(4aS,8aR)-4a,5,6,7,8a,9-Hexahydro-3,8a-dimethyl-5-methylenenaphtho[2,3-b]furan-8(4H)-one

Details

• Internal ID: 28086225-743d-438f-a1e9-f56765ccc2c3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4aS,8aR)-3,8a-dimethyl-5-methylidene-4a,6,7,9-tetrahydro-4H-benzo[f][1]benzofuran-8-one
• SMILES (Canonical): CC1=COC2=C1CC3C(=C)CCC(=O)C3(C2)C
• SMILES (Isomeric): CC1=COC2=C1C[C@H]3C(=C)CCC(=O)[C@@]3(C2)C
• InChI: InChI=1S/C15H18O2/c1-9-4-5-14(16)15(3)7-13-11(6-12(9)15)10(2)8-17-13/h8,12H,1,4-7H2,2-3H3/t12-,15+/m0/s1
• InChI Key: AKNPMCISDQNRFC-SWLSCSKDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.30 g/mol
• Exact Mass: 230.130679813 g/mol
• Topological Polar Surface Area (TPSA): 30.20 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• (4aS,8aR)-4a,5,6,7,8a,9-Hexahydro-3,8a-dimethyl-5-methylenenaphtho[2,3-b]furan-8(4H)-one
• 220289-78-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6752	67.52%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5257	52.57%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	+	0.9031	90.31%
OATP1B3 inhibitior	+	0.9206	92.06%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.8296	82.96%
P-glycoprotein inhibitior	-	0.9132	91.32%
P-glycoprotein substrate	-	0.9129	91.29%
CYP3A4 substrate	+	0.5420	54.20%
CYP2C9 substrate	-	0.7641	76.41%
CYP2D6 substrate	-	0.7521	75.21%
CYP3A4 inhibition	-	0.5181	51.81%
CYP2C9 inhibition	-	0.8536	85.36%
CYP2C19 inhibition	+	0.8064	80.64%
CYP2D6 inhibition	-	0.8950	89.50%
CYP1A2 inhibition	+	0.8365	83.65%
CYP2C8 inhibition	-	0.8477	84.77%
CYP inhibitory promiscuity	+	0.5176	51.76%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4753	47.53%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.5862	58.62%
Skin irritation	-	0.6222	62.22%
Skin corrosion	-	0.9516	95.16%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5714	57.14%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6892	68.92%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6253	62.53%
Acute Oral Toxicity (c)	III	0.6305	63.05%
Estrogen receptor binding	-	0.7486	74.86%
Androgen receptor binding	+	0.5571	55.71%
Thyroid receptor binding	-	0.5759	57.59%
Glucocorticoid receptor binding	-	0.5397	53.97%
Aromatase binding	-	0.6239	62.39%
PPAR gamma	+	0.6159	61.59%
Honey bee toxicity	-	0.8608	86.08%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9968	99.68%

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	94.71%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.43%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.66%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.40%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.33%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.66%	85.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.82%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.66%	94.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.40%	85.11%
CHEMBL2996	Q05655	Protein kinase C delta	81.23%	97.79%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.73%	93.40%

Plants that contains it

• Givotia madagascariensis
• Jatropha divaricata
• Phyllanthus oxyphyllus
• Smyrnium olusatrum

Cross-Links

• PubChem: 100927547
• LOTUS: LTS0156627
• wikiData: Q105240161