Asiaticoside,(S)

Details

• Internal ID: aca9238f-74a2-4768-8aa3-506cb1e81ee2
• 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,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)O)O)C)C)C2C1C)C)C(=O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@H](O8)C)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C48H78O19/c1-20-10-13-48(15-14-46(6)23(29(48)21(20)2)8-9-28-44(4)16-24(51)39(60)45(5,19-50)27(44)11-12-47(28,46)7)43(61)67-42-36(58)33(55)31(53)26(65-42)18-62-40-37(59)34(56)38(25(17-49)64-40)66-41-35(57)32(54)30(52)22(3)63-41/h8,20-22,24-42,49-60H,9-19H2,1-7H3/t20-,21+,22-,24-,25-,26-,27-,28-,29+,30+,31-,32-,33+,34-,35-,36-,37-,38-,39+,40-,41+,42+,44+,45+,46-,47-,48+/m1/s1
• InChI Key: WYQVAPGDARQUBT-JVGKFWCXSA-N
• Popularity: 242 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): -1.03
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 9

Synonyms

• Asiaticoside,(S)
• D0P2IT
• CHEMBL1789965
• WYQVAPGDARQUBT-JVGKFWCXSA-N
• 16830-15-2
• Q63395738

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7336	73.36%
Caco-2	-	0.8904	89.04%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8246	82.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8899	88.99%
OATP1B3 inhibitior	-	0.4366	43.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.8614	86.14%
P-glycoprotein inhibitior	+	0.7420	74.20%
P-glycoprotein substrate	+	0.5178	51.78%
CYP3A4 substrate	+	0.7288	72.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9357	93.57%
CYP2C9 inhibition	-	0.9347	93.47%
CYP2C19 inhibition	-	0.9271	92.71%
CYP2D6 inhibition	-	0.9492	94.92%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.7354	73.54%
CYP inhibitory promiscuity	-	0.9709	97.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6290	62.90%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9070	90.70%
Skin irritation	-	0.5531	55.31%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7665	76.65%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9157	91.57%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.7721	77.21%
Acute Oral Toxicity (c)	III	0.6947	69.47%
Estrogen receptor binding	+	0.8513	85.13%
Androgen receptor binding	+	0.7573	75.73%
Thyroid receptor binding	-	0.4929	49.29%
Glucocorticoid receptor binding	+	0.7287	72.87%
Aromatase binding	+	0.6564	65.64%
PPAR gamma	+	0.8268	82.68%
Honey bee toxicity	-	0.6584	65.84%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5750	57.50%
Fish aquatic toxicity	+	0.9206	92.06%

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	99.23%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.32%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.05%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.74%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.02%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.05%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.49%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.51%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.71%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.56%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.00%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.42%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	84.29%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.10%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.56%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.86%	94.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.62%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	82.56%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.47%	96.77%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.46%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.83%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.78%	95.83%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.58%	94.33%

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: 52912190
• NPASS: NPC134835