[(1S,2S,3S,4S,5S,6S)-2-acetyloxy-5-hydroxy-4-[(3S,5S)-6-hydroxy-6-methyl-3,5-bis(2-methylpropanoyloxy)hept-1-en-2-yl]-1-methyl-7-oxabicyclo[4.1.0]heptan-3-yl] 2-methylpropanoate

Details

• Internal ID: 535779b7-9d5f-4f7c-b3a7-e956836310d0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2S,3S,4S,5S,6S)-2-acetyloxy-5-hydroxy-4-[(3S,5S)-6-hydroxy-6-methyl-3,5-bis(2-methylpropanoyloxy)hept-1-en-2-yl]-1-methyl-7-oxabicyclo[4.1.0]heptan-3-yl] 2-methylpropanoate
• SMILES (Canonical): CC(C)C(=O)OC1C(C(C2C(C1OC(=O)C)(O2)C)O)C(=C)C(CC(C(C)(C)O)OC(=O)C(C)C)OC(=O)C(C)C
• SMILES (Isomeric): CC(C)C(=O)O[C@H]1[C@H]([C@@H]([C@H]2[C@@]([C@H]1OC(=O)C)(O2)C)O)C(=C)[C@H](C[C@@H](C(C)(C)O)OC(=O)C(C)C)OC(=O)C(C)C
• InChI: InChI=1S/C29H46O11/c1-13(2)25(32)37-18(12-19(28(9,10)35)38-26(33)14(3)4)16(7)20-21(31)23-29(11,40-23)24(36-17(8)30)22(20)39-27(34)15(5)6/h13-15,18-24,31,35H,7,12H2,1-6,8-11H3/t18-,19-,20-,21-,22-,23-,24-,29-/m0/s1
• InChI Key: DWPSFGXEANDQTF-ZBBYIXHASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₆O₁₁
• Molecular Weight: 570.70 g/mol
• Exact Mass: 570.30401228 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.49
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9562	95.62%
Caco-2	-	0.7942	79.42%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6983	69.83%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	+	0.9094	90.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6425	64.25%
P-glycoprotein inhibitior	+	0.7247	72.47%
P-glycoprotein substrate	-	0.5968	59.68%
CYP3A4 substrate	+	0.6609	66.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8561	85.61%
CYP3A4 inhibition	-	0.8334	83.34%
CYP2C9 inhibition	-	0.8459	84.59%
CYP2C19 inhibition	-	0.7521	75.21%
CYP2D6 inhibition	-	0.9189	91.89%
CYP1A2 inhibition	-	0.9047	90.47%
CYP2C8 inhibition	-	0.5945	59.45%
CYP inhibitory promiscuity	-	0.9268	92.68%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8859	88.59%
Carcinogenicity (trinary)	Non-required	0.6337	63.37%
Eye corrosion	-	0.9736	97.36%
Eye irritation	-	0.8751	87.51%
Skin irritation	-	0.6397	63.97%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5934	59.34%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	+	0.6431	64.31%
skin sensitisation	-	0.5439	54.39%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.8079	80.79%
Acute Oral Toxicity (c)	III	0.4366	43.66%
Estrogen receptor binding	+	0.7696	76.96%
Androgen receptor binding	+	0.5559	55.59%
Thyroid receptor binding	+	0.5393	53.93%
Glucocorticoid receptor binding	+	0.6879	68.79%
Aromatase binding	+	0.6504	65.04%
PPAR gamma	+	0.6674	66.74%
Honey bee toxicity	-	0.5154	51.54%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9709	97.09%

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	98.79%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.00%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.89%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.23%	98.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	94.03%	96.47%
CHEMBL2996	Q05655	Protein kinase C delta	92.79%	97.79%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.09%	95.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.79%	96.77%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.14%	96.61%
CHEMBL299	P17252	Protein kinase C alpha	89.76%	98.03%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.72%	82.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.53%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	87.99%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	87.39%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	87.13%	91.19%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.75%	98.75%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.67%	97.28%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.13%	89.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.09%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.93%	94.45%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.61%	95.71%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.94%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.37%	94.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.31%	92.62%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.26%	95.71%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.59%	97.29%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.04%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.25%	99.23%

Plants that contains it

• Cremanthodium ellisii

Cross-Links

• PubChem: 163043246
• LOTUS: LTS0004465
• wikiData: Q104990683