Asiaticoside C

Details

• Internal ID: cb60c60a-038a-4ae2-b4ed-a8d939647a88
• 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] (1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-9-(acetyloxymethyl)-10,11-dihydroxy-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)COC(=O)C)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)COC(=O)C)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/C50H80O20/c1-21-11-14-50(16-15-48(7)25(31(50)22(21)2)9-10-30-46(5)17-26(53)41(62)47(6,20-65-24(4)52)29(46)12-13-49(30,48)8)45(63)70-44-38(60)35(57)33(55)28(68-44)19-64-42-39(61)36(58)40(27(18-51)67-42)69-43-37(59)34(56)32(54)23(3)66-43/h9,21-23,26-44,51,53-62H,10-20H2,1-8H3/t21-,22+,23+,26-,27-,28-,29-,30-,31+,32+,33-,34-,35+,36-,37-,38-,39-,40-,41+,42-,43+,44+,46+,47+,48-,49-,50+/m1/s1
• InChI Key: HUHPZZGDDVIBQX-QLRYCWKXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₀O₂₀
• Molecular Weight: 1001.20 g/mol
• Exact Mass: 1000.52429494 g/mol
• Topological Polar Surface Area (TPSA): 321.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.46
• H-Bond Acceptor: 20
• H-Bond Donor: 11
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6935	69.35%
Caco-2	-	0.8824	88.24%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8439	84.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8569	85.69%
OATP1B3 inhibitior	-	0.3315	33.15%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5298	52.98%
BSEP inhibitior	+	0.9511	95.11%
P-glycoprotein inhibitior	+	0.7481	74.81%
P-glycoprotein substrate	+	0.5602	56.02%
CYP3A4 substrate	+	0.7337	73.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8774	87.74%
CYP3A4 inhibition	-	0.8440	84.40%
CYP2C9 inhibition	-	0.9283	92.83%
CYP2C19 inhibition	-	0.9358	93.58%
CYP2D6 inhibition	-	0.9547	95.47%
CYP1A2 inhibition	-	0.9059	90.59%
CYP2C8 inhibition	+	0.7636	76.36%
CYP inhibitory promiscuity	-	0.9773	97.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6071	60.71%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9041	90.41%
Skin irritation	-	0.5279	52.79%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8108	81.08%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9251	92.51%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7377	73.77%
Acute Oral Toxicity (c)	III	0.7253	72.53%
Estrogen receptor binding	+	0.8370	83.70%
Androgen receptor binding	+	0.7572	75.72%
Thyroid receptor binding	+	0.5483	54.83%
Glucocorticoid receptor binding	+	0.7850	78.50%
Aromatase binding	+	0.6264	62.64%
PPAR gamma	+	0.8338	83.38%
Honey bee toxicity	-	0.6434	64.34%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5805	58.05%
Fish aquatic toxicity	+	0.9440	94.40%

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	99.41%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.56%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.79%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.45%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.12%	86.33%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	88.93%	91.65%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.68%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.42%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.30%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.87%	95.50%
CHEMBL2581	P07339	Cathepsin D	86.47%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.33%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.85%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	85.27%	94.73%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.83%	96.90%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.38%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	84.17%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.15%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.62%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	83.32%	95.93%
CHEMBL5028	O14672	ADAM10	83.01%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.93%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.93%	94.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.56%	81.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.51%	96.77%

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: 101103169
• NPASS: NPC166625
• LOTUS: LTS0224809
• wikiData: Q105033785