(3S,3aS,5R,6E,10Z,11aS)-5-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: 3bbe3632-54d4-4c06-b05c-0de12f11c670
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aS,5R,6E,10Z,11aS)-5-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2CC(C(=CCCC(=CC2OC1=O)CO)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@H](/C(=C/CC/C(=C/[C@H]2OC1=O)/CO)/C)O
• InChI: InChI=1S/C15H22O4/c1-9-4-3-5-11(8-16)6-14-12(7-13(9)17)10(2)15(18)19-14/h4,6,10,12-14,16-17H,3,5,7-8H2,1-2H3/b9-4+,11-6-/t10-,12-,13+,14+/m0/s1
• InChI Key: GSLRFQSAMMVDEI-BPWUPUDHSA-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: 0.60
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9845	98.45%
Caco-2	+	0.7482	74.82%
Blood Brain Barrier	+	0.5105	51.05%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7626	76.26%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9250	92.50%
OATP1B3 inhibitior	+	0.9676	96.76%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.5863	58.63%
BSEP inhibitior	-	0.8994	89.94%
P-glycoprotein inhibitior	-	0.9332	93.32%
P-glycoprotein substrate	-	0.7345	73.45%
CYP3A4 substrate	+	0.5459	54.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.6221	62.21%
CYP2C9 inhibition	-	0.9370	93.70%
CYP2C19 inhibition	-	0.9051	90.51%
CYP2D6 inhibition	-	0.8863	88.63%
CYP1A2 inhibition	-	0.6788	67.88%
CYP2C8 inhibition	-	0.8925	89.25%
CYP inhibitory promiscuity	-	0.8832	88.32%
UGT catelyzed	-	0.7638	76.38%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6936	69.36%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9439	94.39%
Skin irritation	-	0.6617	66.17%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.5878	58.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.7950	79.50%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8540	85.40%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6712	67.12%
Acute Oral Toxicity (c)	III	0.5285	52.85%
Estrogen receptor binding	-	0.6867	68.67%
Androgen receptor binding	-	0.7212	72.12%
Thyroid receptor binding	-	0.5261	52.61%
Glucocorticoid receptor binding	+	0.7024	70.24%
Aromatase binding	-	0.8070	80.70%
PPAR gamma	-	0.7528	75.28%
Honey bee toxicity	-	0.8969	89.69%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8943	89.43%

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	92.67%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.71%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.65%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.93%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.79%	91.11%
CHEMBL2581	P07339	Cathepsin D	86.52%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.70%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.82%	100.00%

Plants that contains it

• Centaurea aspera

Cross-Links

• PubChem: 162981776
• LOTUS: LTS0255018
• wikiData: Q105017280