[(1R,2S,3S,4R,6R,7S,8S,9S,10R)-9-acetyloxy-6,7-dihydroxy-1,7-dimethyl-2,8-bis[[(Z)-2-methylbut-2-enoyl]oxy]-4-prop-1-en-2-yl-11-oxabicyclo[8.1.0]undecan-3-yl] (2R)-2-methylbutanoate

Details

• Internal ID: e8cee4ae-9416-4297-9bed-39afb061e043
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,2S,3S,4R,6R,7S,8S,9S,10R)-9-acetyloxy-6,7-dihydroxy-1,7-dimethyl-2,8-bis[[(Z)-2-methylbut-2-enoyl]oxy]-4-prop-1-en-2-yl-11-oxabicyclo[8.1.0]undecan-3-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(CC(C(C(C(C2C(C1OC(=O)C(=CC)C)(O2)C)OC(=O)C)OC(=O)C(=CC)C)(C)O)O)C(=C)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@H](C[C@H]([C@]([C@H]([C@H]([C@@H]2[C@]([C@H]1OC(=O)/C(=C\C)/C)(O2)C)OC(=O)C)OC(=O)/C(=C\C)/C)(C)O)O)C(=C)C
• InChI: InChI=1S/C32H48O11/c1-12-17(6)28(35)40-23-21(16(4)5)15-22(34)31(10,38)25(41-29(36)18(7)13-2)24(39-20(9)33)27-32(11,43-27)26(23)42-30(37)19(8)14-3/h13-14,17,21-27,34,38H,4,12,15H2,1-3,5-11H3/b18-13-,19-14-/t17-,21-,22-,23+,24-,25+,26+,27-,31+,32+/m1/s1
• InChI Key: KFQZVOVQZZCJFE-REHWUINFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₁₁
• Molecular Weight: 608.70 g/mol
• Exact Mass: 608.31966234 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9749	97.49%
Caco-2	-	0.8008	80.08%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4847	48.47%
OATP2B1 inhibitior	-	0.7156	71.56%
OATP1B1 inhibitior	+	0.8705	87.05%
OATP1B3 inhibitior	+	0.9311	93.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9278	92.78%
P-glycoprotein inhibitior	+	0.8161	81.61%
P-glycoprotein substrate	-	0.5515	55.15%
CYP3A4 substrate	+	0.6655	66.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8938	89.38%
CYP3A4 inhibition	+	0.5517	55.17%
CYP2C9 inhibition	-	0.8156	81.56%
CYP2C19 inhibition	-	0.7315	73.15%
CYP2D6 inhibition	-	0.9243	92.43%
CYP1A2 inhibition	-	0.8062	80.62%
CYP2C8 inhibition	-	0.6510	65.10%
CYP inhibitory promiscuity	-	0.9589	95.89%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9043	90.43%
Carcinogenicity (trinary)	Non-required	0.6067	60.67%
Eye corrosion	-	0.9778	97.78%
Eye irritation	-	0.9044	90.44%
Skin irritation	-	0.6120	61.20%
Skin corrosion	-	0.9011	90.11%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5927	59.27%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.6076	60.76%
skin sensitisation	-	0.6878	68.78%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.4579	45.79%
Acute Oral Toxicity (c)	III	0.4682	46.82%
Estrogen receptor binding	+	0.7232	72.32%
Androgen receptor binding	+	0.6060	60.60%
Thyroid receptor binding	+	0.5257	52.57%
Glucocorticoid receptor binding	+	0.7241	72.41%
Aromatase binding	+	0.6479	64.79%
PPAR gamma	+	0.7050	70.50%
Honey bee toxicity	-	0.5672	56.72%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6555	65.55%
Fish aquatic toxicity	+	0.9660	96.60%

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	98.56%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.53%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.13%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	94.44%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	93.42%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.55%	91.11%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.84%	91.24%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	91.75%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.57%	96.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.54%	96.61%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	89.45%	97.47%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.27%	96.77%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.05%	96.47%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.99%	98.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.70%	93.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.66%	89.50%
CHEMBL2581	P07339	Cathepsin D	86.47%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	86.25%	97.79%
CHEMBL226	P30542	Adenosine A1 receptor	85.28%	95.93%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.94%	85.30%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.90%	92.62%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.88%	89.34%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.07%	89.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.41%	82.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.27%	96.90%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.10%	95.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.47%	95.50%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.49%	92.32%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.26%	97.29%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.20%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.07%	99.23%

Plants that contains it

• Kleinia fulgens

Cross-Links

• PubChem: 162917175
• LOTUS: LTS0158395
• wikiData: Q105140525