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ID: ALA309016
Max Phase: Preclinical
Molecular Formula: C9H9NO4
Molecular Weight: 195.17
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc(/C=C/[N+](=O)[O-])ccc1O
Standard InChI: InChI=1S/C9H9NO4/c1-14-9-6-7(2-3-8(9)11)4-5-10(12)13/h2-6,11H,1H3/b5-4+
Standard InChI Key: XVXCSPJSXIUNQJ-SNAWJCMRSA-N
Associated Targets(Human)
Epidermal growth factor receptor erbB1 33727 Activities
Tyrosine-protein kinase ABL 162 Activities
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Tyrosine-protein kinase SYK 7372 Activities
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BXPC-3 2997 Activities
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|---|
MCF7 126967 Activities
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|---|
SF-295 48000 Activities
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|---|
SF-268 49410 Activities
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|---|
NCI-H460 60772 Activities
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|---|
KM-20L2 14967 Activities
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|---|
DU-145 51482 Activities
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|---|
SK-MEL-5 47095 Activities
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|---|
OVCAR-3 48710 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
A498 42825 Activities
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|---|
MDA-MB-231 73002 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
HBL-100 746 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Prelamin-A/C 36751 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Huntingtin 19182 Activities
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|---|
microRNA 21 64692 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Survival motor neuron protein 34246 Activities
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|---|
BJ 6930 Activities
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|---|
Microtubule-associated protein tau 95507 Activities
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|---|
Aldehyde dehydrogenase 1A1 77053 Activities
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|---|
Galanin receptor 2 360 Activities
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|---|
MAP kinase ERK2 25055 Activities
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|---|
Neuropeptide S receptor 15785 Activities
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|---|
Lysine-specific demethylase 4A 52245 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Nuclear factor erythroid 2-related factor 2 95332 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 93046 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Bromodomain adjacent to zinc finger domain protein 2B 56204 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
ATPase family AAA domain-containing protein 5 122566 Activities
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|---|
Vitamin D receptor 26531 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Chromobox protein homolog 1 92434 Activities
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|---|
Flap endonuclease 1 12055 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
DNA polymerase iota 116820 Activities
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|---|
HepG2 196354 Activities
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|---|
Regulator of G-protein signaling 4 13867 Activities
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|---|
Mothers against decapentaplegic homolog 3 68039 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Geminin 128009 Activities
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|---|
DNA dC->dU-editing enzyme APOBEC-3G 12481 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Ataxin-2 54410 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Glucagon-like peptide 1 receptor 111429 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Tyrosyl-DNA phosphodiesterase 1 345557 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
TAR DNA-binding protein 43 40113 Activities
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|---|
Alpha-synuclein 10960 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Isocitrate dehydrogenase [NADP] cytoplasmic 40980 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Serine/threonine-protein kinase PLK1 28605 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Transitional endoplasmic reticulum ATPase 895 Activities
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|---|
Associated Targets(non-human)
P388 20296 Activities
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|---|
Candida albicans 78123 Activities
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|---|
Cryptococcus neoformans 21258 Activities
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|---|
Staphylococcus aureus 210822 Activities
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|---|
Streptococcus pneumoniae 31063 Activities
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|---|
Enterococcus faecalis 29875 Activities
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|---|
Micrococcus luteus 7463 Activities
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|---|
Stenotrophomonas maltophilia 1743 Activities
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|---|
Escherichia coli 133304 Activities
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|---|
Enterobacter cloacae 7976 Activities
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|---|
Neisseria gonorrhoeae 1461 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Nuclear receptor ROR-gamma 89407 Activities
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|---|
Thioredoxin glutathione reductase 28579 Activities
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|---|
4'-phosphopantetheinyl transferase ffp 24982 Activities
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|---|
Inositol monophosphatase 1 16203 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Nonstructural protein 1 33327 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Putative fructose-1,6-bisphosphate aldolase 15559 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
60S ribosomal protein L19-A 106 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Heat shock factor protein 1 5445 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Plasmodium falciparum 966862 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Thioredoxin reductase 1, cytoplasmic 45279 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Luciferin 4-monooxygenase 66902 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Beta Lactamase 819 Activities
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|---|
Aberrant vpr protein 14595 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 |
|---|
Properties
| Molecular Weight: 195.17 | Molecular Weight (Monoisotopic): 195.0532 | AlogP: 1.65 | #Rotatable Bonds: 3 |
| Polar Surface Area: 72.60 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 8.95 | CX Basic pKa: | CX LogP: 1.68 | CX LogD: 1.66 |
| Aromatic Rings: 1 | Heavy Atoms: 14 | QED Weighted: 0.59 | Np Likeness Score: 0.66 |
References
| 1. Traxler PM, Wacker O, Bach HL, Geissler JF, Kump W, Meyer T, Regenass U, Roesel JL, Lydon N.. (1991) Sulfonylbenzoyl-nitrostyrenes: potential bisubstrate type inhibitors of the EGF-receptor tyrosine protein kinase., 34 (8): [PMID:1652014] [10.1021/jm00112a003] |
| 2. Xie HZ, Li LL, Ren JX, Zou J, Yang L, Wei YQ, Yang SY.. (2009) Pharmacophore modeling study based on known spleen tyrosine kinase inhibitors together with virtual screening for identifying novel inhibitors., 19 (7): [PMID:19254842] [10.1016/j.bmcl.2009.02.049] |
| 3. Chang CJ, Geahlen RL.. (1992) Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents., 55 (11): [PMID:1479375] [10.1021/np50089a001] |
| 4. Pettit RK, Pettit GR, Hamel E, Hogan F, Moser BR, Wolf S, Pon S, Chapuis JC, Schmidt JM.. (2009) E-Combretastatin and E-resveratrol structural modifications: antimicrobial and cancer cell growth inhibitory beta-E-nitrostyrenes., 17 (18): [PMID:19709889] [10.1016/j.bmc.2009.07.076] |
| 5. Hsieh PW, Chang YT, Chuang WY, Shih HC, Chiang SZ, Wu CC.. (2010) The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes., 18 (21): [PMID:20850977] [10.1016/j.bmc.2010.08.039] |
| 6. PubChem BioAssay data set, |
| 7. Zhang G,Li S,Wang F,Jones AC,Goldberg AFG,Lin B,Virgil S,Stoltz BM,Deshaies RJ,Chou TF. (2021) A covalent p97/VCP ATPase inhibitor can overcome resistance to CB-5083 and NMS-873 in colorectal cancer cells., 213 [PMID:33476933] [10.1016/j.ejmech.2020.113148] |
Source
Source(2):