[(2S,3R,4S,5S)-5-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-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: 1c004016-7a55-4a89-bb8d-dc75ae60c020
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2S,3R,4S,5S)-5-hydroxy-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-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)C=CC8=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)/C=C/C8=CC=C(C=C8)O)O)C)C)(C)C)O
• InChI: InChI=1S/C50H72O15/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/h8-13,15,29-35,37-43,51-55,57-59H,14,16-25H2,1-7H3/b15-10+/t29-,30-,31+,32-,33+,34-,35+,37+,38-,39+,40-,41+,42-,43-,47-,48+,49+,50+/m0/s1
• InChI Key: MTYGCVPOKVNXNH-QQUXWNMZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₂O₁₅
• Molecular Weight: 913.10 g/mol
• Exact Mass: 912.48712159 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 3.90
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

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	-	0.8768	87.68%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8317	83.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7298	72.98%
OATP1B3 inhibitior	-	0.4152	41.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9327	93.27%
P-glycoprotein inhibitior	+	0.7521	75.21%
P-glycoprotein substrate	+	0.5279	52.79%
CYP3A4 substrate	+	0.7435	74.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8718	87.18%
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	+	0.8176	81.76%
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	-	0.9052	90.52%
Skin irritation	-	0.6597	65.97%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7477	74.77%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8902	89.02%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8815	88.15%
Acute Oral Toxicity (c)	III	0.6582	65.82%
Estrogen receptor binding	+	0.8005	80.05%
Androgen receptor binding	+	0.7496	74.96%
Thyroid receptor binding	+	0.5415	54.15%
Glucocorticoid receptor binding	+	0.7575	75.75%
Aromatase binding	+	0.5714	57.14%
PPAR gamma	+	0.8048	80.48%
Honey bee toxicity	-	0.6543	65.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5145	51.45%
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	99.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.29%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.73%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.88%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.46%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	92.94%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.26%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.17%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	91.99%	89.67%
CHEMBL226	P30542	Adenosine A1 receptor	90.77%	95.93%
CHEMBL206	P03372	Estrogen receptor alpha	89.45%	97.64%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.16%	100.00%
CHEMBL325	Q13547	Histone deacetylase 1	85.98%	95.92%
CHEMBL2581	P07339	Cathepsin D	83.96%	98.95%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.61%	89.44%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.61%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.77%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.05%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.02%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.70%	91.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.44%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.39%	93.99%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.26%	95.89%

Plants that contains it

• Tragopogon porrifolius

Cross-Links

• PubChem: 163193419
• LOTUS: LTS0006849
• wikiData: Q105171972