3beta,6beta,23-Trihydroxyoleana-12-ene-28-oic acid 6-O-(4-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-beta-D-glucopyranosyl ester

Details

• Internal ID: 4d28e437-da49-46d6-b3c1-2889d3db560a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8R,8aR,9R,10S,12aR,14bS)-8,10-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8C(CC7(C6(CC5)C)C)O)(C)CO)O)C)(C)C)O)O)O)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)[C@@]45CC[C@@]6(C(=CC[C@H]7[C@]6(C[C@H]([C@@H]8[C@@]7(CC[C@@H]([C@@]8(C)CO)O)C)O)C)[C@@H]4CC(CC5)(C)C)C)O)O)O)CO)O)O)O
• InChI: InChI=1S/C48H78O19/c1-21-29(53)31(55)34(58)40(63-21)66-37-25(18-49)64-39(36(60)33(37)57)62-19-26-30(54)32(56)35(59)41(65-26)67-42(61)48-14-12-43(2,3)16-23(48)22-8-9-27-44(4)11-10-28(52)45(5,20-50)38(44)24(51)17-47(27,7)46(22,6)13-15-48/h8,21,23-41,49-60H,9-20H2,1-7H3/t21-,23-,24+,25+,26+,27+,28-,29-,30+,31+,32-,33+,34+,35+,36+,37+,38+,39+,40-,41-,44+,45+,46+,47+,48-/m0/s1
• InChI Key: DUQMBNHUHLOXBM-VKJCULEXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₉
• Molecular Weight: 959.10 g/mol
• Exact Mass: 958.51373025 g/mol
• Topological Polar Surface Area (TPSA): 315.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.89
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8883	88.83%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8945	89.45%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8448	84.48%
P-glycoprotein inhibitior	+	0.7423	74.23%
P-glycoprotein substrate	-	0.5251	52.51%
CYP3A4 substrate	+	0.7265	72.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.6840	68.40%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9055	90.55%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7392	73.92%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8952	89.52%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8307	83.07%
Androgen receptor binding	+	0.7456	74.56%
Thyroid receptor binding	-	0.5201	52.01%
Glucocorticoid receptor binding	+	0.7135	71.35%
Aromatase binding	+	0.6612	66.12%
PPAR gamma	+	0.8131	81.31%
Honey bee toxicity	-	0.6545	65.45%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.9411	94.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.93%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.18%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.71%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.71%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.65%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.24%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.19%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.81%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.71%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.54%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.41%	96.77%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.44%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.39%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.68%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.53%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.01%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	82.69%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.04%	97.25%

Plants that contains it

• Achillea clypeolata
• Athanasia crithmifolia
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Centella asiatica
• Cerbera odollam
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Crateva magna
• Diospyros verrucosa
• Euonymus nanoides
• Jacobaea subalpina
• Nepeta multifida
• Pleogyne australis
• Polygala amara
• Pyrola decorata
• Quercus serrata
• Rubus allegheniensis
• Salvia abrotanoides
• Stephania sutchuenensis
• Swertia japonica
• Tetraneuris acaulis
• Unonopsis glaucopetala
• Zieria smithii

Cross-Links

• PubChem: 101103171
• NPASS: NPC28811
• LOTUS: LTS0147460
• wikiData: Q104989366