[(1R,3aR,4R,8aS)-8a-hydroxy-3a,6-dimethyl-3-oxo-1-propan-2-yl-2,4,7,8-tetrahydro-1H-azulen-4-yl] acetate

Details

• Internal ID: 4b74064a-5639-4588-84a0-1a6c3a256742
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,3aR,4R,8aS)-8a-hydroxy-3a,6-dimethyl-3-oxo-1-propan-2-yl-2,4,7,8-tetrahydro-1H-azulen-4-yl] acetate
• SMILES (Canonical): CC1=CC(C2(C(=O)CC(C2(CC1)O)C(C)C)C)OC(=O)C
• SMILES (Isomeric): CC1=C[C@H]([C@]2(C(=O)C[C@@H]([C@]2(CC1)O)C(C)C)C)OC(=O)C
• InChI: InChI=1S/C17H26O4/c1-10(2)13-9-14(19)16(5)15(21-12(4)18)8-11(3)6-7-17(13,16)20/h8,10,13,15,20H,6-7,9H2,1-5H3/t13-,15-,16-,17+/m1/s1
• InChI Key: NMFFRLYFDXSRFV-DZUCGIPZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.18310931 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 4
• 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	+	0.9886	98.86%
Caco-2	+	0.7747	77.47%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7656	76.56%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9213	92.13%
OATP1B3 inhibitior	+	0.7952	79.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7071	70.71%
BSEP inhibitior	-	0.8074	80.74%
P-glycoprotein inhibitior	-	0.7924	79.24%
P-glycoprotein substrate	-	0.7485	74.85%
CYP3A4 substrate	+	0.5891	58.91%
CYP2C9 substrate	-	0.8185	81.85%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.8373	83.73%
CYP2C9 inhibition	-	0.5242	52.42%
CYP2C19 inhibition	-	0.6913	69.13%
CYP2D6 inhibition	-	0.9590	95.90%
CYP1A2 inhibition	-	0.5177	51.77%
CYP2C8 inhibition	-	0.9076	90.76%
CYP inhibitory promiscuity	-	0.9646	96.46%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6173	61.73%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9058	90.58%
Skin irritation	+	0.6300	63.00%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6545	65.45%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5683	56.83%
skin sensitisation	-	0.7071	70.71%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.4641	46.41%
Acute Oral Toxicity (c)	II	0.4602	46.02%
Estrogen receptor binding	-	0.5638	56.38%
Androgen receptor binding	+	0.5963	59.63%
Thyroid receptor binding	-	0.5250	52.50%
Glucocorticoid receptor binding	-	0.5665	56.65%
Aromatase binding	-	0.5981	59.81%
PPAR gamma	-	0.6930	69.30%
Honey bee toxicity	-	0.7330	73.30%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9921	99.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.43%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.81%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.41%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.34%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.10%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.58%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	87.97%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.49%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.46%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.10%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	81.08%	91.19%

Plants that contains it

• Sium latifolium

Cross-Links

• PubChem: 162998932
• LOTUS: LTS0205016
• wikiData: Q105181737