(1S,2S,3S,7S,9Z,11R)-2,11-dihydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.03,7]tetradec-9-en-5-one

Details

• Internal ID: ec7cc7a1-990d-4b60-a90c-7b6eb73c03fe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (1S,2S,3S,7S,9Z,11R)-2,11-dihydroxy-1-methyl-6-methylidene-4-oxatricyclo[8.3.1.03,7]tetradec-9-en-5-one
• SMILES (Canonical): CC12CCC(C(=CCC3C(C1O)OC(=O)C3=C)C2)O
• SMILES (Isomeric): C[C@@]12CC[C@H](/C(=C\C[C@@H]3[C@@H]([C@H]1O)OC(=O)C3=C)/C2)O
• InChI: InChI=1S/C15H20O4/c1-8-10-4-3-9-7-15(2,6-5-11(9)16)13(17)12(10)19-14(8)18/h3,10-13,16-17H,1,4-7H2,2H3/b9-3-/t10-,11+,12-,13+,15-/m0/s1
• InChI Key: FCGLYZCSDMGPGQ-CFSHXSAFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.33
• 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	+	0.9902	99.02%
Caco-2	+	0.6900	69.00%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7716	77.16%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.9104	91.04%
OATP1B3 inhibitior	+	0.9402	94.02%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.9769	97.69%
P-glycoprotein inhibitior	-	0.9457	94.57%
P-glycoprotein substrate	-	0.8727	87.27%
CYP3A4 substrate	+	0.5985	59.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8387	83.87%
CYP3A4 inhibition	-	0.8822	88.22%
CYP2C9 inhibition	-	0.8951	89.51%
CYP2C19 inhibition	-	0.8022	80.22%
CYP2D6 inhibition	-	0.9156	91.56%
CYP1A2 inhibition	-	0.5676	56.76%
CYP2C8 inhibition	-	0.8139	81.39%
CYP inhibitory promiscuity	-	0.9310	93.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5176	51.76%
Eye corrosion	-	0.9814	98.14%
Eye irritation	-	0.8963	89.63%
Skin irritation	+	0.5404	54.04%
Skin corrosion	-	0.8990	89.90%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4625	46.25%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6315	63.15%
skin sensitisation	-	0.7701	77.01%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.7721	77.21%
Acute Oral Toxicity (c)	IV	0.4190	41.90%
Estrogen receptor binding	+	0.5400	54.00%
Androgen receptor binding	+	0.5844	58.44%
Thyroid receptor binding	-	0.6176	61.76%
Glucocorticoid receptor binding	+	0.6584	65.84%
Aromatase binding	-	0.5199	51.99%
PPAR gamma	-	0.7207	72.07%
Honey bee toxicity	-	0.7835	78.35%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9870	98.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.85%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.24%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.64%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.11%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.88%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.04%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.51%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.23%	90.17%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.37%	93.03%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.75%	93.04%
CHEMBL2581	P07339	Cathepsin D	82.55%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.61%	86.33%

Plants that contains it

• Eriocephalus kingesii

Cross-Links

• PubChem: 162905609
• LOTUS: LTS0070513
• wikiData: Q104993141