(3S,3aR,4S,6E,10E,11aR)-4-hydroxy-3,6,10-trimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: 2e4dd80c-5282-405b-9709-a4ee0fb0e950
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aR,4S,6E,10E,11aR)-4-hydroxy-3,6,10-trimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2C(CC(=CCCC(=CC2OC1=O)C)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C/C(=C/CC/C(=C/[C@H]2OC1=O)/C)/C)O
• InChI: InChI=1S/C15H22O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,11-14,16H,4,6-7H2,1-3H3/b9-5+,10-8+/t11-,12-,13+,14+/m0/s1
• InChI Key: TXSIFZZILWRCIY-VLUUFLOMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.60
• 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	+	0.9959	99.59%
Caco-2	+	0.8564	85.64%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4885	48.85%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.9317	93.17%
OATP1B3 inhibitior	+	0.9608	96.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.8239	82.39%
P-glycoprotein inhibitior	-	0.9046	90.46%
P-glycoprotein substrate	-	0.9043	90.43%
CYP3A4 substrate	+	0.5220	52.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.7212	72.12%
CYP2C9 inhibition	-	0.9414	94.14%
CYP2C19 inhibition	-	0.8785	87.85%
CYP2D6 inhibition	-	0.9592	95.92%
CYP1A2 inhibition	+	0.6076	60.76%
CYP2C8 inhibition	-	0.9424	94.24%
CYP inhibitory promiscuity	-	0.9595	95.95%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5690	56.90%
Eye corrosion	-	0.9599	95.99%
Eye irritation	-	0.8792	87.92%
Skin irritation	+	0.6182	61.82%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8197	81.97%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5426	54.26%
skin sensitisation	-	0.6924	69.24%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6264	62.64%
Acute Oral Toxicity (c)	III	0.3794	37.94%
Estrogen receptor binding	-	0.8238	82.38%
Androgen receptor binding	-	0.6615	66.15%
Thyroid receptor binding	-	0.6793	67.93%
Glucocorticoid receptor binding	-	0.6704	67.04%
Aromatase binding	-	0.8927	89.27%
PPAR gamma	-	0.7045	70.45%
Honey bee toxicity	-	0.8752	87.52%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9458	94.58%

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	92.44%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.65%	97.25%
CHEMBL2581	P07339	Cathepsin D	88.92%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.05%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.38%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.37%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.24%	86.33%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.44%	86.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.76%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	80.30%	91.49%

Plants that contains it

• Achillea atrata
• Conioselinum smithii
• Mikania pohlii
• Tanacetopsis mucronata

Cross-Links

• PubChem: 14020162
• NPASS: NPC147085
• LOTUS: LTS0204639
• wikiData: Q105266972