Compound: Protodioscin
SMILES: O1[C@@H](O[C@@H]2CC3=CC[C@H]4[C@H]5[C@]([C@H]6[C@@H]([C@@](O)(CC[C@H](CO[C@@H]7O[C@@H]([C@@H](O)[C@@H]([C@H]7O)O)CO)C)O[C@H]6C5)C)(C)CC[C@@H]4[C@@]3(C)CC2)[C@H](O[C@@H]8O[C@H]([C@H](O)[C@H]([C@H]8O)O)C)[C@@H](O)[C@@H]([C@H]1CO)O[C@@H]9O[C@H]([C@H](O)[C@H]([C@H]9O)O)C
InChIKey: LVTJOONKWUXEFR-UEZXSUPNSA-N
Synonyms: Protodioscin, 55056-80-9, D0LC3PH24P, CHEBI:8588, (3beta,22R,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl alpha-L-rhamnopyranosyl-(1->2)-[alpha-L-rhamnopyranosyl-(1->4)]-beta-D-glucopyranoside, DTXSID901021361, NSC698796, (3beta,22R,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl alpha-L-rhamnopyranosyl-(1->2)-(alpha-L-rhamnopyranosyl-(1->4))-beta-D-glucopyranoside, RefChem:46278, DTXCID201506463, beta-D-Glucopyranoside, (3beta,22beta,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1->4))-, (2S,3R,4R,5R,6S)-2-((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-((3R)-3-methyl-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxybutyl)-5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-en-16-yl)oxy)-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol, Furostanol I, Protodioscin?, MFCD03427682, Furostane base-2H + O-Hex, O-Hex-dHex-dHex, 90288-44-1, UNII-D0LC3PH24P, proto-dioscin, PROTODIOSCINE, Protodioscin (Standard), PROTODIOSCIN [WHO-DD], SCHEMBL786390, orb1305696, orb3140924, CHEMBL4782480, HY-N0799R, EX-A3793, Furost-5-ene-3,22,26-triol 3-chacotrioside-26-glucopyranoside, HY-N0799, s3830, AKOS025311548, CCG-270619, CS-6050, EBC-509148, OP09383, AS-75278, SY231911, NS00123326, C08907, Q7251968, (3b, 25R)-26-(b-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1-2)-O-[6-deoxy-a-L-mannopyranosyl-(1- 4)]-b-D-glucopyranoside, .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-26-(.BETA.-D-GLUCOPYRANOSYLOXY)-22-HYDROXYFUROST-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-, 26-O-.BETA.-D-GLUCOPYRANOSYL-(25R)-FUROST-5-ENE-3.BETA.,22.ALPHA.,26-TRIOL 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-(1-2)-(.ALPHA.-L-RHAMNOPYRANOSYL-(1-4))-.BETA.-D-GLUCOPYRANOSIDE, 3.BETA.,22.ALPHA.,26-TRIHYDROXYFUROST-5-ENE 3-O-.BETA.-CHACOTRIOSIDE 26-O-.BETA.-D-GLUCOPYRANOSIDE, beta-D-Glucopyranoside, (3beta,22alpha)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-, (R-(Z))-
Theoretical properties:
molecular_formula: C51H84O22
molecular_weight: 1049.2 g/mol
exact_mass: 1048.54542430 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 13
hydrogen_bond_acceptor_count: 22
rotatable_bond_count: 14
heavy_atom_count: 73
topological_polar_surface_area: 346 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Protodioscin is a furostanol glycoside that consists of the trisaccharide alpha-L-Rha-(14)-[alpha-L-Rha-(12)]-beta-D-Glc attached to position 3 of 26-(beta-D-glucopyranosyloxy)-3beta,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek. It has a role as an antineoplastic agent, an antilipemic drug, a neuroprotective agent, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is a beta-D-glucoside, a pentacyclic triterpenoid, a cyclic hemiketal, a steroid saponin and a trisaccharide derivative. It derives from a hydride of a furostan.", "chebi": "A furostanol glycoside that consists of the trisaccharide \u03b1-<small>L</small>-Rha-(1\u21924)-[\u03b1-<small>L</small>-Rha-(1\u21922)]-\u03b2-<small>D</small>-Glc attached to position 3 of 26-(\u03b2-<small>D</small>-glucopyranosyloxy)-3\u03b2,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek.", "chembl": "Unnamed Compound is a unknown listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Protodioscin is a steroidal saponin compound found in a number of plant species, most notably in the Tribulus, Trigonella Dioscorea and  Trillium families. It is best known as the putative active component of the herbal aphrodisiac plant Tribulus terrestris.\nExtracts of T. terrestris standardized for protodioscin content have been shown to produce proerectile effects in isolated tissues and aphrodisiac activity in several animal models. Protodioscin is thought to contribute to increased androgen receptor immunoreactivity in some tissues, likely as a secondary effect of elevated levels of endogenous androgens such as testosterone and dihydrotestosterone (DHT). This increase in androgen receptor immunoreactivity has been observed after administration of Tribulus terrestris extracts, but current evidence does not support the view that protodioscin acts primarily or directly by raising the density of androgen receptors; instead, it may enhance androgen receptor expression indirectly through its influence on androgen levels.\nAlthough the precise mechanism has not been fully established, protodioscin has been reported to stimulate the release of nitric oxide in corpus cavernosum tissue, as well as to significantly increase circulating levels of testosterone, dihydrotestosterone, and dehydroepiandrosterone in animal studies. However, clinical studies in humans have not demonstrated consistent efficacy, and the therapeutic value of T. terrestris extracts remains controversial."}