(6S)-2-methyl-6-[(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]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-1-en-3-one

Details

• Internal ID: 0bef4a54-c005-4789-9717-b615200b0b33
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (6S)-2-methyl-6-[(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]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-1-en-3-one
• SMILES (Canonical): CC(=C)C(=O)CCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CC(C(C4(C)C)O)O)C)C)O)C)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O
• SMILES (Isomeric): CC(=C)C(=O)CC[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)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]([C@H](O6)CO)O)O)O)O)O)O
• InChI: InChI=1S/C42H70O15/c1-19(2)21(44)10-14-42(8,57-37-34(52)32(50)30(48)25(56-37)18-54-36-33(51)31(49)29(47)24(17-43)55-36)20-9-12-41(7)28(20)22(45)15-27-39(5)16-23(46)35(53)38(3,4)26(39)11-13-40(27,41)6/h20,22-37,43,45-53H,1,9-18H2,2-8H3/t20-,22+,23+,24+,25+,26-,27+,28-,29+,30+,31-,32-,33+,34+,35-,36+,37-,39-,40+,41+,42-/m0/s1
• InChI Key: VHAOZWPEPOPZFA-SDTZFMSQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₀O₁₅
• Molecular Weight: 815.00 g/mol
• Exact Mass: 814.47147152 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• BDBM50090474

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7532	75.32%
Caco-2	-	0.8910	89.10%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7797	77.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8125	81.25%
OATP1B3 inhibitior	-	0.2425	24.25%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.7276	72.76%
BSEP inhibitior	+	0.6555	65.55%
P-glycoprotein inhibitior	+	0.7528	75.28%
P-glycoprotein substrate	-	0.5922	59.22%
CYP3A4 substrate	+	0.7166	71.66%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.8723	87.23%
CYP3A4 inhibition	-	0.9192	91.92%
CYP2C9 inhibition	-	0.8356	83.56%
CYP2C19 inhibition	-	0.8825	88.25%
CYP2D6 inhibition	-	0.9389	93.89%
CYP1A2 inhibition	-	0.8922	89.22%
CYP2C8 inhibition	+	0.6630	66.30%
CYP inhibitory promiscuity	-	0.9530	95.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6708	67.08%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9090	90.90%
Skin irritation	-	0.5254	52.54%
Skin corrosion	-	0.9419	94.19%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7375	73.75%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5015	50.15%
skin sensitisation	-	0.8880	88.80%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.5616	56.16%
Acute Oral Toxicity (c)	III	0.4753	47.53%
Estrogen receptor binding	+	0.7653	76.53%
Androgen receptor binding	+	0.7479	74.79%
Thyroid receptor binding	-	0.5920	59.20%
Glucocorticoid receptor binding	+	0.6427	64.27%
Aromatase binding	+	0.6594	65.94%
PPAR gamma	+	0.7530	75.30%
Honey bee toxicity	-	0.6342	63.42%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9698	96.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	270 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.42%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.22%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.70%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.52%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.27%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.95%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.74%	100.00%
CHEMBL2581	P07339	Cathepsin D	89.14%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.71%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.77%	92.94%
CHEMBL220	P22303	Acetylcholinesterase	87.02%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.02%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.82%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.88%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.82%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	83.89%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.63%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.05%	91.24%
CHEMBL5028	O14672	ADAM10	81.33%	97.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.99%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.30%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.22%	97.36%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.05%	96.90%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 122179022
• LOTUS: LTS0245389
• wikiData: Q105286285