Synonym
Datiscoside; NSC144153; NSC-144153; NSC 144153
IUPAC/Chemical Name
(10alpha)-16alpha-((2-O-Acetyl-6-deoxy-alpha-L-ribo-hexopyranos-3-ulos-1-yl)oxy)-2beta,20,25-trihydroxy-9beta-methyl-19-norlanosta-5,23(E)-diene-3,11,22-trione
InChi Key
UDPKVFLHNMOFJY-NOLRCJNXSA-N
InChi Code
InChI=1S/C38H54O13/c1-18-27(43)28(44)31(49-19(2)39)38(48,50-18)51-23-16-34(7)24-12-11-20-21(15-22(40)30(45)33(20,5)6)36(24,9)26(42)17-35(34,8)29(23)37(10,47)25(41)13-14-32(3,4)46/h11,13-14,18,21-24,27,29,31,40,43,46-48H,12,15-17H2,1-10H3/b14-13+/t18-,21+,22-,23+,24-,27-,29-,31-,34-,35+,36-,37-,38-/m0/s1
SMILES Code
CC(C)(C1=CC[C@@]2([H])[C@@]3(C[C@@H](O[C@]([C@H]4OC(C)=O)(O[C@@H](C)[C@@H](C4=O)O)O)[C@@H]([C@]3(C5)C)[C@@](C)(O)C(/C=C/C(C)(O)C)=O)C)C([C@@H](O)C[C@@]1([H])[C@]2(C)C5=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
|
Solvent |
mg/mL |
mM |
| Solubility |
| Soluble in DMSO |
0.0 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
718.84
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Kupchan SM, Sigel CW, Guttman LJ, Restivo RJ, Bryan RF. Datiscoside, a novel antileukemic cucurbitacin glycoside from Datisca glomerata. J Am Chem Soc. 1972 Feb 23;94(4):1353-4. doi: 10.1021/ja00759a053. PMID: 5060279.
2: Graziose R, Grace MH, Rathinasabapathy T, Rojas-Silva P, Dekock C, Poulev A, Lila MA, Smith P, Raskin I. Antiplasmodial activity of cucurbitacin glycosides from Datisca glomerata (C. Presl) Baill. Phytochemistry. 2013 Mar;87:78-85. doi: 10.1016/j.phytochem.2012.11.025. Epub 2012 Dec 25. PMID: 23270868.
3: Ficarra R, Ficarra P, Tommasini S, Calabrò ML, Ragusa S, Barbera R, Rapisarda A. Leaf extracts of some Cordia species: analgesic and anti-inflammatory activities as well as their chromatographic analysis. Farmaco. 1995 Apr;50(4):245-56. PMID: 7669169.
4: Smythies JR. On the molecular structure of some prostaglandin receptors. Prostaglandins Med. 1979 May;2(5):393-400. doi: 10.1016/0161-4630(79)90112-5. PMID: 233033.
