methyl 2-[(5S,6R,8S,8aS)-6-acetyloxy-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-enoate

Details

• Internal ID: 478b2396-036f-429d-8b0e-891c6b438fb5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: methyl 2-[(5S,6R,8S,8aS)-6-acetyloxy-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-enoate
• SMILES (Canonical): CC1CC(C(CC2=C(CCC12)C)C(=C)C(=O)OC)OC(=O)C
• SMILES (Isomeric): C[C@H]1C[C@H]([C@@H](CC2=C(CC[C@@H]12)C)C(=C)C(=O)OC)OC(=O)C
• InChI: InChI=1S/C18H26O4/c1-10-6-7-14-11(2)8-17(22-13(4)19)16(9-15(10)14)12(3)18(20)21-5/h11,14,16-17H,3,6-9H2,1-2,4-5H3/t11-,14-,16-,17+/m0/s1
• InChI Key: ASTWPPMWLUBJIR-YJOCZYATSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.18310931 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9907	99.07%
Caco-2	+	0.8496	84.96%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6789	67.89%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9192	91.92%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6619	66.19%
P-glycoprotein inhibitior	-	0.7018	70.18%
P-glycoprotein substrate	-	0.7035	70.35%
CYP3A4 substrate	+	0.6421	64.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8813	88.13%
CYP3A4 inhibition	-	0.7960	79.60%
CYP2C9 inhibition	-	0.8108	81.08%
CYP2C19 inhibition	-	0.8297	82.97%
CYP2D6 inhibition	-	0.9394	93.94%
CYP1A2 inhibition	-	0.6150	61.50%
CYP2C8 inhibition	-	0.6490	64.90%
CYP inhibitory promiscuity	-	0.9528	95.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6963	69.63%
Eye corrosion	-	0.9744	97.44%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.6383	63.83%
Skin corrosion	-	0.9727	97.27%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5352	53.52%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5211	52.11%
skin sensitisation	-	0.7650	76.50%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6004	60.04%
Acute Oral Toxicity (c)	III	0.6038	60.38%
Estrogen receptor binding	+	0.5387	53.87%
Androgen receptor binding	+	0.5502	55.02%
Thyroid receptor binding	-	0.5199	51.99%
Glucocorticoid receptor binding	+	0.6281	62.81%
Aromatase binding	-	0.7645	76.45%
PPAR gamma	-	0.4921	49.21%
Honey bee toxicity	-	0.7352	73.52%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9954	99.54%

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	95.01%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.78%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.89%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	89.53%	91.19%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.42%	94.80%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.67%	94.33%
CHEMBL2581	P07339	Cathepsin D	82.89%	98.95%
CHEMBL5028	O14672	ADAM10	82.54%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.31%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.75%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.25%	97.09%

Plants that contains it

• Ozothamnus adnatus

Cross-Links

• PubChem: 163029487
• LOTUS: LTS0259467
• wikiData: Q104918062