(3S,3aS,5S,11R,11aS)-5,11-dihydroxy-3-methyl-6,10-dimethylidene-3,3a,4,5,8,9,11,11a-octahydrocyclodeca[b]furan-2,7-dione

Details

• Internal ID: 3a550801-bd40-42c0-8e55-f6b9bfdb91cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3S,3aS,5S,11R,11aS)-5,11-dihydroxy-3-methyl-6,10-dimethylidene-3,3a,4,5,8,9,11,11a-octahydrocyclodeca[b]furan-2,7-dione
• SMILES (Canonical): CC1C2CC(C(=C)C(=O)CCC(=C)C(C2OC1=O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@@H](C(=C)C(=O)CCC(=C)[C@H]([C@H]2OC1=O)O)O
• InChI: InChI=1S/C15H20O5/c1-7-4-5-11(16)9(3)12(17)6-10-8(2)15(19)20-14(10)13(7)18/h8,10,12-14,17-18H,1,3-6H2,2H3/t8-,10-,12-,13+,14-/m0/s1
• InChI Key: SXXJNIDYZSKXDI-KRZNOGTGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 5
• 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	+	0.9681	96.81%
Caco-2	-	0.5449	54.49%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7099	70.99%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.9085	90.85%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8321	83.21%
BSEP inhibitior	-	0.9764	97.64%
P-glycoprotein inhibitior	-	0.9194	91.94%
P-glycoprotein substrate	-	0.8411	84.11%
CYP3A4 substrate	+	0.5165	51.65%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.9527	95.27%
CYP2C9 inhibition	-	0.8981	89.81%
CYP2C19 inhibition	-	0.8602	86.02%
CYP2D6 inhibition	-	0.9237	92.37%
CYP1A2 inhibition	-	0.6856	68.56%
CYP2C8 inhibition	-	0.9206	92.06%
CYP inhibitory promiscuity	-	0.9741	97.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5750	57.50%
Eye corrosion	-	0.9530	95.30%
Eye irritation	-	0.5778	57.78%
Skin irritation	-	0.5814	58.14%
Skin corrosion	-	0.8585	85.85%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7949	79.49%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.7677	76.77%
skin sensitisation	-	0.8189	81.89%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5692	56.92%
Acute Oral Toxicity (c)	IV	0.3634	36.34%
Estrogen receptor binding	+	0.6518	65.18%
Androgen receptor binding	-	0.6351	63.51%
Thyroid receptor binding	-	0.5635	56.35%
Glucocorticoid receptor binding	+	0.6665	66.65%
Aromatase binding	-	0.7443	74.43%
PPAR gamma	-	0.7155	71.55%
Honey bee toxicity	-	0.7606	76.06%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9129	91.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.06%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.00%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.42%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.91%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.77%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.69%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.88%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.76%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.64%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	81.57%	91.49%

Plants that contains it

• Artemisia herba-alba

Cross-Links

• PubChem: 14705667
• LOTUS: LTS0028968
• wikiData: Q105263392