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DICHAPETALIN A
ID: ALA453157
Max Phase: Preclinical
Molecular Formula: C38H48O5
Molecular Weight: 584.80
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: C/C(=C\[C@H]1C[C@@H]([C@@H]2CC[C@]34C[C@]23C=C[C@@H]2[C@@]3(C)CC=C5C[C@@H](c6ccccc6)OC[C@]5(C)[C@@H]3C[C@@H](O)[C@]24C)C(=O)O1)CO
Standard InChI: InChI=1S/C38H48O5/c1-23(20-39)16-26-18-27(33(41)43-26)28-11-15-38-21-37(28,38)14-12-30-34(2)13-10-25-17-29(24-8-6-5-7-9-24)42-22-35(25,3)31(34)19-32(40)36(30,38)4/h5-10,12,14,16,26-32,39-40H,11,13,15,17-22H2,1-4H3/b23-16+/t26-,27-,28-,29-,30+,31+,32+,34+,35-,36-,37+,38+/m0/s1
Standard InChI Key: LRJFCTOUXFAGON-NNLSLSRSSA-N
Associated Targets(Human)
Lu1 576 Activities
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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MCF7 126967 Activities
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HUVEC 11049 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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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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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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MDA-MB-231 73002 Activities
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SNB-19 46794 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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NCI-H522 44358 Activities
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KM12 47707 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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SK-MEL-2 46422 Activities
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HCC 2998 41480 Activities
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A549 127892 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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SF-268 49410 Activities
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PC-3 62116 Activities
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EKVX 44102 Activities
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SK-OV-3 52876 Activities
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NCI-H460 60772 Activities
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T47D 39041 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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Hs-578T 29457 Activities
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UACC-257 46019 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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HT-29 80576 Activities
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RXF 393 41971 Activities
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COLO 205 50209 Activities
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Acetylcholinesterase 18204 Activities
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Jurkat 10389 Activities
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WM 266-4 208 Activities
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Associated Targets(non-human)
L1210 27553 Activities
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Spodoptera exigua 540 Activities
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Panagrellus redivivus 38 Activities
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Colletotrichum gloeosporioides 560 Activities
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Fusarium oxysporum f. sp. niveum 47 Activities
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Rhizoctonia solani 2251 Activities
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RAW264.7 28094 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: 584.80 | Molecular Weight (Monoisotopic): 584.3502 | AlogP: 6.72 | #Rotatable Bonds: 4 |
| Polar Surface Area: 75.99 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 2 |
| #RO5 Violations: 2 | HBA (Lipinski): 5 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 4.83 | CX LogD: 4.83 |
| Aromatic Rings: 1 | Heavy Atoms: 43 | QED Weighted: 0.30 | Np Likeness Score: 3.29 |
References
| 1. Tuchinda P, Kornsakulkarn J, Pohmakotr M, Kongsaeree P, Prabpai S, Yoosook C, Kasisit J, Napaswad C, Sophasan S, Reutrakul V.. (2008) Dichapetalin-type triterpenoids and lignans from the aerial parts of Phyllanthus acutissima., 71 (4): [PMID:18271551] [10.1021/np7007347] |
| 2. Fang L, Ito A, Chai HB, Mi Q, Jones WP, Madulid DR, Oliveros MB, Gao Q, Orjala J, Farnsworth NR, Soejarto DD, Cordell GA, Swanson SM, Pezzuto JM, Kinghorn AD.. (2006) Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collected in the Philippines., 69 (3): [PMID:16562829] [10.1021/np058083q] |
| 3. PubChem BioAssay data set, |
| 4. Jing SX, Luo SH, Li CH, Hua J, Wang YL, Niu XM, Li XN, Liu Y, Huang CS, Wang Y, Li SH.. (2014) Biologically active dichapetalins from Dichapetalum gelonioides., 77 (4): [PMID:24597894] [10.1021/np400971r] |
| 5. Ren Y,Kinghorn AD. (2020) Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones., 63 (24.0): [PMID:33289552] [10.1021/acs.jmedchem.0c01449] |
Source
Source(2):