(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4-methoxycarbonyl-4,6a,6b,11,11,14b-hexamethyl-10-(2-methylbut-2-enoyloxy)-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: 2495c842-28fc-4b7c-b54c-f0938f61fa4c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4-methoxycarbonyl-4,6a,6b,11,11,14b-hexamethyl-10-(2-methylbut-2-enoyloxy)-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C(=O)OC)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)O)O)C)CO)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@@]5(C)C(=O)OC)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O)C)C)C)O)CO)(C)C)OC(=O)C(=CC)C
• InChI: InChI=1S/C52H78O19/c1-12-24(3)42(62)70-39-40(71-43(63)25(4)13-2)52(23-53)27(20-47(39,5)6)26-14-15-29-48(7)18-17-32(51(10,46(64)65-11)30(48)16-19-49(29,8)50(26,9)21-31(52)55)67-45-36(59)37(35(58)38(69-45)41(60)61)68-44-34(57)33(56)28(54)22-66-44/h12-14,27-40,44-45,53-59H,15-23H2,1-11H3,(H,60,61)/b24-12?,25-13-/t27-,28-,29+,30+,31+,32-,33-,34+,35-,36+,37-,38-,39-,40-,44-,45+,48+,49+,50+,51-,52-/m0/s1
• InChI Key: KUGYOOSOCMQUAK-BDLIFLARSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₇₈O₁₉
• Molecular Weight: 1007.20 g/mol
• Exact Mass: 1006.51373025 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7524	75.24%
Caco-2	-	0.8658	86.58%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8446	84.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7990	79.90%
OATP1B3 inhibitior	-	0.3173	31.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9321	93.21%
P-glycoprotein inhibitior	+	0.7517	75.17%
P-glycoprotein substrate	+	0.5703	57.03%
CYP3A4 substrate	+	0.7397	73.97%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8966	89.66%
CYP3A4 inhibition	-	0.8504	85.04%
CYP2C9 inhibition	-	0.8702	87.02%
CYP2C19 inhibition	-	0.9017	90.17%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9011	90.11%
CYP2C8 inhibition	+	0.7779	77.79%
CYP inhibitory promiscuity	-	0.9771	97.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5934	59.34%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9003	90.03%
Skin irritation	-	0.6306	63.06%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.6748	67.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.6918	69.18%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7069	70.69%
skin sensitisation	-	0.8954	89.54%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.5577	55.77%
Acute Oral Toxicity (c)	III	0.7499	74.99%
Estrogen receptor binding	+	0.7422	74.22%
Androgen receptor binding	+	0.7552	75.52%
Thyroid receptor binding	+	0.6036	60.36%
Glucocorticoid receptor binding	+	0.8020	80.20%
Aromatase binding	+	0.6289	62.89%
PPAR gamma	+	0.8286	82.86%
Honey bee toxicity	-	0.6622	66.22%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9235	92.35%

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	99.08%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.01%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.44%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.97%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.72%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.50%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.84%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.50%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.37%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.26%	98.95%
CHEMBL5028	O14672	ADAM10	85.13%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.12%	99.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.05%	89.67%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.46%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.40%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.22%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.21%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.81%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.64%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.63%	96.90%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.13%	89.00%

Plants that contains it

• Polyspora chrysandra

Cross-Links

• PubChem: 163043697
• LOTUS: LTS0125110
• wikiData: Q105146141