[(2S,3R,4S,5R,6R)-2-[[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (Z)-3-methylpent-2-enoate

Details

• Internal ID: 0c0bcbe7-b508-42fe-a85f-b5bf1df56cc8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(2S,3R,4S,5R,6R)-2-[[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl] (Z)-3-methylpent-2-enoate
• SMILES (Canonical): CCC(=CC(=O)OC1C(C(C(OC1OC2(CCC3C(C3(C)C)C4C2CCC4C)C)C)O)O)C
• SMILES (Isomeric): CC/C(=C\C(=O)O[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@@]2(CC[C@@H]3[C@@H](C3(C)C)[C@H]4[C@@H]2CC[C@H]4C)C)C)O)O)/C
• InChI: InChI=1S/C27H44O6/c1-8-14(2)13-19(28)32-24-23(30)22(29)16(4)31-25(24)33-27(7)12-11-18-21(26(18,5)6)20-15(3)9-10-17(20)27/h13,15-18,20-25,29-30H,8-12H2,1-7H3/b14-13-/t15-,16-,17+,18-,20-,21-,22+,23+,24-,25+,27-/m1/s1
• InChI Key: UQUYXFBISSCISA-IFPHDOPMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₆
• Molecular Weight: 464.60 g/mol
• Exact Mass: 464.31378912 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.22
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9650	96.50%
Caco-2	-	0.6646	66.46%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6312	63.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8553	85.53%
OATP1B3 inhibitior	+	0.9287	92.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8376	83.76%
P-glycoprotein inhibitior	-	0.4327	43.27%
P-glycoprotein substrate	-	0.6032	60.32%
CYP3A4 substrate	+	0.7178	71.78%
CYP2C9 substrate	-	0.7952	79.52%
CYP2D6 substrate	-	0.8967	89.67%
CYP3A4 inhibition	-	0.7618	76.18%
CYP2C9 inhibition	-	0.6474	64.74%
CYP2C19 inhibition	-	0.6494	64.94%
CYP2D6 inhibition	-	0.9273	92.73%
CYP1A2 inhibition	-	0.5990	59.90%
CYP2C8 inhibition	+	0.6361	63.61%
CYP inhibitory promiscuity	-	0.8690	86.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6720	67.20%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9493	94.93%
Skin irritation	-	0.5610	56.10%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.7453	74.53%
Human Ether-a-go-go-Related Gene inhibition	-	0.4908	49.08%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5316	53.16%
skin sensitisation	-	0.7336	73.36%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8045	80.45%
Acute Oral Toxicity (c)	III	0.3848	38.48%
Estrogen receptor binding	+	0.7821	78.21%
Androgen receptor binding	+	0.6003	60.03%
Thyroid receptor binding	+	0.5284	52.84%
Glucocorticoid receptor binding	+	0.6642	66.42%
Aromatase binding	+	0.7379	73.79%
PPAR gamma	+	0.6608	66.08%
Honey bee toxicity	-	0.5624	56.24%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6245	62.45%
Fish aquatic toxicity	+	0.9849	98.49%

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	98.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.27%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.92%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	93.34%	90.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.18%	96.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.43%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	90.81%	91.19%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.31%	89.34%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	90.00%	89.05%
CHEMBL226	P30542	Adenosine A1 receptor	89.43%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.47%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.42%	94.80%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.26%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.14%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.88%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.68%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.72%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	84.92%	92.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.56%	94.45%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.33%	89.50%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	83.92%	97.31%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.22%	95.50%
CHEMBL4040	P28482	MAP kinase ERK2	81.55%	83.82%
CHEMBL5957	P21589	5'-nucleotidase	81.53%	97.78%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.48%	92.62%

Plants that contains it

• Calendula arvensis

Cross-Links

• PubChem: 44567061
• LOTUS: LTS0104878
• wikiData: Q105277467