(3S,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-3,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(methoxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicene-4-carboxylic acid

Details

• Internal ID: 61219575-f332-4365-ab72-ea054c9d2e7a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (3S,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-3,12-dihydroxy-4,6a,6b,11,12,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(methoxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicene-4-carboxylic acid
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C(=O)O)O)C)C)C2C1(C)O)C)C(=O)OC6C(C(C(C(O6)COC)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)C(=O)O)O)C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COC)O)O)O
• InChI: InChI=1S/C37H58O11/c1-19-10-15-37(31(44)48-29-27(41)26(40)25(39)21(47-29)18-46-7)17-16-33(3)20(28(37)36(19,6)45)8-9-22-32(2)13-12-24(38)35(5,30(42)43)23(32)11-14-34(22,33)4/h8,19,21-29,38-41,45H,9-18H2,1-7H3,(H,42,43)/t19-,21-,22-,23-,24+,25-,26+,27-,28-,29+,32-,33-,34-,35-,36-,37+/m1/s1
• InChI Key: GEGMKDORGBDYDI-NVGRWCCCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₈O₁₁
• Molecular Weight: 678.80 g/mol
• Exact Mass: 678.39791266 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8667	86.67%
Caco-2	-	0.8449	84.49%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8250	82.50%
OATP2B1 inhibitior	-	0.7296	72.96%
OATP1B1 inhibitior	+	0.8477	84.77%
OATP1B3 inhibitior	+	0.8795	87.95%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6564	65.64%
BSEP inhibitior	-	0.4520	45.20%
P-glycoprotein inhibitior	+	0.7476	74.76%
P-glycoprotein substrate	-	0.5846	58.46%
CYP3A4 substrate	+	0.7169	71.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8751	87.51%
CYP3A4 inhibition	-	0.8042	80.42%
CYP2C9 inhibition	-	0.8966	89.66%
CYP2C19 inhibition	-	0.8942	89.42%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.8516	85.16%
CYP2C8 inhibition	+	0.6398	63.98%
CYP inhibitory promiscuity	-	0.9787	97.87%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6837	68.37%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.5589	55.89%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.7970	79.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4678	46.78%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8951	89.51%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.9221	92.21%
Acute Oral Toxicity (c)	III	0.5186	51.86%
Estrogen receptor binding	+	0.6519	65.19%
Androgen receptor binding	+	0.7292	72.92%
Thyroid receptor binding	-	0.5711	57.11%
Glucocorticoid receptor binding	+	0.7208	72.08%
Aromatase binding	+	0.6624	66.24%
PPAR gamma	+	0.6744	67.44%
Honey bee toxicity	-	0.7992	79.92%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9441	94.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.00%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.95%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.79%	97.36%
CHEMBL2581	P07339	Cathepsin D	91.16%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.55%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.06%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.81%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	88.21%	92.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.69%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.41%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.86%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.43%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.27%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.70%	93.00%
CHEMBL5028	O14672	ADAM10	81.65%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.59%	97.25%

Plants that contains it

• Rubus pileatus

Cross-Links

• PubChem: 102276787
• LOTUS: LTS0269069
• wikiData: Q105007152