(2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-[[(1S,2R,5R,7S,10S,11R,12S,15S,20S,21S,23R)-12-hydroxy-20-(hydroxymethyl)-1,2,6,6,10,17,17-heptamethyl-22-oxahexacyclo[12.9.0.02,11.05,10.015,20.021,23]tricos-13-en-7-yl]oxy]-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol

Details

• Internal ID: 46be217d-efc9-4809-ba40-98eb856f50ae
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-[[(1S,2R,5R,7S,10S,11R,12S,15S,20S,21S,23R)-12-hydroxy-20-(hydroxymethyl)-1,2,6,6,10,17,17-heptamethyl-22-oxahexacyclo[12.9.0.02,11.05,10.015,20.021,23]tricos-13-en-7-yl]oxy]-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2(C)C)CCC4(C3C(C=C5C4(C6C(O6)C7(C5CC(CC7)(C)C)CO)C)O)C)C)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(CO9)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]4([C@@H]3[C@H](C=C5[C@]4([C@@H]6[C@@H](O6)[C@@]7([C@H]5CC(CC7)(C)C)CO)C)O)C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O)O
• InChI: InChI=1S/C47H76O17/c1-20-28(52)31(55)34(63-41-35(32(56)30(54)25(17-48)60-41)62-39-33(57)29(53)24(51)18-58-39)40(59-20)61-27-10-11-44(6)26(43(27,4)5)9-12-45(7)36(44)23(50)15-21-22-16-42(2,3)13-14-47(22,19-49)38-37(64-38)46(21,45)8/h15,20,22-41,48-57H,9-14,16-19H2,1-8H3/t20-,22+,23+,24-,25-,26+,27+,28+,29+,30-,31+,32+,33-,34-,35-,36-,37+,38-,39+,40+,41+,44+,45-,46+,47-/m1/s1
• InChI Key: WWPPXDAMFHMHKT-GOPUORMMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₇
• Molecular Weight: 913.10 g/mol
• Exact Mass: 912.50825095 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.24
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7235	72.35%
Caco-2	-	0.8964	89.64%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7257	72.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7649	76.49%
OATP1B3 inhibitior	-	0.2332	23.32%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.4590	45.90%
P-glycoprotein inhibitior	+	0.7508	75.08%
P-glycoprotein substrate	-	0.5374	53.74%
CYP3A4 substrate	+	0.7377	73.77%
CYP2C9 substrate	-	0.8034	80.34%
CYP2D6 substrate	-	0.8362	83.62%
CYP3A4 inhibition	-	0.9376	93.76%
CYP2C9 inhibition	-	0.7641	76.41%
CYP2C19 inhibition	-	0.8402	84.02%
CYP2D6 inhibition	-	0.9273	92.73%
CYP1A2 inhibition	-	0.8466	84.66%
CYP2C8 inhibition	+	0.6729	67.29%
CYP inhibitory promiscuity	-	0.9600	96.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6439	64.39%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9064	90.64%
Skin irritation	-	0.6692	66.92%
Skin corrosion	-	0.9389	93.89%
Ames mutagenesis	-	0.6437	64.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7446	74.46%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.7031	70.31%
skin sensitisation	-	0.8572	85.72%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.9313	93.13%
Acute Oral Toxicity (c)	III	0.6120	61.20%
Estrogen receptor binding	+	0.7900	79.00%
Androgen receptor binding	+	0.7300	73.00%
Thyroid receptor binding	-	0.5684	56.84%
Glucocorticoid receptor binding	+	0.6579	65.79%
Aromatase binding	+	0.6448	64.48%
PPAR gamma	+	0.7710	77.10%
Honey bee toxicity	-	0.6387	63.87%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9278	92.78%

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	99.33%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.95%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.36%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.48%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	89.92%	94.75%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.48%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.20%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.15%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.87%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.48%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.43%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.36%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.02%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.55%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.09%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.03%	96.61%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.25%	97.53%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.19%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.50%	95.56%
CHEMBL3589	P55263	Adenosine kinase	81.38%	98.05%
CHEMBL5028	O14672	ADAM10	80.35%	97.50%

Plants that contains it

• Bupleurum rotundifolium

Cross-Links

• PubChem: 163039815
• LOTUS: LTS0256744
• wikiData: Q105314205