(3aS,5R,6S,7aS)-6-[(2E,4S)-4-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-3,7-dimethylocta-2,6-dienyl]-6-hydroxy-5-[(1E,3R)-3-hydroxy-2,6-dimethylhepta-1,5-dienyl]-3a-methyl-7-methylidene-2,3,5,7a-tetrahydro-1H-inden-4-one

Details

• Internal ID: 8715b7ec-ea75-4583-bcb8-bdfd653860c8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3aS,5R,6S,7aS)-6-[(2E,4S)-4-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-3,7-dimethylocta-2,6-dienyl]-6-hydroxy-5-[(1E,3R)-3-hydroxy-2,6-dimethylhepta-1,5-dienyl]-3a-methyl-7-methylidene-2,3,5,7a-tetrahydro-1H-inden-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)OC(CC=C(C)C)C(=CCC4(C(C(=O)C5(CCCC5C4=C)C)C=C(C)C(CC=C(C)C)O)O)C)C)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H](O[C@H]([C@@H]([C@@H]2O)O)O[C@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O[C@@H](CC=C(C)C)/C(=C/C[C@@]4([C@H](C(=O)[C@]5(CCC[C@H]5C4=C)C)/C=C(\C)/[C@@H](CC=C(C)C)O)O)/C)C)C)O)O)O
• InChI: InChI=1S/C48H76O16/c1-22(2)14-16-32(49)25(6)21-31-43(57)47(11)19-12-13-30(47)26(7)48(31,58)20-18-24(5)33(17-15-23(3)4)62-44-39(55)36(52)41(28(9)60-44)64-46-40(56)37(53)42(29(10)61-46)63-45-38(54)35(51)34(50)27(8)59-45/h14-15,18,21,27-42,44-46,49-56,58H,7,12-13,16-17,19-20H2,1-6,8-11H3/b24-18+,25-21+/t27-,28+,29-,30-,31-,32+,33-,34-,35+,36+,37-,38+,39+,40+,41-,42-,44-,45-,46-,47-,48+/m0/s1
• InChI Key: LFDOYTXWKJWMOB-KTCJVHAPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₆O₁₆
• Molecular Weight: 909.10 g/mol
• Exact Mass: 908.51333633 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8498	84.98%
Caco-2	-	0.8733	87.33%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6673	66.73%
OATP2B1 inhibitior	-	0.8712	87.12%
OATP1B1 inhibitior	+	0.8683	86.83%
OATP1B3 inhibitior	-	0.2286	22.86%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9395	93.95%
P-glycoprotein inhibitior	+	0.7441	74.41%
P-glycoprotein substrate	+	0.5374	53.74%
CYP3A4 substrate	+	0.7123	71.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8661	86.61%
CYP3A4 inhibition	-	0.7618	76.18%
CYP2C9 inhibition	-	0.8725	87.25%
CYP2C19 inhibition	-	0.8618	86.18%
CYP2D6 inhibition	-	0.9338	93.38%
CYP1A2 inhibition	-	0.8724	87.24%
CYP2C8 inhibition	+	0.5736	57.36%
CYP inhibitory promiscuity	-	0.9129	91.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6442	64.42%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9051	90.51%
Skin irritation	+	0.5955	59.55%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7379	73.79%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5528	55.28%
skin sensitisation	-	0.8155	81.55%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6071	60.71%
Acute Oral Toxicity (c)	I	0.5148	51.48%
Estrogen receptor binding	+	0.8402	84.02%
Androgen receptor binding	+	0.6822	68.22%
Thyroid receptor binding	+	0.5548	55.48%
Glucocorticoid receptor binding	+	0.7984	79.84%
Aromatase binding	+	0.6574	65.74%
PPAR gamma	+	0.8163	81.63%
Honey bee toxicity	-	0.5989	59.89%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9867	98.67%

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	98.93%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.55%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.30%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.57%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.97%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.87%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.40%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.36%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.35%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.10%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.03%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.89%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.47%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	85.05%	95.93%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.22%	92.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.47%	100.00%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	83.44%	92.78%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.61%	91.07%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.59%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.62%	95.83%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.61%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162966375
• LOTUS: LTS0159577
• wikiData: Q105150965