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ID: ALA244023
Max Phase: Preclinical
Molecular Formula: C25H28O7
Molecular Weight: 440.49
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): GNF-Pf-98
Synonyms from Alternative Forms(1):
Canonical SMILES: COc1cc(/C=C2\CC/C(=C\c3cc(OC)c(OC)c(OC)c3)C2=O)cc(OC)c1OC
Standard InChI: InChI=1S/C25H28O7/c1-27-19-11-15(12-20(28-2)24(19)31-5)9-17-7-8-18(23(17)26)10-16-13-21(29-3)25(32-6)22(14-16)30-4/h9-14H,7-8H2,1-6H3/b17-9+,18-10+
Standard InChI Key: JKCXONUCRFROOH-BEQMOXJMSA-N
Associated Targets(Human)
HSC-4 439 Activities
HSC-2 771 Activities
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HSC-3 372 Activities
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HL-60 67320 Activities
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Huh-7 12904 Activities
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Estradiol 17-beta-dehydrogenase 3 821 Activities
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Prelamin-A/C 36751 Activities
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Survival motor neuron protein 34246 Activities
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Lysine-specific demethylase 4A 52245 Activities
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ATPase family AAA domain-containing protein 5 122566 Activities
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Importin subunit beta-1/Snurportin-1 25097 Activities
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GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 21853 Activities
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DNA polymerase iota 116820 Activities
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Mothers against decapentaplegic homolog 3 68039 Activities
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PC-3 62116 Activities
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PANC-1 6144 Activities
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HT-29 80576 Activities
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Geminin 128009 Activities
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Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 36611 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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11-beta-hydroxysteroid dehydrogenase 1 5910 Activities
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11-beta-hydroxysteroid dehydrogenase 2 1168 Activities
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Ubiquitin carboxyl-terminal hydrolase 1 22556 Activities
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Parathyroid hormone receptor 47172 Activities
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Associated Targets(non-human)
Plasmodium falciparum 966862 Activities
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Testosterone 17-beta-dehydrogenase 3 232 Activities
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Cruzipain 33337 Activities
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11-beta-hydroxysteroid dehydrogenase 1 202 Activities
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11-beta-hydroxysteroid dehydrogenase 2 82 Activities
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Molecule Features
| Natural Product: No | 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 |
|---|
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: 440.49 | Molecular Weight (Monoisotopic): 440.1835 | AlogP: 4.57 | #Rotatable Bonds: 8 |
| Polar Surface Area: 72.45 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 4.21 | CX LogD: 4.21 |
| Aromatic Rings: 2 | Heavy Atoms: 32 | QED Weighted: 0.56 | Np Likeness Score: 0.02 |
References
| 1. Das U, Kawase M, Sakagami H, Ideo A, Shimada J, Molnár J, Baráth Z, Bata Z, Dimmock JR.. (2007) 3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: a novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity., 15 (10): [PMID:17383883] [10.1016/j.bmc.2007.03.022] |
| 2. Liang G, Shao L, Wang Y, Zhao C, Chu Y, Xiao J, Zhao Y, Li X, Yang S.. (2009) Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents., 17 (6): [PMID:19243951] [10.1016/j.bmc.2008.10.044] |
| 3. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA.. (2008) In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen., 105 (26): [PMID:18579783] [10.1073/pnas.0802982105] |
| 4. Hu GX, Liang G, Chu Y, Li X, Lian QQ, Lin H, He Y, Huang Y, Hardy DO, Ge RS.. (2010) Curcumin derivatives inhibit testicular 17beta-hydroxysteroid dehydrogenase 3., 20 (8): [PMID:20346654] [10.1016/j.bmcl.2010.02.089] |
| 5. PubChem BioAssay data set, |
| 6. Wei X, Du ZY, Zheng X, Cui XX, Conney AH, Zhang K.. (2012) Synthesis and evaluation of curcumin-related compounds for anticancer activity., 53 [PMID:22551677] [10.1016/j.ejmech.2012.04.005] |
| 7. Lin H, Hu GX, Guo J, Ge Y, Liang G, Lian QQ, Chu Y, Yuan X, Huang P, Ge RS.. (2013) Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors., 23 (15): [PMID:23800686] [10.1016/j.bmcl.2013.05.080] |
Source
Source(3):