

Alternative Forms

1. Parent:

   

   ALA9416

   ISOBUTYLSHIKONIN

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: 358.39

Molecular Weight (Monoisotopic): 358.1416

AlogP: 3.33

#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: 4.70

CX LogD: 4.66

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.48

Np Likeness Score: 2.09

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. 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]

3. 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]

4. 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]

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. 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