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ID: ALA1565145
Max Phase: Preclinical
Molecular Formula: C20H23NO6
Molecular Weight: 373.41
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): NSC-368252
Synonyms from Alternative Forms(1):
Canonical SMILES: COc1ccc(C(c2cc3c(cc2O)OCO3)N2CCOCC2)cc1OC
Standard InChI: InChI=1S/C20H23NO6/c1-23-16-4-3-13(9-17(16)24-2)20(21-5-7-25-8-6-21)14-10-18-19(11-15(14)22)27-12-26-18/h3-4,9-11,20,22H,5-8,12H2,1-2H3
Standard InChI Key: POUGOEFZYGQTHG-UHFFFAOYSA-N
Associated Targets(Human)
Mothers against decapentaplegic homolog 3 68039 Activities
SN12C 47755 Activities
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NCI-H23 49055 Activities
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ACHN 49357 Activities
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UO-31 46270 Activities
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HOP-92 41141 Activities
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HL-60 67320 Activities
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DU-145 51482 Activities
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SF-539 44845 Activities
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Malme-3M 44254 Activities
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SK-MEL-5 47095 Activities
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K562 73714 Activities
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OVCAR-3 48710 Activities
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HOP-62 47048 Activities
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MOLT-4 49676 Activities
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NCI/ADR-RES 33767 Activities
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U-251 51189 Activities
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OVCAR-8 47708 Activities
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OVCAR-5 45555 Activities
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MDA-MB-231 73002 Activities
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SNB-19 46794 Activities
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TK-10 45540 Activities
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SR 39847 Activities
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SW-620 52400 Activities
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KM12 47707 Activities
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NCI-H522 44358 Activities
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M14 47487 Activities
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RPMI-8226 44974 Activities
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NCI-H322M 45589 Activities
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OVCAR-4 44535 Activities
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LOX IMVI 44321 Activities
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BT-549 31254 Activities
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SK-MEL-2 46422 Activities
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A549 127892 Activities
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SNB-75 44215 Activities
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HCT-116 91556 Activities
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HCT-15 51914 Activities
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SF-268 49410 Activities
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MCF7 126967 Activities
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EKVX 44102 Activities
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PC-3 62116 Activities
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SK-OV-3 52876 Activities
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T47D 39041 Activities
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UACC-62 47335 Activities
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NCI-H460 60772 Activities
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CAKI-1 44928 Activities
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MDA-MB-435 38290 Activities
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SF-295 48000 Activities
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IGROV-1 47897 Activities
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Hs-578T 29457 Activities
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UACC-257 46019 Activities
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786-0 47912 Activities
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CCRF-CEM 65223 Activities
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NCI-H226 44470 Activities
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HT-29 80576 Activities
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SK-MEL-28 48833 Activities
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RXF 393 41971 Activities
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COLO 205 50209 Activities
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Protein disulfide-isomerase 716 Activities
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U-87 MG 3946 Activities
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MIA PaCa-2 5949 Activities
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Protein disulfide-isomerase A2 3 Activities
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Protein disulfide-isomerase A3 22 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: 373.41 | Molecular Weight (Monoisotopic): 373.1525 | AlogP: 2.56 | #Rotatable Bonds: 5 |
| Polar Surface Area: 69.62 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.93 | CX Basic pKa: 6.22 | CX LogP: 2.48 | CX LogD: 2.44 |
| Aromatic Rings: 2 | Heavy Atoms: 27 | QED Weighted: 0.86 | Np Likeness Score: -0.34 |
References
| 1. PubChem BioAssay data set, |
| 2. PubChem BioAssay data set, |
| 3. Lavecchia A, Di Giovanni C, Cerchia C, Russo A, Russo G, Novellino E.. (2013) Discovery of a novel small molecule inhibitor targeting the frataxin/ubiquitin interaction via structure-based virtual screening and bioassays., 56 (7): [PMID:23506486] [10.1021/jm3017199] |
| 4. Shergalis A,Xue D,Gharbia FZ,Driks H,Shrestha B,Tanweer A,Cromer K,Ljungman M,Neamati N. (2020) Characterization of Aminobenzylphenols as Protein Disulfide Isomerase Inhibitors in Glioblastoma Cell Lines., 63 (18): [PMID:32830969] [10.1021/acs.jmedchem.0c00728] |
Source
Source(2):