[(2S,3R,4S,5S)-5-hydroxy-3-[3-(4-hydroxyphenyl)propanoyloxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: 5d714511-e431-4210-8d0c-1e924e314094
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2S,3R,4S,5S)-5-hydroxy-3-[3-(4-hydroxyphenyl)propanoyloxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)O)C)C(=O)OC6C(C(C(CO6)O)OC7C(C(C(C(O7)CO)O)O)O)OC(=O)CCC8=CC=C(C=C8)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)OC(=O)CCC8=CC=C(C=C8)O)O)C)C)(C)C)O
• InChI: InChI=1S/C50H74O15/c1-45(2)20-21-50(29(22-45)28-13-14-33-47(5)18-17-34(54)46(3,4)32(47)16-19-48(33,6)49(28,7)23-35(50)55)44(60)65-43-41(63-36(56)15-10-26-8-11-27(52)12-9-26)40(30(53)25-61-43)64-42-39(59)38(58)37(57)31(24-51)62-42/h8-9,11-13,29-35,37-43,51-55,57-59H,10,14-25H2,1-7H3/t29-,30-,31+,32-,33+,34-,35+,37+,38-,39+,40-,41+,42-,43-,47-,48+,49+,50+/m0/s1
• InChI Key: CCLLWPLSBGBSKT-MIRIILCLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₄O₁₅
• Molecular Weight: 915.10 g/mol
• Exact Mass: 914.50277165 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8567	85.67%
Caco-2	-	0.8776	87.76%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8317	83.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7089	70.89%
OATP1B3 inhibitior	-	0.4152	41.52%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9045	90.45%
P-glycoprotein inhibitior	+	0.7543	75.43%
P-glycoprotein substrate	+	0.5933	59.33%
CYP3A4 substrate	+	0.7466	74.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8624	86.24%
CYP3A4 inhibition	-	0.7238	72.38%
CYP2C9 inhibition	-	0.8199	81.99%
CYP2C19 inhibition	-	0.8379	83.79%
CYP2D6 inhibition	-	0.9279	92.79%
CYP1A2 inhibition	-	0.7832	78.32%
CYP2C8 inhibition	+	0.8094	80.94%
CYP inhibitory promiscuity	-	0.9494	94.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5954	59.54%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9056	90.56%
Skin irritation	-	0.6597	65.97%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6759	67.59%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8902	89.02%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8998	89.98%
Acute Oral Toxicity (c)	III	0.6582	65.82%
Estrogen receptor binding	+	0.7993	79.93%
Androgen receptor binding	+	0.7508	75.08%
Thyroid receptor binding	+	0.5320	53.20%
Glucocorticoid receptor binding	+	0.7466	74.66%
Aromatase binding	+	0.5652	56.52%
PPAR gamma	+	0.8037	80.37%
Honey bee toxicity	-	0.6432	64.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5705	57.05%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.33%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.24%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.86%	95.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.06%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.61%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.93%	98.95%
CHEMBL233	P35372	Mu opioid receptor	90.69%	97.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.40%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.99%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	89.33%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.96%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.33%	94.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.21%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	87.47%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.71%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.57%	95.56%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.95%	89.05%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.68%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.68%	94.33%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.34%	92.67%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.95%	94.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.76%	96.77%
CHEMBL2514	O95665	Neurotensin receptor 2	81.93%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.90%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.86%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.82%	86.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.53%	96.61%

Plants that contains it

• Tragopogon porrifolius

Cross-Links

• PubChem: 162947514
• LOTUS: LTS0238382
• wikiData: Q104953447