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ID: ALA460900
Max Phase: Preclinical
Molecular Formula: C26H30ClNO4
Molecular Weight: 420.53
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCCCCCc1c2[n+](cc3c(OC)c(OC)ccc13)CCc1cc3c(cc1-2)OCO3.[Cl-]
Standard InChI: InChI=1S/C26H30NO4.ClH/c1-4-5-6-7-8-19-18-9-10-22(28-2)26(29-3)21(18)15-27-12-11-17-13-23-24(31-16-30-23)14-20(17)25(19)27;/h9-10,13-15H,4-8,11-12,16H2,1-3H3;1H/q+1;/p-1
Standard InChI Key: LLJCPAIRNFYCCE-UHFFFAOYSA-M
Associated Targets(Human)
St-4 163 Activities
MKN-74 303 Activities
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MKN-45 2102 Activities
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MKN-28 466 Activities
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MKN-7 272 Activities
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SNB-78 14240 Activities
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SNB-75 44215 Activities
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SF-268 49410 Activities
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SF-539 44845 Activities
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SF-295 48000 Activities
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U-251 51189 Activities
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LOX IMVI 44321 Activities
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ACHN 49357 Activities
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MCF7 126967 Activities
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SK-OV-3 52876 Activities
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OVCAR-8 47708 Activities
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OVCAR-5 45555 Activities
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OVCAR-4 44535 Activities
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OVCAR-3 48710 Activities
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HCT-116 91556 Activities
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HCT-15 51914 Activities
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WiDr 1835 Activities
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HT-29 80576 Activities
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KM12 47707 Activities
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HCC 2998 41480 Activities
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A549 127892 Activities
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DMS-114 15429 Activities
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DMS-273 14108 Activities
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NCI-H460 60772 Activities
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NCI-H522 44358 Activities
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NCI-H226 44470 Activities
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NCI-H23 49055 Activities
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MDA-MB-231 73002 Activities
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HL-60 67320 Activities
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HepG2 196354 Activities
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Associated Targets(non-human)
Mycobacterium tuberculosis 203094 Activities
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Lemna minor 73 Activities
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Agrostis stolonifera var. palustris 53 Activities
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Ustilago maydis 75 Activities
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Phytophthora infestans 820 Activities
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Rhizoctonia solani 2251 Activities
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Pyricularia oryzae 1832 Activities
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Zymoseptoria tritici 367 Activities
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Parastagonospora nodorum 325 Activities
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Puccinia recondita 281 Activities
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Blumeria graminis f. sp. tritici 444 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 |
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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: 420.53 | Molecular Weight (Monoisotopic): 420.2169 | AlogP: 5.22 | #Rotatable Bonds: 7 |
| Polar Surface Area: 40.80 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 0 |
| #RO5 Violations: 1 | HBA (Lipinski): 5 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 1.45 | CX LogD: 1.45 |
| Aromatic Rings: 3 | Heavy Atoms: 31 | QED Weighted: 0.39 | Np Likeness Score: 1.20 |
References
| 1. Li YH, Yang P, Kong WJ, Wang YX, Hu CQ, Zuo ZY, Wang YM, Gao H, Gao LM, Feng YC, Du NN, Liu Y, Song DQ, Jiang JD.. (2009) Berberine analogues as a novel class of the low-density-lipoprotein receptor up-regulators: synthesis, structure-activity relationships, and cholesterol-lowering efficacy., 52 (2): [PMID:19090767] [10.1021/jm801157z] |
| 2. Iwasa K, Moriyasu M, Yamori T, Turuo T, Lee DU, Wiegrebe W.. (2001) In vitro cytotoxicity of the protoberberine-type alkaloids., 64 (7): [PMID:11473418] [10.1021/np000554f] |
| 3. Liu YX, Xiao CL, Wang YX, Li YH, Yang YH, Li YB, Bi CW, Gao LM, Jiang JD, Song DQ.. (2012) Synthesis, structure-activity relationship and in vitro anti-mycobacterial evaluation of 13-n-octylberberine derivatives., 52 [PMID:22503208] [10.1016/j.ejmech.2012.03.012] |
| 4. Iwasa K, Moriyasu M, Nader B.. (2000) Fungicidal and herbicidal activities of berberine related alkaloids., 64 (9): [PMID:11055412] [10.1271/bbb.64.1998] |
Source
Source(1):