(5Z,9E,11aR)-11a-hydroxy-3,6,10-trimethyl-8,11-dihydro-7H-cyclodeca[b]furan-2,4-dione

Details

• Internal ID: ebd9ef71-bc00-4dcb-af55-f5a9e0222cc7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (5Z,9E,11aR)-11a-hydroxy-3,6,10-trimethyl-8,11-dihydro-7H-cyclodeca[b]furan-2,4-dione
• SMILES (Canonical): CC1=CC(=O)C2=C(C(=O)OC2(CC(=CCC1)C)O)C
• SMILES (Isomeric): C/C/1=C/C(=O)C2=C(C(=O)O[C@@]2(C/C(=C/CC1)/C)O)C
• InChI: InChI=1S/C15H18O4/c1-9-5-4-6-10(2)8-15(18)13(12(16)7-9)11(3)14(17)19-15/h6-7,18H,4-5,8H2,1-3H3/b9-7-,10-6+/t15-/m1/s1
• InChI Key: YTJZWVGDRDYIMD-NBKDOUJMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 4
• 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	+	0.9844	98.44%
Caco-2	+	0.9349	93.49%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6761	67.61%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.9502	95.02%
OATP1B3 inhibitior	+	0.9538	95.38%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5836	58.36%
P-glycoprotein inhibitior	-	0.9040	90.40%
P-glycoprotein substrate	-	0.9284	92.84%
CYP3A4 substrate	+	0.5303	53.03%
CYP2C9 substrate	-	0.8140	81.40%
CYP2D6 substrate	-	0.8845	88.45%
CYP3A4 inhibition	-	0.6558	65.58%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9434	94.34%
CYP2D6 inhibition	-	0.9609	96.09%
CYP1A2 inhibition	+	0.5425	54.25%
CYP2C8 inhibition	-	0.8809	88.09%
CYP inhibitory promiscuity	-	0.9840	98.40%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5490	54.90%
Eye corrosion	-	0.9725	97.25%
Eye irritation	-	0.6110	61.10%
Skin irritation	+	0.6623	66.23%
Skin corrosion	-	0.8867	88.67%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6507	65.07%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.7158	71.58%
skin sensitisation	-	0.8106	81.06%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7149	71.49%
Acute Oral Toxicity (c)	III	0.4048	40.48%
Estrogen receptor binding	-	0.7331	73.31%
Androgen receptor binding	+	0.5490	54.90%
Thyroid receptor binding	-	0.6825	68.25%
Glucocorticoid receptor binding	-	0.6525	65.25%
Aromatase binding	-	0.6579	65.79%
PPAR gamma	+	0.5853	58.53%
Honey bee toxicity	-	0.9397	93.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9735	97.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.28%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.69%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	94.16%	89.63%
CHEMBL2581	P07339	Cathepsin D	93.73%	98.95%
CHEMBL4208	P20618	Proteasome component C5	87.04%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.76%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.14%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.64%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.80%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.82%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	81.09%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.45%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.43%	96.09%

Plants that contains it

• Curcuma aromatica

Cross-Links

• PubChem: 101492101
• LOTUS: LTS0272288
• wikiData: Q105361593