(2R,3R,4S,5S,6R)-2-[[(2S,3S,5R)-5-[(1S)-1-[(3R,5R,9R,10S,13S,14R,16S,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-ethyl-2-methyloxolan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: b4f40d62-0de8-4435-8450-038bd96c58c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2S,3S,5R)-5-[(1S)-1-[(3R,5R,9R,10S,13S,14R,16S,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-3-ethyl-2-methyloxolan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CCC1CC(OC1(C)COC2C(C(C(C(O2)CO)O)O)O)C(C)C3C(CC4C3(CCC5C4=CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)O
• SMILES (Isomeric): CC[C@H]1C[C@@H](O[C@]1(C)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@@]3(CC[C@H]5C4=CC[C@H]6[C@@]5(CC[C@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)O
• InChI: InChI=1S/C47H78O19/c1-6-21-14-28(66-47(21,5)19-60-42-39(58)36(55)33(52)29(16-48)62-42)20(2)32-27(51)15-26-24-8-7-22-13-23(9-11-45(22,3)25(24)10-12-46(26,32)4)61-44-41(38(57)35(54)31(18-50)64-44)65-43-40(59)37(56)34(53)30(17-49)63-43/h8,20-23,25-44,48-59H,6-7,9-19H2,1-5H3/t20-,21+,22-,23-,25+,26+,27+,28-,29-,30-,31-,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42-,43+,44-,45+,46+,47-/m1/s1
• InChI Key: VBNAXQCYAJUWPW-XPSSGPODSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₈O₁₉
• Molecular Weight: 947.10 g/mol
• Exact Mass: 946.51373025 g/mol
• Topological Polar Surface Area (TPSA): 307.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8476	84.76%
Caco-2	-	0.8859	88.59%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6786	67.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8589	85.89%
OATP1B3 inhibitior	+	0.9092	90.92%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6890	68.90%
P-glycoprotein inhibitior	+	0.7387	73.87%
P-glycoprotein substrate	+	0.5302	53.02%
CYP3A4 substrate	+	0.7189	71.89%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8331	83.31%
CYP3A4 inhibition	-	0.8153	81.53%
CYP2C9 inhibition	-	0.8962	89.62%
CYP2C19 inhibition	-	0.8944	89.44%
CYP2D6 inhibition	-	0.9249	92.49%
CYP1A2 inhibition	-	0.9071	90.71%
CYP2C8 inhibition	+	0.6297	62.97%
CYP inhibitory promiscuity	-	0.8831	88.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4991	49.91%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9073	90.73%
Skin irritation	+	0.5198	51.98%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8292	82.92%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6884	68.84%
skin sensitisation	-	0.9194	91.94%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7131	71.31%
Acute Oral Toxicity (c)	III	0.4540	45.40%
Estrogen receptor binding	+	0.8446	84.46%
Androgen receptor binding	+	0.6952	69.52%
Thyroid receptor binding	-	0.5166	51.66%
Glucocorticoid receptor binding	+	0.6623	66.23%
Aromatase binding	+	0.6872	68.72%
PPAR gamma	+	0.7833	78.33%
Honey bee toxicity	-	0.6808	68.08%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9433	94.33%

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	98.37%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.54%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.72%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.67%	97.25%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	95.62%	94.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.55%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.51%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.79%	95.89%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	91.64%	92.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.20%	92.62%
CHEMBL226	P30542	Adenosine A1 receptor	89.89%	95.93%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.92%	93.56%
CHEMBL1937	Q92769	Histone deacetylase 2	88.64%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.60%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.19%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.43%	96.21%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.73%	97.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.39%	96.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.49%	94.00%
CHEMBL237	P41145	Kappa opioid receptor	84.10%	98.10%
CHEMBL3401	O75469	Pregnane X receptor	82.07%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.46%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.48%	89.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.41%	96.90%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.34%	94.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.20%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.20%	94.08%

Plants that contains it

• Ajuga salicifolia

Cross-Links

• PubChem: 11018473
• LOTUS: LTS0014685
• wikiData: Q104667494