(3R,3aS,4S,9R,11aS)-4,9-dihydroxy-3,6-dimethyl-10-methylidene-3,3a,4,7,8,9,11,11a-octahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 8d30ae4b-4e59-4219-bba7-82c4c04dc6b3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3R,3aS,4S,9R,11aS)-4,9-dihydroxy-3,6-dimethyl-10-methylidene-3,3a,4,7,8,9,11,11a-octahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2C(CC(=C)C(CCC(=CC2O)C)O)OC1=O
• SMILES (Isomeric): C[C@@H]1[C@@H]2[C@H](CC(=C)[C@@H](CCC(=C[C@@H]2O)C)O)OC1=O
• InChI: InChI=1S/C15H22O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h6,10-14,16-17H,2,4-5,7H2,1,3H3/t10-,11-,12+,13+,14+/m1/s1
• InChI Key: AMBNTPYCDHUUJH-DGTMBMJNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9845	98.45%
Caco-2	+	0.6725	67.25%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6222	62.22%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9299	92.99%
OATP1B3 inhibitior	+	0.9140	91.40%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	-	0.9590	95.90%
P-glycoprotein inhibitior	-	0.9228	92.28%
P-glycoprotein substrate	-	0.8651	86.51%
CYP3A4 substrate	+	0.5560	55.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.6013	60.13%
CYP2C9 inhibition	-	0.9164	91.64%
CYP2C19 inhibition	-	0.8411	84.11%
CYP2D6 inhibition	-	0.9328	93.28%
CYP1A2 inhibition	+	0.5717	57.17%
CYP2C8 inhibition	-	0.9257	92.57%
CYP inhibitory promiscuity	-	0.9361	93.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5972	59.72%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.9585	95.85%
Skin irritation	-	0.5264	52.64%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6274	62.74%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.7829	78.29%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7521	75.21%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.7728	77.28%
Acute Oral Toxicity (c)	II	0.4020	40.20%
Estrogen receptor binding	-	0.6008	60.08%
Androgen receptor binding	-	0.5775	57.75%
Thyroid receptor binding	-	0.5052	50.52%
Glucocorticoid receptor binding	+	0.5650	56.50%
Aromatase binding	-	0.7573	75.73%
PPAR gamma	-	0.6577	65.77%
Honey bee toxicity	-	0.8886	88.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9861	98.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.60%	94.80%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	92.75%	86.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.85%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.03%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.72%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.14%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.09%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.41%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.82%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.74%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.74%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.42%	97.25%

Plants that contains it

• Seriphidium szovitzianum

Cross-Links

• PubChem: 162862799
• LOTUS: LTS0238832
• wikiData: Q104914506