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TUBULOSINE
ID: ALA518568
Max Phase: Preclinical
Molecular Formula: C29H37N3O3
Molecular Weight: 475.63
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Tubulosine
Synonyms from Alternative Forms(1):
Canonical SMILES: CC[C@H]1CN2CCc3cc(OC)c(OC)cc3[C@@H]2C[C@@H]1C[C@H]1NCCc2c1[nH]c1ccc(O)cc21
Standard InChI: InChI=1S/C29H37N3O3/c1-4-17-16-32-10-8-18-13-27(34-2)28(35-3)15-22(18)26(32)12-19(17)11-25-29-21(7-9-30-25)23-14-20(33)5-6-24(23)31-29/h5-6,13-15,17,19,25-26,30-31,33H,4,7-12,16H2,1-3H3/t17-,19-,25+,26-/m0/s1
Standard InChI Key: JRVWIILYWSBUMC-PRUVNFMMSA-N
Associated Targets(Human)
A549 127892 Activities
MCF7 126967 Activities
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HT-29 80576 Activities
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Lu1 576 Activities
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Col2 437 Activities
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KB 17409 Activities
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LNCaP 8286 Activities
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SW626 166 Activities
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SK-N-SH 1499 Activities
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Janus Kinase (JAK) 173 Activities
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MAP kinase p38 1586 Activities
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SN12C 47755 Activities
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MDA-N 28205 Activities
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ACHN 49357 Activities
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NCI-H23 49055 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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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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NCI/ADR-RES 33767 Activities
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HOP-62 47048 Activities
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U-251 51189 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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MDA-MB-231 73002 Activities
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SR 39847 Activities
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TK-10 45540 Activities
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SW-620 52400 Activities
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M19-MEL 15326 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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NCI-H322M 45589 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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BT-549 31254 Activities
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KM-20L2 14967 Activities
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SK-MEL-2 46422 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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HCT-116 91556 Activities
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EKVX 44102 Activities
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SF-268 49410 Activities
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PC-3 62116 Activities
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SK-OV-3 52876 Activities
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LXFL 529 14112 Activities
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DMS-114 15429 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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786-0 47912 Activities
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RXF 631 11415 Activities
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Hs-578T 29457 Activities
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UACC-257 46019 Activities
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SNB-78 14240 Activities
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DLD-1 17511 Activities
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CCRF-CEM 65223 Activities
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NCI-H226 44470 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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HOP-18 11577 Activities
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SN12K1 1050 Activities
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HeLa 62764 Activities
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Associated Targets(non-human)
Artemia 698 Activities
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Agrobacterium tumefaciens 620 Activities
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Human immunodeficiency virus type 1 reverse transcriptase 18245 Activities
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L1210 27553 Activities
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P388 20296 Activities
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M109 194 Activities
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P388/ADR 1216 Activities
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Entamoeba histolytica 2676 Activities
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Acinetobacter baumannii 41033 Activities
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Escherichia coli 133304 Activities
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Pseudomonas aeruginosa 123386 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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Klebsiella pneumoniae 43867 Activities
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Molecule Features
| Natural Product: Yes | 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: 475.63 | Molecular Weight (Monoisotopic): 475.2835 | AlogP: 5.11 | #Rotatable Bonds: 5 |
| Polar Surface Area: 69.75 | Molecular Species: BASE | HBA: 5 | HBD: 3 |
| #RO5 Violations: 1 | HBA (Lipinski): 6 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 9.80 | CX Basic pKa: 9.24 | CX LogP: 3.86 | CX LogD: 1.27 |
| Aromatic Rings: 3 | Heavy Atoms: 35 | QED Weighted: 0.48 | Np Likeness Score: 1.20 |
References
| 1. Ma WW, Anderson JE, McKenzie AT, Byrn SR, McLaughlin JL, Hudson MS.. (1990) Tubulosine: an antitumor constituent of Pogonopus speciosus., 53 (4): [PMID:1982768] [10.1021/np50070a041] |
| 2. Ito A, Lee YH, Chai HB, Gupta MP, Farnsworth NR, Cordell GA, Pezzuto JM, Kinghorn AD.. (1999) 1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus., 62 (9): [PMID:10514334] [10.1021/np990255u] |
| 3. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH.. (1991) Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase., 54 (1): [PMID:1710653] [10.1021/np50073a012] |
| 4. Krutzik PO, Crane JM, Clutter MR, Nolan GP.. (2008) High-content single-cell drug screening with phosphospecific flow cytometry., 4 (2): [PMID:18157122] [10.1038/nchembio.2007.59] |
| 5. PubChem BioAssay data set, |
| 6. Ramirez-Galicia G, Martinez-Pacheco H, Garduno-Juarez R, Deeb O. (2012) Exploring QSAR of antiamoebic agents of isolated natural products by MLR, ANN, and RTO, 21 (9): [10.1007/s00044-011-9767-1] |
| 7. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Natural Product Set III, [10.6019/CHEMBL4296183] |
| 8. Cai YS, Wang C, Tian C, Sun WT, Chen L, Xiao D, Zhou SY, Qiu G, Yu J, Zhu K, Yang SP.. (2019) Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of Alangium salviifolium and Their Cytotoxicity., 82 (9): [PMID:31513408] [10.1021/acs.jnatprod.9b00670] |
Source
Source(3):