(2S,4aS,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bR)-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)-2-methoxycarbonyl-4a,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylic acid

Details

• Internal ID: 73a758a4-ee68-49a4-8e46-0434dd0ccf63
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,4aS,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bR)-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)-2-methoxycarbonyl-4a,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylic acid
• SMILES (Canonical): CC12CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)O)O)O)O)O)C)C)C1CC(CC2)(C(=O)O)C(=O)OC)C
• SMILES (Isomeric): C[C@@]12CC[C@@]3(C(=CC[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)[C@@H]1C[C@@](CC2)(C(=O)O)C(=O)OC)C
• InChI: InChI=1S/C42H66O16/c1-37-11-13-40(4)20(21(37)15-42(14-12-37,35(51)52)36(53)54-6)7-8-26-38(2)16-22(45)32(39(3,19-44)25(38)9-10-41(26,40)5)58-33-30(49)28(47)24(18-55-33)57-34-31(50)29(48)27(46)23(17-43)56-34/h7,21-34,43-50H,8-19H2,1-6H3,(H,51,52)/t21-,22-,23+,24+,25+,26+,27+,28-,29-,30+,31+,32-,33-,34-,37-,38-,39-,40+,41+,42-/m0/s1
• InChI Key: LCWHVPVEMRQLCE-OWRBLJEPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₁₆
• Molecular Weight: 827.00 g/mol
• Exact Mass: 826.43508601 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• AC-34725
• Q-100745

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8816	88.16%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8112	81.12%
OATP2B1 inhibitior	-	0.8791	87.91%
OATP1B1 inhibitior	+	0.8257	82.57%
OATP1B3 inhibitior	-	0.2293	22.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.6712	67.12%
P-glycoprotein inhibitior	+	0.7553	75.53%
P-glycoprotein substrate	+	0.5176	51.76%
CYP3A4 substrate	+	0.7283	72.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8825	88.25%
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	+	0.7243	72.43%
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	-	0.9100	91.00%
Skin irritation	-	0.5824	58.24%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7126	71.26%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.8102	81.02%
skin sensitisation	-	0.9182	91.82%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5386	53.86%
Acute Oral Toxicity (c)	III	0.6557	65.57%
Estrogen receptor binding	+	0.7475	74.75%
Androgen receptor binding	+	0.7451	74.51%
Thyroid receptor binding	-	0.6255	62.55%
Glucocorticoid receptor binding	+	0.6597	65.97%
Aromatase binding	+	0.6528	65.28%
PPAR gamma	+	0.7590	75.90%
Honey bee toxicity	-	0.7206	72.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
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	99.32%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.16%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	95.81%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.22%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.00%	97.36%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.06%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.75%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.39%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.93%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.92%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.48%	95.89%
CHEMBL5028	O14672	ADAM10	84.61%	97.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.13%	91.24%
CHEMBL2581	P07339	Cathepsin D	83.86%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.50%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.21%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.35%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.15%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.09%	95.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.60%	96.90%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.73%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.42%	99.23%

Plants that contains it

• Phytolacca acinosa
• Phytolacca americana

Cross-Links

• PubChem: 24721282
• NPASS: NPC131733