Physicochemical Properties
| Molecular Formula | C45H72O17 |
| Molecular Weight | 885.054 |
| Exact Mass | 884.476 |
| Elemental Analysis | C, 61.07; H, 8.20; O, 30.73 |
| CAS # | 19083-00-2 |
| Related CAS # | 19083-00-2 |
| PubChem CID | 159861 |
| Appearance | Off-white to light yellow solid powder |
| Density | 1.4±0.1 g/cm3 |
| Melting Point | 290-293℃ (DEC.) |
| Index of Refraction | 1.623 |
| LogP | 4.41 |
| Hydrogen Bond Donor Count | 9 |
| Hydrogen Bond Acceptor Count | 17 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 62 |
| Complexity | 1620 |
| Defined Atom Stereocenter Count | 26 |
| SMILES | O1[C@]2(C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O2)C([H])(C([H])([H])[H])[C@]2([H])[C@@]1([H])C([H])([H])[C@]1([H])[C@@]3([H])C([H])([H])C([H])=C4C([H])([H])C([H])(C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])O[C@]1([H])C([H])(C([H])(C([H])(C([H])(C([H])([H])O[H])O1)O[H])O[C@]1([H])C([H])(C([H])(C([H])(C([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])O[C@]1([H])C([H])(C([H])(C([H])(C([H])(C([H])([H])[H])O1)O[H])O[H])O[H] |
| InChi Key | YQEMAEKYNNOCBY-IEMDQPGHSA-N |
| InChi Code | InChI=1S/C45H72O17/c1-19-8-13-45(55-18-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(53)34(51)31(48)21(3)56-40)38(33(50)29(17-47)59-42)60-41-37(54)35(52)32(49)28(16-46)58-41/h6,19-21,23-42,46-54H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33-,34-,35+,36-,37-,38+,39-,40+,41+,42-,43+,44+,45-/m1/s1 |
| Chemical Name | (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol |
| Synonyms | NSC698787; NSC 698787; NSC-698787; Gracillin |
| HS Tariff Code | 2934.99.03.00 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Gracillin has no activity against EKVX (non-small cell lung cancer), HT29 (colon cancer), OVCAR-5 (ovarian cancer), and SN12C (renal cancer), but it is cytotoxic against the majority of cell lines with GI50, TGI, and LC50 at micromolar levels[1]. |
| ln Vivo | Gavage: 10 mg/kg for xenografts; 20 mg/kg for PDX models; Xenografts derived from lung cancers (intestinal and lung tumors) and metamorphic tumors of the enclosed lung (H1299), stent (DU145), and colorectal (HCT116) [1]. Tumor growth in transplanted tumors. |
| References |
[1]. The natural compound gracillin exerts potent antitumor activity by targeting mitochondrial complex II. Cell Death Dis. 2019 Oct 24;10(11):810. [2]. Gracillin Isolated from Reineckia carnea Induces Apoptosis of A549 Cells via the Mitochondrial Pathway. Drug Des Devel Ther. 2021 Jan 20;15:233-243. [3]. Gracillin Shows Potential Efficacy Against Non-Small Cell Lung Cancer Through Inhibiting the mTOR Pathway. Front Oncol. 2022 Mar 22;12:851300. |
| Additional Infomation |
Gracillin is a triterpenoid. Gracillin has been reported in Dioscorea collettii, Dracaena cochinchinensis, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~250 mg/mL (~282.5 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1299 mL | 5.6494 mL | 11.2988 mL | |
| 5 mM | 0.2260 mL | 1.1299 mL | 2.2598 mL | |
| 10 mM | 0.1130 mL | 0.5649 mL | 1.1299 mL |