(2S,3R,4S,5S,6R)-2-[(E)-2-(3,12-dihydroxy-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)-7-hydroxy-6-methylhept-5-en-2-yl]oxy-6-[[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol

Details

• Internal ID: 82c4b6cd-ece8-4412-a425-6b4667f58112
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(E)-2-(3,12-dihydroxy-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)-7-hydroxy-6-methylhept-5-en-2-yl]oxy-6-[[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)O)C)C)O)C)OC5C(C(C(C(O5)COC6C(C(C(CO6)O)O)O)O)O)O)CO
• SMILES (Isomeric): C/C(=C\CCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)O)C)C)O)C)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)/CO
• InChI: InChI=1S/C41H70O13/c1-21(18-42)9-8-13-41(7,54-36-34(50)32(48)31(47)25(53-36)20-52-35-33(49)30(46)24(44)19-51-35)22-10-15-40(6)29(22)23(43)17-27-38(4)14-12-28(45)37(2,3)26(38)11-16-39(27,40)5/h9,22-36,42-50H,8,10-20H2,1-7H3/b21-9+/t22?,23?,24-,25-,26?,27?,28?,29?,30+,31-,32+,33-,34-,35-,36+,38?,39?,40?,41?/m1/s1
• InChI Key: IXEOEFBIJPVHES-RXBMYJGVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₇₀O₁₃
• Molecular Weight: 771.00 g/mol
• Exact Mass: 770.48164228 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8851	88.51%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	0.8695	86.95%
OATP1B1 inhibitior	+	0.8477	84.77%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.4740	47.40%
P-glycoprotein inhibitior	+	0.7732	77.32%
P-glycoprotein substrate	-	0.5752	57.52%
CYP3A4 substrate	+	0.7323	73.23%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.6776	67.76%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9138	91.38%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.5895	58.95%
Human Ether-a-go-go-Related Gene inhibition	+	0.8064	80.64%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6264	62.64%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8590	85.90%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7255	72.55%
Androgen receptor binding	+	0.7278	72.78%
Thyroid receptor binding	-	0.5863	58.63%
Glucocorticoid receptor binding	+	0.6270	62.70%
Aromatase binding	+	0.6952	69.52%
PPAR gamma	+	0.7253	72.53%
Honey bee toxicity	-	0.5975	59.75%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9172	91.72%

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	97.76%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.07%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.02%	95.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.38%	82.69%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.31%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.71%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.59%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.13%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.87%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.67%	96.77%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.25%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.70%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.54%	97.36%
CHEMBL2179	P04062	Beta-glucocerebrosidase	85.28%	85.31%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.48%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.41%	89.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.12%	96.90%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.23%	80.33%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.71%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.30%	92.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.23%	92.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.17%	95.83%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	80.93%	92.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.71%	94.75%
CHEMBL2996	Q05655	Protein kinase C delta	80.42%	97.79%
CHEMBL259	P32245	Melanocortin receptor 4	80.30%	95.38%
CHEMBL1871	P10275	Androgen Receptor	80.28%	96.43%
CHEMBL5957	P21589	5'-nucleotidase	80.08%	97.78%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.05%	97.14%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 11968570
• NPASS: NPC220164
• LOTUS: LTS0214653
• wikiData: Q105122100