acivicin
AlkaPlorer ID: AK010896
Synonym: 'SMR000058744', 'ACIVICIN', 'MLSMR', 'MLS000028629', 'Acivicin'
IUPAC Name: (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
Structure
SMILES: N[C@H](C(=O)O)[C@@H]1CC(Cl)=NO1
InChI: InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1
InChIKey: QAWIHIJWNYOLBE-OKKQSCSOSA-N
Reference
Acivicin (AT125, U42126): Isolation and structure of an alkali-induced contaminant.
PubChem CID: 40467943
LOTUS: LTS0145898
SuperNatural Ⅲ: SN0300396-03
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Streptomyces sviceus | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
Properties Information
Molecule Weight: 178.575
TPSA？: 84.91000000000001
MolLogP？: -0.2604999999999999
Number of H-Donors: 2
Number of H-Acceptors: 4
RingCount: 1
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Electrophorus electricus | Acetylcholinesterase | Inhibition | 2.09 | % | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Cholinesterase | Inhibition | 8.62 | % | 10.1016/j.bmc.2012.09.040 |
| Homo sapiens | 786-0 | GI50 | 13803.84 | nM | None |
| Homo sapiens | A498 | GI50 | 6839.12 | nM | None |
| Homo sapiens | A549 | GI50 | 916.22 | nM | None |
| Homo sapiens | ACHN | GI50 | 1465.55 | nM | None |
| Homo sapiens | Bromodomain-containing protein 4 | Delta TM | -0.13 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | BT-549 | GI50 | 42953.64 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 2523.48 | nM | None |
| Homo sapiens | Casein kinase I delta | Delta TM | 0.22 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | CCRF-CEM | GI50 | 1191.24 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 5915.62 | nM | None |
| Homo sapiens | Cyclin-dependent kinase 2 | Delta TM | 0.85 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | DLD-1 | GI50 | 1230.27 | nM | None |
| Homo sapiens | DMS-114 | GI50 | 5533.5 | nM | None |
| Homo sapiens | DMS-273 | GI50 | 2328.09 | nM | None |
| Homo sapiens | DU-145 | GI50 | 2477.42 | nM | None |
| Homo sapiens | EKVX | GI50 | 2535.13 | nM | None |
| Homo sapiens | Fibroblast | Growth Rate | -1.0 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | -0.62 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | -0.24 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.08 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.11 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.21 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.22 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.4 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast | Growth Rate | 0.56 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | Fibroblast growth factor receptor 3 | Delta TM | 0.45 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | Gamma-glutamyltranspeptidase 1 | K | 0.4 | /M/s | 10.1016/j.bmc.2013.12.034 |
| Homo sapiens | Glycogen synthase kinase-3 beta | Delta TM | 0.23 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | HCC 2998 | GI50 | 8994.98 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 746.45 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 737.9 | nM | None |
| Homo sapiens | HEK-293T | Growth Rate | 0.17 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | 0.37 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | 0.43 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | 0.51 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | 0.57 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HEK-293T | Growth Rate | 0.69 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | HL-60 | GI50 | 3443.5 | nM | None |
| Homo sapiens | HOP-18 | GI50 | 37931.5 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 1422.33 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 33189.45 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 3622.43 | nM | None |
| Homo sapiens | HT-29 | GI50 | 787.05 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 698.23 | nM | None |
| Homo sapiens | K562 | GI50 | 2460.37 | nM | None |
| Homo sapiens | KM12 | GI50 | 638.26 | nM | None |
| Homo sapiens | KM-20L2 | GI50 | 1361.44 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 1455.46 | nM | None |
| Homo sapiens | M14 | GI50 | 2904.02 | nM | None |
| Homo sapiens | M19-MEL | GI50 | 1629.3 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 4255.98 | nM | None |
| Homo sapiens | MAP kinase ERK2 | Delta TM | 0.14 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | MCF7 | GI50 | 676.08 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 72610.6 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 3899.42 | nM | None |
| Homo sapiens | MDA-N | GI50 | 4064.43 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 2142.89 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 4436.09 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 12161.86 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 4073.8 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 10023.05 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 451.86 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 4425.88 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 2167.7 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 14554.59 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 7709.03 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 2177.71 | nM | None |
| Homo sapiens | PC-3 | GI50 | 1482.52 | nM | None |
