Madecassoside

Details

• Internal ID: 41be421a-45bf-4e91-9bb2-c83caf015870
• 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,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-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(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)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(C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)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/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3/t19-,20+,21+,23-,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: BNMGUJRJUUDLHW-HCZMHFOYSA-N
• Popularity: 79 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₂₀
• Molecular Weight: 975.10 g/mol
• Exact Mass: 974.50864487 g/mol
• Topological Polar Surface Area (TPSA): 335.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.06
• H-Bond Acceptor: 20
• H-Bond Donor: 13
• Rotatable Bonds: 9

Synonyms

• Redermic
• ASIATICOSIDE A
• UNII-CQ2F5O6YIY
• CQ2F5O6YIY
• 34540-22-2
• EINECS 252-076-1
• CHEBI:66651
• O-6-Deoxy-alpha-L-mannopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl(2alpha,3beta,4alpha,6beta)-2,3,6,23-tetrahydroxyurs-12-en-28-oate
• 6-deoxy-alpha-L-mannopyranosyl-(1->4)-beta-D-glucopyranosyl-(1->6)-1-O-[(2alpha,3beta,6beta)-2,3,6,23-tetrahydroxy-28-oxours-12-en-28-yl]-beta-D-glucopyranose
• O-6-Deoxy-alpha-L-mannopyranosyl-(1.4)-O-beta-D-glucopyranosyl-(1.6)-beta-D-glucopyranosyl (2alpha,3beta,4alpha,6beta)-2,3,6,23-tetrahydroxyurs-12-en-28-oate
• C48H78O20
• C48-H78-O20
• 6-deoxy-alpha-L-mannopyranosyl-(1->4)-beta-D-glucopyranosyl-(1->6)-1-O-((2alpha,3beta,6beta)-2,3,6,23-tetrahydroxy-28-oxours-12-en-28-yl)-beta-D-glucopyranose
• Ursane Triterpene, 22
• MADECASSOSIDE [INCI]
• MADECASSOSIDE [WHO-DD]
• CHEMBL4787233
• BDBM23212
• DTXSID40956057
• O-6-deoxy-alpha-L-mannopyranosyl-(1.fwdarw.4)-O-beta-D-glucopyranosyl-(1.fwdarw.6)-beta-D-glucopyranosyl (2alpha,3beta,4alpha,6beta)-2,3,6,23-tetrahydroxyurs-12-en-28-oate
• AKOS037514732
• DB15532
• MADECASSOSIDE (CONSTITUENT OF CENTELLA ASIATICA)
• MADECASSOSIDE (CONSTITUENT OF CENTELLA ASIATICA) [DSC]
• [(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,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-t
• Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, O-6-deoxy-alpha-L-mannopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, (2alpha,3beta,4alpha,6beta)-
• Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, O-6-deoxy-alpha-L-mannopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl ester, (2alpha,3beta,4alpha,6beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7336	73.36%
Caco-2	-	0.8883	88.83%
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	+	0.8896	88.96%
OATP1B3 inhibitior	-	0.4366	43.66%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.8438	84.38%
P-glycoprotein inhibitior	+	0.7409	74.09%
P-glycoprotein substrate	+	0.5617	56.17%
CYP3A4 substrate	+	0.7293	72.93%
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	+	0.7448	74.48%
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	-	0.9056	90.56%
Skin irritation	-	0.5531	55.31%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7446	74.46%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9157	91.57%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.8310	83.10%
Acute Oral Toxicity (c)	III	0.6947	69.47%
Estrogen receptor binding	+	0.8493	84.93%
Androgen receptor binding	+	0.7549	75.49%
Thyroid receptor binding	+	0.5139	51.39%
Glucocorticoid receptor binding	+	0.7280	72.80%
Aromatase binding	+	0.6528	65.28%
PPAR gamma	+	0.8232	82.32%
Honey bee toxicity	-	0.6494	64.94%
Biodegradation	-	0.7250	72.50%
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	99.42%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.21%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.65%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.61%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.44%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.25%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.56%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.45%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.00%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.55%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.49%	86.92%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.96%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.65%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	85.33%	92.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.12%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.64%	96.77%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.60%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.66%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.52%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.24%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.02%	95.89%

Plants that contains it

• Achillea clypeolata
• Actaea asiatica
• Actaea cimicifuga
• Actaea dahurica
• Actaea simplex
• Athanasia crithmifolia
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Centella asiatica
• Centella erecta
• 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: 24825675
• NPASS: NPC114470
• LOTUS: LTS0276487
• wikiData: Q104938890