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ID: ALA63647
Max Phase: Preclinical
Molecular Formula: C10H13N3O4
Molecular Weight: 239.23
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Nc1ccn([C@@H]2C=C(CO)[C@@H](O)[C@H]2O)c(=O)n1
Standard InChI: InChI=1S/C10H13N3O4/c11-7-1-2-13(10(17)12-7)6-3-5(4-14)8(15)9(6)16/h1-3,6,8-9,14-16H,4H2,(H2,11,12,17)/t6-,8-,9+/m1/s1
Standard InChI Key: DUJGMZAICVPCBJ-VDAHYXPESA-N
Associated Targets(Human)
CCRF-CEM 65223 Activities
SN12C 47755 Activities
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MDA-N 28205 Activities
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NCI-H23 49055 Activities
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UO-31 46270 Activities
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ACHN 49357 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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SK-MEL-5 47095 Activities
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Malme-3M 44254 Activities
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A498 42825 Activities
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K562 73714 Activities
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OVCAR-3 48710 Activities
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MOLT-4 49676 Activities
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HOP-62 47048 Activities
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U-251 51189 Activities
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NCI/ADR-RES 33767 Activities
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OVCAR-5 45555 Activities
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OVCAR-8 47708 Activities
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DMS-273 14108 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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M19-MEL 15326 Activities
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TK-10 45540 Activities
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NCI-H522 44358 Activities
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KM12 47707 Activities
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XF498 12972 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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KM-20L2 14967 Activities
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HCC 2998 41480 Activities
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SNB-75 44215 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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EKVX 44102 Activities
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MCF7 126967 Activities
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DMS-114 15429 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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MDA-MB-435 38290 Activities
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CAKI-1 44928 Activities
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IGROV-1 47897 Activities
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SF-295 48000 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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SNB-78 14240 Activities
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DLD-1 17511 Activities
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NCI-H226 44470 Activities
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SK-MEL-28 48833 Activities
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HT-29 80576 Activities
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RXF 393 41971 Activities
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COLO 205 50209 Activities
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SN12K1 1050 Activities
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HOP-18 11577 Activities
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Associated Targets(non-human)
L1210 27553 Activities
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Uridine-cytidine kinase 1 5 Activities
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Vero 26788 Activities
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Human immunodeficiency virus 1 70413 Activities
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West Nile virus 623 Activities
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P388 20296 Activities
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M5076 114 Activities
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Mus musculus 284745 Activities
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Cytomegalovirus 1023 Activities
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Human alphaherpesvirus 3 4092 Activities
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Vesicular stomatitis virus 4460 Activities
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Yellow fever virus 1530 Activities
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Japanese encephalitis virus 187 Activities
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Punta Toro virus 1491 Activities
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unidentified influenza virus 265 Activities
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P388/ADR 1216 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 |
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Properties
| Molecular Weight: 239.23 | Molecular Weight (Monoisotopic): 239.0906 | AlogP: -1.98 | #Rotatable Bonds: 2 |
| Polar Surface Area: 121.60 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 5 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 13.16 | CX Basic pKa: | CX LogP: -2.90 | CX LogD: -2.90 |
| Aromatic Rings: 1 | Heavy Atoms: 17 | QED Weighted: 0.44 | Np Likeness Score: 1.38 |
References
| 1. Chu CK, Jin YH, Baker RO, Huggins J.. (2003) Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox)., 13 (1): [PMID:12467606] [10.1016/s0960-894x(02)00841-7] |
| 2. Lim MI, Moyer JD, Cysyk RI, Marquez VE.. (1984) Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase., 27 (12): [PMID:6094806] [10.1021/jm00378a002] |
| 3. Marquez VE, Lim MI, Treanor SP, Plowman J, Priest MA, Markovac A, Khan MS, Kaskar B, Driscoll JS.. (1988) Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties., 31 (9): [PMID:3411597] [10.1021/jm00117a004] |
| 4. Copp RR, Marquez VE.. (1991) Synthesis of two cyclopentenyl-3-deazapyrimidine carbocyclic nucleosides related to cytidine and uridine., 34 (1): [PMID:1992119] [10.1021/jm00105a032] |
| 5. Song GY, Paul V, Choo H, Morrey J, Sidwell RW, Schinazi RF, Chu CK.. (2001) Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus., 44 (23): [PMID:11689085] [10.1021/jm010256v] |
| 6. PubChem BioAssay data set, |
Source
Source(2):