Asiaticoside

Details

• Internal ID: e160e4f4-b01f-4aca-b161-aeb644f20cf7
• 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)-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
• 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-FGWHUCSPSA-N
• Popularity: 35 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

• 16830-15-2
• Madecassol
• Asiaticosid
• Centelase
• Emdecassol
• PKO39VY215
• DTXSID30937476
• NSC-36002
• NSC-166062
• BA-2742
• RefChem:28503
• DTXCID201777735
• (2alpha,3beta)-2,3,23-Trihydroxyurs-12-en-28-oic acid, O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-O-beta-D-glucopyranosyl Ester
• 240-851-7
• ((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
• ((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)-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
• (6-((3,4-dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxymethyl)-3,4,5-trihydroxyoxan-2-yl) 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
• Dermatologico
• Blastoestimulina
• CHEBI:79928
• Asiaticoside (>90%)
• Ba 2742
• UNII-PKO39VY215
• CCRIS 8995
• MFCD06642601
• Madecassol (TN)
• Asiaticoside, 21
• EINECS 240-851-7
• NSC 36002
• NSC 166062
• BRN 0078195
• Asiaticoside (Standard)
• ASIATICOSIDE [MI]
• 4-17-00-03627 (Beilstein Handbook Reference)
• CENTELASE DERMATOLOGICO
• ASIATICOSIDE [USP-RS]
• ASIATICOSIDE [WHO-DD]
• orb1304613
• CHEMBL1684590
• SCHEMBL27500173
• BDBM23211
• HY-N0439R
• HMS6019B05
• HY-N0439
• MSK158086
• AKOS037514554
• DB14081
• (O-alpha-L-Rhamnopyranoxyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-O-beta-D-glucopyranosyl)-2alpha,3beta,23-trihydroxy-12-ursen-28-oat
• 2alpha,3beta,23-Trihydroxy-urs-12-en-28-saeure(O-alpha-L-rhamnopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-O-beta-D-glucopyranosyl)ester
• O-6-Desoxy-alpha-L-mannopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-O-beta-D-glucopyranosyl 2alpha,3beta,23-trihydroxy-12-ursen-28-at
• CS-0008960
• NS00018029
• D07576
• Q27149094
• ASIATICOSIDE (CONSTITUENT OF CENTELLA ASIATICA) [DSC]
• (2.ALPHA.,3.BETA.,4.ALPHA.)-2,3,23-TRIHYDROXYURS-12-EN-28-OIC ACID O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4)-O-.BETA.-D-GLUCOPYRANOSYL-(1->6)-O-.BETA.-D-GLUCOPYRANOSYL ESTER
• O-6-Deoxy-alpha-L-mannopyranosyl-(1.4)-O-beta-D-glucopyranosyl-(1.6)-beta-D-glucopyranosyl (2alpha,3beta,4alpha)-2,3,23-trihydroxyurs-12-en-28-oate
• URS-12-EN-28-OIC ACID, 2,3,23-TRIHYDROXY-, O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4)-O-.BETA.-D-GLUCOPYRANOSYL-(1->6)-.BETA.-D-GLUCOPYRANOSYL ESTER, (2.ALPHA.,3.BETA.,4.ALPHA.)-
• Urs-12-en-28-oic acid, 2,3,23-trihydroxy-, O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-beta-D-glucopyranosyl ester, (2alpha,3beta,4alpha)-
• Urs-12-en-28-oic acid, 2-alpha,3-beta,23-trihydroxy-, O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-o-beta-D-glucopyranosyl-(1-6)-o-beta-D-glucopyranosyl ester

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
• Akebia trifoliata
• Athanasia crithmifolia
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Centella asiatica
• Centella erecta
• Cerbera odollam
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Crateva magna
• Diospyros dendo
• Diospyros verrucosa
• Euonymus nanoides
• Heptapleurum heptaphyllum
• Jacobaea subalpina
• Narcissus tazetta
• Nepeta multifida
• Pleogyne australis
• Podophyllum grayi
• Polygala amara
• Primula veris
• Pyrola decorata
• Quercus serrata
• Rubus allegheniensis
• Salvia abrotanoides
• Solanum tuberosum
• Stephania sutchuenensis
• Swertia japonica
• Tetraneuris acaulis
• Unonopsis glaucopetala
• Zieria smithii

Cross-Links

• PubChem: 11954171
• NPASS: NPC172206
• LOTUS: LTS0212563
• wikiData: Q27149094