[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR)-10-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,13-dodecahydro-2H-picene-4a-carboxylate

Details

• Internal ID: 058290d3-5cdb-4cc0-936e-019c66442591
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR)-10-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,10,11,12,13-dodecahydro-2H-picene-4a-carboxylate
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)O)C)C)C2=C1C)C)C(=O)OC6C(C(C(C(O6)CO)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(CC[C@@H]([C@@]5(C)CO)O)C)C)C2=C1C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C36H56O9/c1-19-9-14-36(31(43)45-30-29(42)28(41)27(40)22(17-37)44-30)16-15-34(5)21(26(36)20(19)2)7-8-24-32(3)12-11-25(39)33(4,18-38)23(32)10-13-35(24,34)6/h7,19,22-25,27-30,37-42H,8-18H2,1-6H3/t19-,22-,23-,24-,25+,27-,28+,29-,30+,32+,33+,34-,35-,36+/m1/s1
• InChI Key: ZMOGQUZDNDWVKU-KSYMCXMQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₆O₉
• Molecular Weight: 632.80 g/mol
• Exact Mass: 632.39243336 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.38
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 3beta,23-Dihydroxyurs-12,18-diene-28-oic acid beta-D-glucopyranosyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7816	78.16%
Caco-2	-	0.8228	82.28%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8204	82.04%
OATP2B1 inhibitior	-	0.5788	57.88%
OATP1B1 inhibitior	+	0.8694	86.94%
OATP1B3 inhibitior	-	0.3793	37.93%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.6601	66.01%
P-glycoprotein inhibitior	+	0.6860	68.60%
P-glycoprotein substrate	-	0.6411	64.11%
CYP3A4 substrate	+	0.7226	72.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8541	85.41%
CYP3A4 inhibition	-	0.8962	89.62%
CYP2C9 inhibition	-	0.9176	91.76%
CYP2C19 inhibition	-	0.8899	88.99%
CYP2D6 inhibition	-	0.9428	94.28%
CYP1A2 inhibition	-	0.8393	83.93%
CYP2C8 inhibition	+	0.6580	65.80%
CYP inhibitory promiscuity	-	0.9592	95.92%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6960	69.60%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9224	92.24%
Skin irritation	-	0.5684	56.84%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	-	0.7807	78.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.7210	72.10%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9134	91.34%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8002	80.02%
Acute Oral Toxicity (c)	III	0.7112	71.12%
Estrogen receptor binding	+	0.6521	65.21%
Androgen receptor binding	+	0.7461	74.61%
Thyroid receptor binding	-	0.5452	54.52%
Glucocorticoid receptor binding	+	0.7072	70.72%
Aromatase binding	+	0.6630	66.30%
PPAR gamma	+	0.6329	63.29%
Honey bee toxicity	-	0.7409	74.09%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5382	53.82%
Fish aquatic toxicity	+	0.9323	93.23%

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	95.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.27%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.95%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.87%	100.00%
CHEMBL2581	P07339	Cathepsin D	85.07%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.51%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.31%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.75%	94.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.68%	89.05%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.35%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.33%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.99%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.94%	95.89%
CHEMBL5028	O14672	ADAM10	80.78%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.27%	95.89%

Plants that contains it

• Ilex oblonga
• Taraxacum officinale
• Terminalia chebula

Cross-Links

• PubChem: 76308704
• NPASS: NPC190837
• LOTUS: LTS0251476
• wikiData: Q105379596