(3S,4S,5R,6S)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-[[(1S,2R,5R,7S,10R,11R,14R,15S,16S,17R,20R)-16-hydroxy-2,6,6,10,16-pentamethyl-17-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxane-3,4-diol

Details

• Internal ID: dba34ee3-1413-44b1-8f36-9afd3830cc46
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,4S,5R,6S)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-[[(1S,2R,5R,7S,10R,11R,14R,15S,16S,17R,20R)-16-hydroxy-2,6,6,10,16-pentamethyl-17-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxane-3,4-diol
• SMILES (Canonical): CC(=CC1COC23CC4(CO2)C(C3C1(C)O)CCC5C4(CCC6C5(CCC(C6(C)C)OC7C(C(C(CO7)O)O)OC8C(C(C(O8)CO)O)O)C)C)C
• SMILES (Isomeric): CC(=C[C@@H]1CO[C@]23C[C@]4(CO2)[C@@H]([C@H]3[C@@]1(C)O)CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@H]([C@@H](O8)CO)O)O)C)C)C
• InChI: InChI=1S/C40H64O12/c1-20(2)14-21-16-48-40-18-39(19-49-40)22(32(40)38(21,7)46)8-9-26-36(5)12-11-27(35(3,4)25(36)10-13-37(26,39)6)51-34-31(28(43)23(42)17-47-34)52-33-30(45)29(44)24(15-41)50-33/h14,21-34,41-46H,8-13,15-19H2,1-7H3/t21-,22-,23+,24+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,36+,37-,38+,39+,40-/m1/s1
• InChI Key: GHWPFBAAEVCXOY-XQEOOOGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₄O₁₂
• Molecular Weight: 736.90 g/mol
• Exact Mass: 736.43977747 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7395	73.95%
Caco-2	-	0.8741	87.41%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7487	74.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8231	82.31%
OATP1B3 inhibitior	+	0.8885	88.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.6954	69.54%
P-glycoprotein inhibitior	+	0.7671	76.71%
P-glycoprotein substrate	-	0.5425	54.25%
CYP3A4 substrate	+	0.7484	74.84%
CYP2C9 substrate	-	0.7915	79.15%
CYP2D6 substrate	-	0.8348	83.48%
CYP3A4 inhibition	-	0.9226	92.26%
CYP2C9 inhibition	-	0.8642	86.42%
CYP2C19 inhibition	-	0.9010	90.10%
CYP2D6 inhibition	-	0.9274	92.74%
CYP1A2 inhibition	-	0.9012	90.12%
CYP2C8 inhibition	+	0.6801	68.01%
CYP inhibitory promiscuity	-	0.9197	91.97%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5717	57.17%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9147	91.47%
Skin irritation	-	0.5769	57.69%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7725	77.25%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8994	89.94%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8499	84.99%
Acute Oral Toxicity (c)	I	0.6698	66.98%
Estrogen receptor binding	+	0.6545	65.45%
Androgen receptor binding	+	0.7498	74.98%
Thyroid receptor binding	-	0.5951	59.51%
Glucocorticoid receptor binding	+	0.6431	64.31%
Aromatase binding	+	0.6720	67.20%
PPAR gamma	+	0.7061	70.61%
Honey bee toxicity	-	0.5705	57.05%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9306	93.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL325	Q13547	Histone deacetylase 1	97.12%	95.92%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.98%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.84%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	93.86%	95.93%
CHEMBL1937	Q92769	Histone deacetylase 2	91.84%	94.75%
CHEMBL2581	P07339	Cathepsin D	90.27%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.04%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.65%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.74%	97.28%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.70%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.67%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.72%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.60%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.83%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.72%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.62%	91.24%
CHEMBL3589	P55263	Adenosine kinase	84.46%	98.05%
CHEMBL3524	P56524	Histone deacetylase 4	83.24%	92.97%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	83.21%	97.86%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.01%	95.58%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.50%	98.75%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.87%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.64%	92.62%
CHEMBL5028	O14672	ADAM10	80.22%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	80.08%	90.17%

Plants that contains it

• Bacopa monnieri

Cross-Links

• PubChem: 154496229
• LOTUS: LTS0103107
• wikiData: Q105008786