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ID: ALA8951
Max Phase: Preclinical
Molecular Formula: C19H20O6
Molecular Weight: 344.36
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCC(=O)O[C@H](CC=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O
Standard InChI: InChI=1S/C19H20O6/c1-4-16(23)25-15(8-5-10(2)3)11-9-14(22)17-12(20)6-7-13(21)18(17)19(11)24/h5-7,9,15,20-21H,4,8H2,1-3H3/t15-/m1/s1
Standard InChI Key: DLBQFLWCDFTEQG-OAHLLOKOSA-N
Associated Targets(Human)
DNA topoisomerase I 7553 Activities
Acyl coenzyme A:cholesterol acyltransferase 1 857 Activities
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Acyl coenzyme A:cholesterol acyltransferase 2 288 Activities
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Associated Targets(non-human)
Cladosporium herbarum 157 Activities
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Tobacco mosaic virus 2972 Activities
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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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 344.36 | Molecular Weight (Monoisotopic): 344.1260 | AlogP: 3.08 | #Rotatable Bonds: 5 |
| Polar Surface Area: 100.90 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.50 | CX Basic pKa: | CX LogP: 4.15 | CX LogD: 4.12 |
| Aromatic Rings: 1 | Heavy Atoms: 25 | QED Weighted: 0.48 | Np Likeness Score: 2.08 |
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. 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] |
Source
Source(1):