[(4S,4aS,5R,8aR)-6-hydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-4-yl] acetate

Details

• Internal ID: 253249bf-7799-4e85-8af7-a656b65ca033
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aS,5R,8aR)-6-hydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-4-yl] acetate
• SMILES (Canonical): CC1C(CCC2C1(C(C3=C(C2)OC=C3C)OC(=O)C)C)O
• SMILES (Isomeric): C[C@H]1C(CC[C@H]2[C@@]1([C@@H](C3=C(C2)OC=C3C)OC(=O)C)C)O
• InChI: InChI=1S/C17H24O4/c1-9-8-20-14-7-12-5-6-13(19)10(2)17(12,4)16(15(9)14)21-11(3)18/h8,10,12-13,16,19H,5-7H2,1-4H3/t10-,12+,13?,16+,17+/m0/s1
• InChI Key: CXZIQFLLAXJLDS-GPXYYQMSSA-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): 59.70 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.16
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.7146	71.46%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7122	71.22%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.8999	89.99%
OATP1B3 inhibitior	+	0.9045	90.45%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8559	85.59%
P-glycoprotein inhibitior	-	0.8209	82.09%
P-glycoprotein substrate	-	0.7455	74.55%
CYP3A4 substrate	+	0.6405	64.05%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.7929	79.29%
CYP3A4 inhibition	-	0.6739	67.39%
CYP2C9 inhibition	-	0.7784	77.84%
CYP2C19 inhibition	-	0.8125	81.25%
CYP2D6 inhibition	-	0.9568	95.68%
CYP1A2 inhibition	-	0.6471	64.71%
CYP2C8 inhibition	-	0.6370	63.70%
CYP inhibitory promiscuity	-	0.9252	92.52%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5608	56.08%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9799	97.99%
Skin irritation	-	0.6116	61.16%
Skin corrosion	-	0.8963	89.63%
Ames mutagenesis	-	0.6464	64.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5805	58.05%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5087	50.87%
skin sensitisation	-	0.8673	86.73%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7477	74.77%
Acute Oral Toxicity (c)	III	0.4439	44.39%
Estrogen receptor binding	+	0.6851	68.51%
Androgen receptor binding	+	0.6019	60.19%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7325	73.25%
Aromatase binding	+	0.5254	52.54%
PPAR gamma	+	0.5991	59.91%
Honey bee toxicity	-	0.7895	78.95%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9628	96.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.51%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.49%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.22%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.21%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.42%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.21%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.87%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.72%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.43%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.70%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.61%	92.94%

Plants that contains it

• Petasites japonicus

Cross-Links

• PubChem: 5315813
• NPASS: NPC175185