(2S,3R,4S,5R,6R)-2-[[(1S,1aR,4R,4aS,7R,7aS,7bS)-1,4,7-trimethyl-1-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-6-methyloxane-3,4,5-triol

Details

• Internal ID: c9c149e1-6315-4bc1-8d97-89cfd90b6772
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S,5R,6R)-2-[[(1S,1aR,4R,4aS,7R,7aS,7bS)-1,4,7-trimethyl-1-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2C1C3C(C3(C)COC4C(C(C(C(O4)CO)O)O)O)CCC2(C)OC5C(C(C(C(O5)C)O)O)O
• SMILES (Isomeric): C[C@@H]1CC[C@H]2[C@@H]1[C@H]3[C@H]([C@]3(C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)CC[C@@]2(C)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)C)O)O)O
• InChI: InChI=1S/C27H46O11/c1-11-5-6-13-16(11)17-14(7-8-27(13,4)38-25-23(34)20(31)18(29)12(2)36-25)26(17,3)10-35-24-22(33)21(32)19(30)15(9-28)37-24/h11-25,28-34H,5-10H2,1-4H3/t11-,12-,13+,14-,15-,16-,17-,18+,19-,20+,21+,22-,23-,24-,25+,26+,27-/m1/s1
• InChI Key: QMZPCWAILBCLFF-JGVVKRRYSA-N
• Popularity: 2 references 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: -0.20
• Atomic LogP (AlogP): -0.89
• 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	-	0.6188	61.88%
Caco-2	-	0.8592	85.92%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6018	60.18%
OATP2B1 inhibitior	-	0.7255	72.55%
OATP1B1 inhibitior	+	0.8785	87.85%
OATP1B3 inhibitior	+	0.9287	92.87%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.9278	92.78%
P-glycoprotein inhibitior	-	0.5482	54.82%
P-glycoprotein substrate	-	0.7702	77.02%
CYP3A4 substrate	+	0.6792	67.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8203	82.03%
CYP3A4 inhibition	-	0.9674	96.74%
CYP2C9 inhibition	-	0.8419	84.19%
CYP2C19 inhibition	-	0.8250	82.50%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.8701	87.01%
CYP2C8 inhibition	+	0.5163	51.63%
CYP inhibitory promiscuity	-	0.9431	94.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6917	69.17%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9272	92.72%
Skin irritation	-	0.7271	72.71%
Skin corrosion	-	0.9510	95.10%
Ames mutagenesis	-	0.7307	73.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.6684	66.84%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7372	73.72%
skin sensitisation	-	0.9300	93.00%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8690	86.90%
Acute Oral Toxicity (c)	I	0.6262	62.62%
Estrogen receptor binding	+	0.6023	60.23%
Androgen receptor binding	+	0.5736	57.36%
Thyroid receptor binding	-	0.4907	49.07%
Glucocorticoid receptor binding	-	0.4779	47.79%
Aromatase binding	+	0.6467	64.67%
PPAR gamma	+	0.6104	61.04%
Honey bee toxicity	-	0.6627	66.27%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8141	81.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.49%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.31%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.97%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	94.50%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.81%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.62%	97.25%
CHEMBL237	P41145	Kappa opioid receptor	88.91%	98.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.53%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.07%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.86%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.67%	96.38%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.17%	97.53%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.51%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.30%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	83.62%	94.75%
CHEMBL233	P35372	Mu opioid receptor	83.28%	97.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.93%	96.77%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.28%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.97%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.84%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.56%	96.21%

Plants that contains it

• Calendula officinalis

Cross-Links

• PubChem: 10951715
• NPASS: NPC193585
• LOTUS: LTS0242391
• wikiData: Q105224276