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

Details

• Internal ID: c002add5-5baf-4dd6-9c6c-5e2300da6b3e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4R,5S,6R)-2-[(2S,3R,4R,5R,6S)-2-[[(2R,3R,5R,8R,9R,10S,12R,13R,14S,17S)-2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2R)-6-methyl-2-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CC(C(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)C)C)O)C)OC7C(C(C(C(O7)CO)O)O)O)C
• SMILES (Isomeric): CC(=CCC[C@](C)([C@H]1CC[C@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@]3(C[C@H]([C@@H](C4(C)C)O[C@@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O[C@H]6[C@@H]([C@@H]([C@@H]([C@H](O6)CO)O)O)O)O)C)C)O)C)O[C@H]7[C@H]([C@@H]([C@@H]([C@H](O7)CO)O)O)O)C
• InChI: InChI=1S/C48H82O19/c1-21(2)10-9-13-48(8,67-42-38(61)35(58)32(55)26(19-50)63-42)22-11-14-47(7)30(22)23(52)16-29-45(5)17-24(53)40(44(3,4)28(45)12-15-46(29,47)6)66-43-39(36(59)33(56)27(20-51)64-43)65-41-37(60)34(57)31(54)25(18-49)62-41/h10,22-43,49-61H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26+,27-,28-,29+,30-,31+,32+,33-,34+,35+,36+,37+,38-,39+,40-,41-,42-,43+,45+,46+,47-,48+/m0/s1
• InChI Key: VENRSYBHHVDBDC-GFHGIRBLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₂O₁₉
• Molecular Weight: 963.20 g/mol
• Exact Mass: 962.54503038 g/mol
• Topological Polar Surface Area (TPSA): 318.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): -1.06
• H-Bond Acceptor: 19
• H-Bond Donor: 13
• Rotatable Bonds: 13

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	-	0.9052	90.52%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8302	83.02%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7551	75.51%
P-glycoprotein inhibitior	+	0.7589	75.89%
P-glycoprotein substrate	-	0.6888	68.88%
CYP3A4 substrate	+	0.7153	71.53%
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	+	0.6372	63.72%
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	-	0.9040	90.40%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8313	83.13%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6806	68.06%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.5607	56.07%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7904	79.04%
Androgen receptor binding	+	0.7543	75.43%
Thyroid receptor binding	-	0.5207	52.07%
Glucocorticoid receptor binding	+	0.6998	69.98%
Aromatase binding	+	0.6520	65.20%
PPAR gamma	+	0.7830	78.30%
Honey bee toxicity	-	0.5298	52.98%
Biodegradation	-	0.7500	75.00%
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	98.85%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.81%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.80%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.53%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.27%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.49%	96.61%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.23%	97.36%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.84%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.46%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.43%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.04%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.00%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.11%	91.24%
CHEMBL226	P30542	Adenosine A1 receptor	87.86%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	85.85%	91.49%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.79%	97.14%
CHEMBL2996	Q05655	Protein kinase C delta	84.10%	97.79%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.72%	91.03%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.64%	95.83%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	81.65%	95.58%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.24%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	80.67%	95.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.60%	91.07%
CHEMBL2581	P07339	Cathepsin D	80.52%	98.95%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 125181830
• LOTUS: LTS0159268
• wikiData: Q105284729