[(4R,5S,8R,8aS)-8a-hydroxy-3,8-dimethyl-2-oxo-5-prop-1-en-2-yl-1,4,5,6,7,8-hexahydroazulen-4-yl] acetate

Details

• Internal ID: afa3891e-26ea-4e4e-b72d-aa4a8c5feb30
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: [(4R,5S,8R,8aS)-8a-hydroxy-3,8-dimethyl-2-oxo-5-prop-1-en-2-yl-1,4,5,6,7,8-hexahydroazulen-4-yl] acetate
• SMILES (Canonical): CC1CCC(C(C2=C(C(=O)CC12O)C)OC(=O)C)C(=C)C
• SMILES (Isomeric): C[C@@H]1CC[C@H]([C@H](C2=C(C(=O)C[C@]12O)C)OC(=O)C)C(=C)C
• InChI: InChI=1S/C17H24O4/c1-9(2)13-7-6-10(3)17(20)8-14(19)11(4)15(17)16(13)21-12(5)18/h10,13,16,20H,1,6-8H2,2-5H3/t10-,13+,16-,17+/m1/s1
• InChI Key: VCJVMBMZJBVIHJ-SDNRIPMJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.40 g/mol
• Exact Mass: 292.16745924 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.56
• 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	+	0.9878	98.78%
Caco-2	+	0.7167	71.67%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7356	73.56%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9437	94.37%
OATP1B3 inhibitior	+	0.7990	79.90%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7342	73.42%
BSEP inhibitior	-	0.7701	77.01%
P-glycoprotein inhibitior	-	0.7850	78.50%
P-glycoprotein substrate	-	0.7404	74.04%
CYP3A4 substrate	+	0.6225	62.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9113	91.13%
CYP3A4 inhibition	-	0.8190	81.90%
CYP2C9 inhibition	-	0.6454	64.54%
CYP2C19 inhibition	-	0.7259	72.59%
CYP2D6 inhibition	-	0.9557	95.57%
CYP1A2 inhibition	+	0.5684	56.84%
CYP2C8 inhibition	-	0.8100	81.00%
CYP inhibitory promiscuity	-	0.9748	97.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6188	61.88%
Eye corrosion	-	0.9860	98.60%
Eye irritation	+	0.5764	57.64%
Skin irritation	+	0.6438	64.38%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5330	53.30%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5425	54.25%
skin sensitisation	-	0.7969	79.69%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5449	54.49%
Acute Oral Toxicity (c)	II	0.4021	40.21%
Estrogen receptor binding	-	0.5433	54.33%
Androgen receptor binding	-	0.6292	62.92%
Thyroid receptor binding	+	0.5403	54.03%
Glucocorticoid receptor binding	-	0.5673	56.73%
Aromatase binding	-	0.7393	73.93%
PPAR gamma	-	0.6149	61.49%
Honey bee toxicity	-	0.7802	78.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9952	99.52%

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	94.14%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.92%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.83%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.56%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.25%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.92%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.35%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.14%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.10%	96.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.62%	97.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.27%	94.80%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.66%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.99%	89.00%

Plants that contains it

• Pleocarphus revolutus

Cross-Links

• PubChem: 14081862
• LOTUS: LTS0200680
• wikiData: Q105283738