(1S,2S,6S,11R,12R,14S)-11-hydroxy-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one

Details

• Internal ID: 0ee7d0c8-69cc-4d04-bb2f-dd08865ce9a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (1S,2S,6S,11R,12R,14S)-11-hydroxy-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one
• SMILES (Canonical): CC1=C2C(C3C(CC1)C(=C)C(=O)O3)C4(C(C2O)O4)C
• SMILES (Isomeric): CC1=C2[C@@H]([C@@H]3[C@@H](CC1)C(=C)C(=O)O3)[C@]4([C@@H]([C@@H]2O)O4)C
• InChI: InChI=1S/C15H18O4/c1-6-4-5-8-7(2)14(17)18-12(8)10-9(6)11(16)13-15(10,3)19-13/h8,10-13,16H,2,4-5H2,1,3H3/t8-,10-,11+,12-,13+,15-/m0/s1
• InChI Key: QHQLGIQQPRVTCT-BTXPOQARSA-N
• Popularity: 1 reference 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): 59.10 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.34
• 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	+	0.9660	96.60%
Caco-2	+	0.6701	67.01%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6365	63.65%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8832	88.32%
OATP1B3 inhibitior	+	0.9585	95.85%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9439	94.39%
P-glycoprotein inhibitior	-	0.8319	83.19%
P-glycoprotein substrate	-	0.8238	82.38%
CYP3A4 substrate	+	0.6036	60.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8367	83.67%
CYP3A4 inhibition	-	0.7389	73.89%
CYP2C9 inhibition	-	0.8523	85.23%
CYP2C19 inhibition	-	0.8395	83.95%
CYP2D6 inhibition	-	0.8820	88.20%
CYP1A2 inhibition	+	0.5097	50.97%
CYP2C8 inhibition	-	0.6855	68.55%
CYP inhibitory promiscuity	-	0.8860	88.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5285	52.85%
Eye corrosion	-	0.9748	97.48%
Eye irritation	-	0.7039	70.39%
Skin irritation	-	0.5491	54.91%
Skin corrosion	-	0.8480	84.80%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6304	63.04%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.7261	72.61%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5898	58.98%
Acute Oral Toxicity (c)	III	0.3370	33.70%
Estrogen receptor binding	+	0.6612	66.12%
Androgen receptor binding	+	0.6540	65.40%
Thyroid receptor binding	-	0.5386	53.86%
Glucocorticoid receptor binding	-	0.4773	47.73%
Aromatase binding	-	0.6058	60.58%
PPAR gamma	-	0.6789	67.89%
Honey bee toxicity	-	0.7780	77.80%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9571	95.71%

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	91.98%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.65%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.18%	91.11%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.81%	93.03%
CHEMBL4530	P00488	Coagulation factor XIII	86.21%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.86%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.87%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.75%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.42%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.07%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.93%	94.45%

Plants that contains it

• Kaunia lasiophthalma

Cross-Links

• PubChem: 14589134
• LOTUS: LTS0258019
• wikiData: Q105221078