(3S,5S,8R,9S,10S,13R,14R,17S)-17-[(2S,3R,5S)-2-butoxy-3-hydroxy-5-(2-methylprop-1-enyl)oxolan-3-yl]-3-[(2S,3R,4S,5S)-5-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

Details

• Internal ID: 8b796916-7a71-4c07-ab6d-fc9e8cea5587
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,5S,8R,9S,10S,13R,14R,17S)-17-[(2S,3R,5S)-2-butoxy-3-hydroxy-5-(2-methylprop-1-enyl)oxolan-3-yl]-3-[(2S,3R,4S,5S)-5-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CCCCOC1C(CC(O1)C=C(C)C)(C2CCC3(C2CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(CO6)O)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)C)O)O)O)C=O)C)C)O
• SMILES (Isomeric): CCCCO[C@@H]1[C@@](C[C@H](O1)C=C(C)C)([C@H]2CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C=O)C)C)O
• InChI: InChI=1S/C50H82O17/c1-9-10-19-60-45-50(59,21-27(64-45)20-25(2)3)29-13-16-47(7)28(29)11-12-33-48(47,8)17-14-32-46(5,6)34(15-18-49(32,33)24-51)65-44-41(67-43-39(58)37(56)35(54)26(4)63-43)40(31(53)23-62-44)66-42-38(57)36(55)30(52)22-61-42/h20,24,26-45,52-59H,9-19,21-23H2,1-8H3/t26-,27+,28+,29-,30+,31-,32-,33-,34-,35-,36-,37+,38+,39+,40-,41+,42-,43-,44-,45-,47+,48+,49+,50+/m0/s1
• InChI Key: HUWGJMPWQLVCQI-FRELOJBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₂O₁₇
• Molecular Weight: 955.20 g/mol
• Exact Mass: 954.55520114 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9361	93.61%
Caco-2	-	0.8858	88.58%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8275	82.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8305	83.05%
OATP1B3 inhibitior	+	0.9152	91.52%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9489	94.89%
P-glycoprotein inhibitior	+	0.7542	75.42%
P-glycoprotein substrate	+	0.6975	69.75%
CYP3A4 substrate	+	0.7520	75.20%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8369	83.69%
CYP3A4 inhibition	-	0.8496	84.96%
CYP2C9 inhibition	-	0.8216	82.16%
CYP2C19 inhibition	-	0.8579	85.79%
CYP2D6 inhibition	-	0.9224	92.24%
CYP1A2 inhibition	-	0.9141	91.41%
CYP2C8 inhibition	+	0.8004	80.04%
CYP inhibitory promiscuity	-	0.8511	85.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5733	57.33%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9056	90.56%
Skin irritation	-	0.5448	54.48%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7581	75.81%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8943	89.43%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.4746	47.46%
Acute Oral Toxicity (c)	I	0.6098	60.98%
Estrogen receptor binding	+	0.8094	80.94%
Androgen receptor binding	+	0.7471	74.71%
Thyroid receptor binding	-	0.5248	52.48%
Glucocorticoid receptor binding	+	0.7137	71.37%
Aromatase binding	+	0.6592	65.92%
PPAR gamma	+	0.7909	79.09%
Honey bee toxicity	-	0.6403	64.03%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9851	98.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.57%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.15%	97.25%
CHEMBL2243	O00519	Anandamide amidohydrolase	95.97%	97.53%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.92%	91.11%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.17%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.25%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.16%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.72%	96.77%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	91.71%	92.86%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	91.30%	95.52%
CHEMBL255	P29275	Adenosine A2b receptor	89.93%	98.59%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.77%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.42%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.40%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	89.34%	95.93%
CHEMBL2581	P07339	Cathepsin D	89.13%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.02%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.88%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.86%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.64%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.42%	96.61%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.93%	89.05%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.71%	92.88%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.65%	95.89%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	85.15%	97.29%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.99%	97.14%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	83.98%	97.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.81%	92.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.61%	91.03%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.33%	95.71%
CHEMBL240	Q12809	HERG	83.25%	89.76%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.09%	94.33%
CHEMBL259	P32245	Melanocortin receptor 4	83.05%	95.38%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	83.04%	91.83%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.61%	97.36%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.57%	80.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.55%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.42%	95.56%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.13%	92.78%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.12%	95.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.95%	93.00%
CHEMBL4302	P08183	P-glycoprotein 1	81.73%	92.98%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.66%	100.00%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.65%	85.83%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.47%	80.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.41%	97.50%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.83%	86.67%
CHEMBL1951	P21397	Monoamine oxidase A	80.28%	91.49%
CHEMBL5255	O00206	Toll-like receptor 4	80.27%	92.50%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 162886301
• LOTUS: LTS0049791
• wikiData: Q105034082