(2S,3R,4S,5S,6R)-2-[(E,2R)-6-hydroperoxy-6-methyl-2-[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-2,3,12-trihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-4-en-2-yl]oxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol

Details

• Internal ID: 4946345c-2e8e-4a78-97c0-f8593601dee1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(E,2R)-6-hydroperoxy-6-methyl-2-[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-2,3,12-trihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-4-en-2-yl]oxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CC(C1O)O)C)CC(C4C3(CCC4C(C)(CC=CC(C)(C)OO)OC5C(C(C(C(O5)COC6C(C(C(CO6)O)O)O)O)O)O)C)O)C)C
• SMILES (Isomeric): C[C@@]12CC[C@@H]3[C@@]([C@H]1C[C@H]([C@H]4[C@]2(CC[C@@H]4[C@@](C)(C/C=C/C(C)(C)OO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)O)O)C)O)(C[C@H]([C@@H](C3(C)C)O)O)C
• InChI: InChI=1S/C41H70O15/c1-36(2,56-51)12-9-13-41(8,55-35-32(49)30(47)29(46)24(54-35)19-53-34-31(48)28(45)23(44)18-52-34)20-10-14-40(7)27(20)21(42)16-26-38(5)17-22(43)33(50)37(3,4)25(38)11-15-39(26,40)6/h9,12,20-35,42-51H,10-11,13-19H2,1-8H3/b12-9+/t20-,21+,22+,23+,24+,25-,26+,27-,28-,29+,30-,31+,32+,33-,34-,35-,38-,39+,40+,41+/m0/s1
• InChI Key: RSFZKHFMKIPRBP-MJOZEKTASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₇₀O₁₅
• Molecular Weight: 803.00 g/mol
• Exact Mass: 802.47147152 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.23
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6118	61.18%
Caco-2	-	0.8764	87.64%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6591	65.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8137	81.37%
OATP1B3 inhibitior	+	0.8945	89.45%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.4550	45.50%
P-glycoprotein inhibitior	+	0.7680	76.80%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7252	72.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8243	82.43%
CYP3A4 inhibition	-	0.9588	95.88%
CYP2C9 inhibition	-	0.8698	86.98%
CYP2C19 inhibition	-	0.8380	83.80%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	-	0.8780	87.80%
CYP2C8 inhibition	+	0.7076	70.76%
CYP inhibitory promiscuity	-	0.9472	94.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6274	62.74%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9090	90.90%
Skin irritation	-	0.6764	67.64%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.5371	53.71%
Human Ether-a-go-go-Related Gene inhibition	+	0.7189	71.89%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5718	57.18%
skin sensitisation	-	0.8798	87.98%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8089	80.89%
Acute Oral Toxicity (c)	I	0.4720	47.20%
Estrogen receptor binding	+	0.7212	72.12%
Androgen receptor binding	+	0.7230	72.30%
Thyroid receptor binding	-	0.5287	52.87%
Glucocorticoid receptor binding	+	0.6452	64.52%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.7234	72.34%
Honey bee toxicity	-	0.6360	63.60%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9459	94.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.08%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.03%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.85%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.78%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.24%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	93.69%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.44%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.54%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.46%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.07%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.38%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.53%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.68%	83.57%
CHEMBL1937	Q92769	Histone deacetylase 2	83.40%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.10%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.77%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.73%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	81.61%	95.38%
CHEMBL5028	O14672	ADAM10	81.10%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.03%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.47%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.37%	89.62%
CHEMBL1871	P10275	Androgen Receptor	80.21%	96.43%
CHEMBL2581	P07339	Cathepsin D	80.16%	98.95%

Plants that contains it

• Gymnema sylvestre

Cross-Links

• PubChem: 101619558
• LOTUS: LTS0178518
• wikiData: Q105244621