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

Details

• Internal ID: 207b4563-d4f7-473f-9f7f-f08d14d85b14
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(E,2S)-6-hydroperoxy-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-4-en-2-yl]-2,12-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CC(C1OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)O)C)CC(C6C3(CCC6C(C)(CC=CC(C)(C)OO)OC7C(C(C(C(O7)CO)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)O)O)O)C)O)(C[C@H]([C@@H](C3(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)C
• InChI: InChI=1S/C48H82O21/c1-43(2,69-62)12-9-13-48(8,68-41-37(61)34(58)31(55)25(19-50)64-41)21-10-14-47(7)29(21)22(52)16-28-45(5)17-23(53)39(44(3,4)27(45)11-15-46(28,47)6)67-42-38(35(59)32(56)26(20-51)65-42)66-40-36(60)33(57)30(54)24(18-49)63-40/h9,12,21-42,49-62H,10-11,13-20H2,1-8H3/b12-9+/t21-,22+,23+,24+,25+,26+,27-,28+,29-,30+,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42-,45-,46+,47+,48-/m0/s1
• InChI Key: JWUIALRFPUOOAH-SIDAWKLTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₂O₂₁
• Molecular Weight: 995.20 g/mol
• Exact Mass: 994.53485962 g/mol
• Topological Polar Surface Area (TPSA): 348.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.59
• H-Bond Acceptor: 21
• H-Bond Donor: 14
• Rotatable Bonds: 14

Synonyms

• BDBM50090478

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5627	56.27%
Caco-2	-	0.8931	89.31%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6365	63.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8183	81.83%
OATP1B3 inhibitior	+	0.8884	88.84%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7792	77.92%
P-glycoprotein inhibitior	+	0.7514	75.14%
P-glycoprotein substrate	-	0.5867	58.67%
CYP3A4 substrate	+	0.7252	72.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8308	83.08%
CYP3A4 inhibition	-	0.9413	94.13%
CYP2C9 inhibition	-	0.8698	86.98%
CYP2C19 inhibition	-	0.8543	85.43%
CYP2D6 inhibition	-	0.9414	94.14%
CYP1A2 inhibition	-	0.8765	87.65%
CYP2C8 inhibition	+	0.6616	66.16%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6368	63.68%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9030	90.30%
Skin irritation	-	0.6823	68.23%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8081	80.81%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5329	53.29%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.5821	58.21%
Acute Oral Toxicity (c)	I	0.4658	46.58%
Estrogen receptor binding	+	0.7708	77.08%
Androgen receptor binding	+	0.7512	75.12%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7414	74.14%
Aromatase binding	+	0.6449	64.49%
PPAR gamma	+	0.7871	78.71%
Honey bee toxicity	-	0.5650	56.50%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9060	90.60%

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	98.88%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.56%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.23%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.15%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.64%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.20%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.00%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.63%	92.94%
CHEMBL226	P30542	Adenosine A1 receptor	90.62%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.16%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.46%	91.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.00%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.40%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.17%	82.69%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	85.80%	91.83%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.79%	95.58%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.49%	91.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.68%	91.07%
CHEMBL259	P32245	Melanocortin receptor 4	83.49%	95.38%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.45%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.94%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.55%	95.83%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.19%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.04%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.19%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.00%	96.21%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 122179018
• LOTUS: LTS0260977
• wikiData: Q105136371