(2S,3R,4S,5R,6R)-2-[2-[(2R,4aS,7S)-4a-methyl-8-methylidene-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-yloxy]-6-methyloxane-3,4,5-triol

Details

• Internal ID: 7432907f-4aba-4236-88b1-766e0e973671
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S,5R,6R)-2-[2-[(2R,4aS,7S)-4a-methyl-8-methylidene-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-yloxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC(C)(C)C2CCC3(CCC(C(=C)C3C2)OC4C(C(C(C(O4)CO)O)O)O)C)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC(C)(C)[C@@H]2CC[C@]3(CC[C@@H](C(=C)C3C2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C)O)O)O
• InChI: InChI=1S/C27H46O11/c1-12-15-10-14(26(3,4)38-25-23(34)20(31)18(29)13(2)35-25)6-8-27(15,5)9-7-16(12)36-24-22(33)21(32)19(30)17(11-28)37-24/h13-25,28-34H,1,6-11H2,2-5H3/t13-,14-,15?,16+,17-,18+,19-,20+,21+,22-,23-,24-,25+,27+/m1/s1
• InChI Key: OFIPMYQXNOJVMT-JVNRHACFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₆O₁₁
• Molecular Weight: 546.60 g/mol
• Exact Mass: 546.30401228 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.43
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6594	65.94%
Caco-2	-	0.8486	84.86%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7692	76.92%
OATP2B1 inhibitior	-	0.7257	72.57%
OATP1B1 inhibitior	+	0.8683	86.83%
OATP1B3 inhibitior	-	0.2989	29.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.8056	80.56%
P-glycoprotein inhibitior	-	0.5148	51.48%
P-glycoprotein substrate	-	0.7121	71.21%
CYP3A4 substrate	+	0.6785	67.85%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.8906	89.06%
CYP2C9 inhibition	-	0.8002	80.02%
CYP2C19 inhibition	-	0.8348	83.48%
CYP2D6 inhibition	-	0.9386	93.86%
CYP1A2 inhibition	-	0.8089	80.89%
CYP2C8 inhibition	+	0.5137	51.37%
CYP inhibitory promiscuity	-	0.9039	90.39%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7043	70.43%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9292	92.92%
Skin irritation	-	0.6218	62.18%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7192	71.92%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5476	54.76%
skin sensitisation	-	0.8848	88.48%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.7044	70.44%
Acute Oral Toxicity (c)	III	0.6898	68.98%
Estrogen receptor binding	+	0.5494	54.94%
Androgen receptor binding	+	0.5720	57.20%
Thyroid receptor binding	-	0.5373	53.73%
Glucocorticoid receptor binding	+	0.5618	56.18%
Aromatase binding	+	0.6049	60.49%
PPAR gamma	+	0.5777	57.77%
Honey bee toxicity	-	0.6594	65.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9745	97.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.07%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.86%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.60%	91.49%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.37%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.65%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.65%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.96%	92.94%
CHEMBL1871	P10275	Androgen Receptor	89.41%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.06%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.80%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.58%	100.00%
CHEMBL1977	P11473	Vitamin D receptor	85.16%	99.43%
CHEMBL1937	Q92769	Histone deacetylase 2	84.80%	94.75%
CHEMBL2996	Q05655	Protein kinase C delta	84.72%	97.79%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.28%	95.83%
CHEMBL2581	P07339	Cathepsin D	84.19%	98.95%
CHEMBL237	P41145	Kappa opioid receptor	83.71%	98.10%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.54%	86.92%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.15%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.98%	95.50%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	81.48%	97.31%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.61%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	80.44%	95.93%

Plants that contains it

• Calendula officinalis

Cross-Links

• PubChem: 10962618
• NPASS: NPC270280
• LOTUS: LTS0115978
• wikiData: Q105191097