(3aR,5S,5aS,7S,9aR)-7-hydroxy-5,8-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 0b164fa9-4739-4f8a-923b-bd63fd051f13
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aR,5S,5aS,7S,9aR)-7-hydroxy-5,8-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1CC2C(CC3=C(C(CC13)O)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@H](CC3=C([C@H](C[C@@H]13)O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O3/c1-7-4-14-12(9(3)15(17)18-14)5-11-8(2)13(16)6-10(7)11/h7,10,12-14,16H,3-6H2,1-2H3/t7-,10-,12+,13-,14+/m0/s1
• InChI Key: QVHUJSOXRFYJFA-CWVGPJTRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.8329	83.29%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5244	52.44%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.8999	89.99%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9444	94.44%
P-glycoprotein inhibitior	-	0.9050	90.50%
P-glycoprotein substrate	-	0.8464	84.64%
CYP3A4 substrate	+	0.5471	54.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.7398	73.98%
CYP2C9 inhibition	-	0.8935	89.35%
CYP2C19 inhibition	-	0.8086	80.86%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.5299	52.99%
CYP2C8 inhibition	-	0.8058	80.58%
CYP inhibitory promiscuity	-	0.9217	92.17%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9417	94.17%
Carcinogenicity (trinary)	Non-required	0.5752	57.52%
Eye corrosion	-	0.9635	96.35%
Eye irritation	-	0.5340	53.40%
Skin irritation	-	0.5377	53.77%
Skin corrosion	-	0.9145	91.45%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6532	65.32%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.6371	63.71%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6966	69.66%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6470	64.70%
Acute Oral Toxicity (c)	III	0.4392	43.92%
Estrogen receptor binding	+	0.6158	61.58%
Androgen receptor binding	-	0.5141	51.41%
Thyroid receptor binding	-	0.6030	60.30%
Glucocorticoid receptor binding	-	0.4724	47.24%
Aromatase binding	-	0.6490	64.90%
PPAR gamma	-	0.6097	60.97%
Honey bee toxicity	-	0.7244	72.44%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9900	99.00%

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	91.99%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.75%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.69%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.05%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.83%	98.95%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.59%	86.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.59%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.36%	92.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.01%	93.56%

Plants that contains it

• Stevia polyphylla

Cross-Links

• PubChem: 162885021
• LOTUS: LTS0095152
• wikiData: Q105228668