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

Details

• Internal ID: 896672ed-8a6f-4dfc-ac73-c3f6f2e3a4c0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2S,3S,5R)-3-ethyl-5-[(1S)-1-[(3R,5R,9R,10S,13S,14R,16S,17R)-16-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]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)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)C)O
• InChI: InChI=1S/C41H68O14/c1-6-20-14-27(55-41(20,5)18-51-37-35(49)33(47)31(45)28(16-42)53-37)19(2)30-26(44)15-25-23-8-7-21-13-22(9-11-39(21,3)24(23)10-12-40(25,30)4)52-38-36(50)34(48)32(46)29(17-43)54-38/h8,19-22,24-38,42-50H,6-7,9-18H2,1-5H3/t19-,20+,21-,22-,24+,25+,26+,27-,28-,29-,30+,31-,32-,33+,34+,35-,36-,37-,38-,39+,40+,41-/m1/s1
• InChI Key: PNCRVCCFEFPNAG-XELRMEGCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₈O₁₄
• Molecular Weight: 785.00 g/mol
• Exact Mass: 784.46090684 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 10

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	-	0.8780	87.80%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6786	67.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8560	85.60%
OATP1B3 inhibitior	+	0.9092	90.92%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.6415	64.15%
P-glycoprotein inhibitior	+	0.7251	72.51%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7086	70.86%
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	+	0.5841	58.41%
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	-	0.9163	91.63%
Skin irritation	+	0.5198	51.98%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8381	83.81%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6759	67.59%
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	-	0.7094	70.94%
Acute Oral Toxicity (c)	III	0.4540	45.40%
Estrogen receptor binding	+	0.7700	77.00%
Androgen receptor binding	+	0.6696	66.96%
Thyroid receptor binding	-	0.5894	58.94%
Glucocorticoid receptor binding	+	0.5714	57.14%
Aromatase binding	+	0.6460	64.60%
PPAR gamma	+	0.7140	71.40%
Honey bee toxicity	-	0.7183	71.83%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
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	98.28%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.70%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.17%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.07%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.03%	96.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	95.67%	94.23%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.68%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.29%	95.89%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.28%	92.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.20%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.60%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.20%	96.21%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.90%	93.56%
CHEMBL226	P30542	Adenosine A1 receptor	87.49%	95.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.15%	95.50%
CHEMBL237	P41145	Kappa opioid receptor	85.10%	98.10%
CHEMBL1937	Q92769	Histone deacetylase 2	84.12%	94.75%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.51%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.18%	94.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.08%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.24%	94.08%
CHEMBL221	P23219	Cyclooxygenase-1	80.67%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	80.55%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.05%	100.00%

Plants that contains it

• Ajuga salicifolia

Cross-Links

• PubChem: 10919842
• LOTUS: LTS0006983
• wikiData: Q104667623