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ID: ALA131982
Max Phase: Preclinical
Molecular Formula: C18H18O4
Molecular Weight: 298.34
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(/C=C/c1ccc(O)c(O)c1)OCCCc1ccccc1
Standard InChI: InChI=1S/C18H18O4/c19-16-10-8-15(13-17(16)20)9-11-18(21)22-12-4-7-14-5-2-1-3-6-14/h1-3,5-6,8-11,13,19-20H,4,7,12H2/b11-9+
Standard InChI Key: RUTDTHOYUUOTNF-PKNBQFBNSA-N
Associated Targets(Human)
MDA-N 28205 Activities
NCI-H23 49055 Activities
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SN12C 47755 Activities
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ACHN 49357 Activities
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UO-31 46270 Activities
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HL-60 67320 Activities
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HOP-92 41141 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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A498 42825 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-5 45555 Activities
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SNB-19 46794 Activities
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SR 39847 Activities
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MDA-MB-231 73002 Activities
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SW-620 52400 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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OVCAR-4 44535 Activities
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LOX IMVI 44321 Activities
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SK-MEL-2 46422 Activities
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A549 127892 Activities
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HCC 2998 41480 Activities
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HCT-15 51914 Activities
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SF-268 49410 Activities
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HCT-116 91556 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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NCI-H460 60772 Activities
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UACC-62 47335 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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Hs-578T 29457 Activities
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IGROV-1 47897 Activities
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786-0 47912 Activities
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UACC-257 46019 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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LNCaP 8286 Activities
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B cell 126 Activities
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JJN-3 67 Activities
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Associated Targets(non-human)
Human immunodeficiency virus type 1 integrase 9041 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: 298.34 | Molecular Weight (Monoisotopic): 298.1205 | AlogP: 3.29 | #Rotatable Bonds: 6 |
| Polar Surface Area: 66.76 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.21 | CX Basic pKa: | CX LogP: 4.37 | CX LogD: 4.36 |
| Aromatic Rings: 2 | Heavy Atoms: 22 | QED Weighted: 0.37 | Np Likeness Score: 0.59 |
References
| 1. Burke TR, Fesen MR, Mazumder A, Wang J, Carothers AM, Grunberger D, Driscoll J, Kohn K, Pommier Y.. (1995) Hydroxylated aromatic inhibitors of HIV-1 integrase., 38 (21): [PMID:7473544] [10.1021/jm00021a006] |
| 2. Buolamwini JK, Assefa H.. (2002) CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: exploration of a binding mode at the active site., 45 (4): [PMID:11831895] [10.1021/jm010399h] |
| 3. PubChem BioAssay data set, |
| 4. Sanderson JT, Clabault H, Patton C, Lassalle-Claux G, Jean-François J, Paré AF, Hébert MJ, Surette ME, Touaibia M.. (2013) Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells., 21 (22): [PMID:24080105] [10.1016/j.bmc.2013.08.057] |
| 5. Murugesan A,Lassalle-Claux G,Hogan L,Vaillancourt E,Selka A,Luiker K,Kim MJ,Touaibia M,Reiman T. (2020) Antimyeloma Potential of Caffeic Acid Phenethyl Ester and Its Analogues through Sp1 Mediated Downregulation of IKZF1-IRF4-MYC Axis., 83 (12.0): [PMID:33210536] [10.1021/acs.jnatprod.0c00350] |
Source
Source(2):