| Homo sapiens | Peregrin | Delta TM | -1.19 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | RPMI-8226 | GI50 | 3303.7 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 7620.79 | nM | None |
| Homo sapiens | Serine/threonine-protein kinase Aurora-A | Delta TM | -0.37 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | SF-268 | GI50 | 1534.62 | nM | None |
| Homo sapiens | SF-295 | GI50 | 2290.87 | nM | None |
| Homo sapiens | SF-539 | GI50 | 3556.31 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 4613.18 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 4395.42 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 1986.09 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 12589.25 | nM | None |
| Homo sapiens | SN12C | GI50 | 3499.45 | nM | None |
| Homo sapiens | SN12K1 | GI50 | 1129.8 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 4305.27 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 25882.13 | nM | None |
| Homo sapiens | SNB-78 | GI50 | 4246.2 | nM | None |
| Homo sapiens | Solute carrier organic anion transporter family member 1B1 | Inhibition | 137.66 | % | 10.1124/mol.112.084152 |
| Homo sapiens | Solute carrier organic anion transporter family member 1B3 | Inhibition | 113.31 | % | 10.1124/mol.112.084152 |
| Homo sapiens | SR | GI50 | 739.61 | nM | None |
| Homo sapiens | SW-620 | GI50 | 1069.05 | nM | None |
| Homo sapiens | T47D | GI50 | 7726.81 | nM | None |
| Homo sapiens | TK-10 | GI50 | 2703.96 | nM | None |
| Homo sapiens | Transcription intermediary factor 1-alpha | Delta TM | -0.82 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | Tyrosine-protein kinase ABL | Delta TM | -0.08 | C | 10.6019/CHEMBL5308504 |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 1678.9 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 2113.6 | nM | None |
| Homo sapiens | U-251 | GI50 | 2208.0 | nM | None |
| Homo sapiens | U2OS | Growth Rate | 0.51 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | U2OS | Growth Rate | 0.81 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | U2OS | Growth Rate | 0.99 | None | 10.6019/CHEMBL5303304 |
| Homo sapiens | UACC-257 | GI50 | 4797.33 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 2792.54 | nM | None |
| Homo sapiens | UO-31 | GI50 | 6251.73 | nM | None |
| Homo sapiens | XF498 | GI50 | 23823.19 | nM | None |
| Mus musculus | P388 | GI50 | 241.55 | nM | None |
| Mus musculus | P388/ADR | GI50 | 470.98 | nM | None |
| Plasmodium falciparum | Glyceraldehyde-3-phosphate dehydrogenase | Inhibition | nan | % | 10.1021/jm500747h |
| None | ADMET | CL | 0.69 | mL.min-1.kg-1 | 10.1124/dmd.108.020479 |
| None | ADMET | CL | 0.78 | mL.min-1.kg-1 | 10.1002/jps.20373 |
| None | ADMET | CL | 1.3 | mL.min-1.kg-1 | 10.1002/jps.20373 |
| None | ADMET | CL | 3.3 | mL.min-1.kg-1 | 10.1002/jps.20373 |
| None | ADMET | CL | 5.2 | mL.min-1.kg-1 | 10.1002/jps.20373 |
| None | ADMET | MRT | 12.0 | hr | 10.1124/dmd.108.020479 |
| None | ADMET | T1/2 | 9.9 | hr | 10.1124/dmd.108.020479 |
| None | ADMET | Vdss | 0.5 | L.kg-1 | 10.1002/jps.20373 |
| None | ADMET | Vdss | 0.5 | L.kg-1 | 10.1124/dmd.108.020479 |
| None | ADMET | Vdss | 0.56 | L.kg-1 | 10.1002/jps.20373 |
| None | ADMET | Vdss | 0.58 | L.kg-1 | 10.1002/jps.20373 |
| None | ADMET | Vdss | 0.65 | mL/min/kg | 10.1002/jps.20373 |
| None | Hepatotoxicity | DILI positive/negative | 0.0 | None | 10.1371/journal.pcbi.1002310 |
| None | Hepatotoxicity | Hepatotoxicity | nan | None | 10.1021/tx1000865 |
| None | Hepatotoxicity | Hepatotoxicity | nan | None | 10.1124/dmd.110.035113 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (acute) | 0.0 | % | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (animal toxicity known) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (benign tumour) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (granulomatous hepatitis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (mechanism) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (moderate) | 3.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (moderate) | 62.0 | % | 10.1016/s0399-8320(04)95062-2 |
| None | NON-PROTEIN TARGET | Hepatotoxicity (time to onset) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (acute) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (association with vascular disease) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (choleostasis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (chronic liver disease) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (cirrhosis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (comment) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (cytolytic) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (malignant tumour) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (severe hepatitis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (steatosis) | 0.0 | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Hepatotoxicity (successful reintroduction) | nan | None | 10.1016/s0399-8320(04)95062-2 |
| None | Unchecked | Inhibition | nan | % | 10.1016/j.bmc.2016.08.050 |
| None | Unchecked | K | 4200.0 | /M/s | 10.1016/j.bmc.2013.12.034 |
| None | Unchecked | Potency | 1584.9 | nM | None |
| None | Unchecked | Potency | 1995.3 | nM | None |
| None | Unchecked | Potency | 15848.9 | nM | None |
| None | Unchecked | Potency | 35481.3 | nM | None |