methyl (1E,3S,5Z,8E)-3-acetyloxy-7-hydroxy-4,4,8-trimethylcycloundeca-1,5,8-triene-1-carboxylate

Details

• Internal ID: 92d26266-884e-4b2b-9021-dcf60a9c0f13
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl (1E,3S,5Z,8E)-3-acetyloxy-7-hydroxy-4,4,8-trimethylcycloundeca-1,5,8-triene-1-carboxylate
• SMILES (Canonical): CC1=CCCC(=CC(C(C=CC1O)(C)C)OC(=O)C)C(=O)OC
• SMILES (Isomeric): C/C/1=C\CC/C(=C\[C@@H](C(/C=C\C1O)(C)C)OC(=O)C)/C(=O)OC
• InChI: InChI=1S/C18H26O5/c1-12-7-6-8-14(17(21)22-5)11-16(23-13(2)19)18(3,4)10-9-15(12)20/h7,9-11,15-16,20H,6,8H2,1-5H3/b10-9-,12-7+,14-11+/t15?,16-/m0/s1
• InChI Key: PBHMEHISJHZTGB-DHQLSRFDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.17802393 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9718	97.18%
Caco-2	+	0.8532	85.32%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8021	80.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9098	90.98%
OATP1B3 inhibitior	+	0.9083	90.83%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5540	55.40%
P-glycoprotein inhibitior	-	0.6364	63.64%
P-glycoprotein substrate	-	0.7681	76.81%
CYP3A4 substrate	+	0.6555	65.55%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.9002	90.02%
CYP3A4 inhibition	-	0.8481	84.81%
CYP2C9 inhibition	-	0.7818	78.18%
CYP2C19 inhibition	-	0.8404	84.04%
CYP2D6 inhibition	-	0.8888	88.88%
CYP1A2 inhibition	-	0.6965	69.65%
CYP2C8 inhibition	-	0.7023	70.23%
CYP inhibitory promiscuity	-	0.9039	90.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7896	78.96%
Carcinogenicity (trinary)	Non-required	0.6541	65.41%
Eye corrosion	-	0.9701	97.01%
Eye irritation	-	0.7734	77.34%
Skin irritation	-	0.5221	52.21%
Skin corrosion	-	0.9528	95.28%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7041	70.41%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.5426	54.26%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6226	62.26%
Acute Oral Toxicity (c)	III	0.7221	72.21%
Estrogen receptor binding	+	0.6215	62.15%
Androgen receptor binding	-	0.7361	73.61%
Thyroid receptor binding	-	0.6143	61.43%
Glucocorticoid receptor binding	+	0.6329	63.29%
Aromatase binding	-	0.5986	59.86%
PPAR gamma	-	0.5312	53.12%
Honey bee toxicity	-	0.7510	75.10%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9394	93.94%

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	97.93%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.43%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.74%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.71%	94.45%
CHEMBL2581	P07339	Cathepsin D	86.93%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	86.40%	91.19%
CHEMBL5028	O14672	ADAM10	83.73%	97.50%
CHEMBL4208	P20618	Proteasome component C5	82.76%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.66%	95.56%

Plants that contains it

• Asteriscus graveolens

Cross-Links

• PubChem: 162817338
• LOTUS: LTS0270234
• wikiData: Q105205198