(4E,8S,9S)-5-methyl-8-prop-1-en-2-yl-10-oxabicyclo[7.2.1]dodeca-1(12),4-dien-11-one

Details

• Internal ID: 3d24fcd8-359e-4b20-a9f3-335b9c196d69
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4E,8S,9S)-5-methyl-8-prop-1-en-2-yl-10-oxabicyclo[7.2.1]dodeca-1(12),4-dien-11-one
• SMILES (Canonical): CC1=CCCC2=CC(C(CC1)C(=C)C)OC2=O
• SMILES (Isomeric): C/C/1=C\CCC2=C[C@@H]([C@@H](CC1)C(=C)C)OC2=O
• InChI: InChI=1S/C15H20O2/c1-10(2)13-8-7-11(3)5-4-6-12-9-14(13)17-15(12)16/h5,9,13-14H,1,4,6-8H2,2-3H3/b11-5+/t13-,14-/m0/s1
• InChI Key: FGWWKPRDQNGBKN-ZKZSOYRCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.55
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.8103	81.03%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Plasma membrane	0.3587	35.87%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9446	94.46%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7987	79.87%
P-glycoprotein inhibitior	-	0.9097	90.97%
P-glycoprotein substrate	-	0.9229	92.29%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.5839	58.39%
CYP2D6 substrate	-	0.8834	88.34%
CYP3A4 inhibition	-	0.7883	78.83%
CYP2C9 inhibition	-	0.8777	87.77%
CYP2C19 inhibition	-	0.6110	61.10%
CYP2D6 inhibition	-	0.9102	91.02%
CYP1A2 inhibition	+	0.8047	80.47%
CYP2C8 inhibition	-	0.8212	82.12%
CYP inhibitory promiscuity	-	0.8418	84.18%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5625	56.25%
Eye corrosion	-	0.7881	78.81%
Eye irritation	+	0.6217	62.17%
Skin irritation	-	0.5395	53.95%
Skin corrosion	-	0.9603	96.03%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6688	66.88%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	+	0.5942	59.42%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5308	53.08%
Acute Oral Toxicity (c)	III	0.6893	68.93%
Estrogen receptor binding	-	0.8607	86.07%
Androgen receptor binding	-	0.7103	71.03%
Thyroid receptor binding	-	0.7489	74.89%
Glucocorticoid receptor binding	-	0.6145	61.45%
Aromatase binding	-	0.8382	83.82%
PPAR gamma	-	0.6955	69.55%
Honey bee toxicity	-	0.8915	89.15%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9891	98.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.62%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.98%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.74%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.27%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.01%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.73%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.54%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.90%	96.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.53%	90.93%
CHEMBL3401	O75469	Pregnane X receptor	80.69%	94.73%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.56%	97.33%

Plants that contains it

• Aristolochia cucurbitifolia
• Aristolochia kaempferi

Cross-Links

• PubChem: 155559006
• LOTUS: LTS0097048
• wikiData: Q104995111