(2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aS,13R,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-13-methoxy-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: df01378c-c358-43b0-8494-051c3827e4af
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aS,13R,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-13-methoxy-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CC(C4C3(CCC5C4(CC(C(C5(C)CO)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)O)O)O)O)O)C)C)OC)C2C1)C)C(=O)O)C(=O)OC
• SMILES (Isomeric): C[C@@]1(CC[C@@]2(CC[C@@]3(C(=C[C@H]([C@H]4[C@]3(CC[C@@H]5[C@@]4(C[C@@H]([C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)C)C)OC)[C@@H]2C1)C)C(=O)O)C(=O)OC
• InChI: InChI=1S/C43H68O17/c1-38(37(54)56-7)10-12-43(36(52)53)13-11-41(4)20(21(43)15-38)14-23(55-6)32-39(2)16-22(46)33(40(3,19-45)26(39)8-9-42(32,41)5)60-34-30(50)28(48)25(18-57-34)59-35-31(51)29(49)27(47)24(17-44)58-35/h14,21-35,44-51H,8-13,15-19H2,1-7H3,(H,52,53)/t21-,22-,23+,24+,25+,26+,27+,28-,29-,30+,31+,32+,33-,34-,35-,38-,39-,40-,41+,42+,43-/m0/s1
• InChI Key: DSIITKWHWXIOEY-JRULUGAOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₈O₁₇
• Molecular Weight: 857.00 g/mol
• Exact Mass: 856.44565070 g/mol
• Topological Polar Surface Area (TPSA): 272.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.24
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8832	88.32%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8112	81.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7795	77.95%
OATP1B3 inhibitior	-	0.2293	22.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.7960	79.60%
P-glycoprotein inhibitior	+	0.7564	75.64%
P-glycoprotein substrate	+	0.6007	60.07%
CYP3A4 substrate	+	0.7322	73.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8833	88.33%
CYP2C9 inhibition	-	0.9285	92.85%
CYP2C19 inhibition	-	0.9205	92.05%
CYP2D6 inhibition	-	0.9538	95.38%
CYP1A2 inhibition	-	0.9078	90.78%
CYP2C8 inhibition	+	0.7292	72.92%
CYP inhibitory promiscuity	-	0.9806	98.06%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5987	59.87%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9089	90.89%
Skin irritation	-	0.5824	58.24%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7638	76.38%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7361	73.61%
skin sensitisation	-	0.9182	91.82%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5763	57.63%
Acute Oral Toxicity (c)	III	0.6557	65.57%
Estrogen receptor binding	+	0.7690	76.90%
Androgen receptor binding	+	0.7465	74.65%
Thyroid receptor binding	-	0.5751	57.51%
Glucocorticoid receptor binding	+	0.7040	70.40%
Aromatase binding	+	0.6543	65.43%
PPAR gamma	+	0.7794	77.94%
Honey bee toxicity	-	0.6909	69.09%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8974	89.74%

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	99.52%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	97.61%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.19%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.73%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.71%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.51%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.12%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.90%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.68%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.28%	99.23%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.95%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.86%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	83.85%	91.19%
CHEMBL4040	P28482	MAP kinase ERK2	83.54%	83.82%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.26%	91.07%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.26%	96.90%
CHEMBL5255	O00206	Toll-like receptor 4	83.05%	92.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.92%	97.33%
CHEMBL5028	O14672	ADAM10	82.87%	97.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.00%	95.83%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.43%	93.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.13%	94.00%

Plants that contains it

• Phytolacca americana

Cross-Links

• PubChem: 24770163
• LOTUS: LTS0188090
• wikiData: Q104987845