(1S,2R,5S,9S,10S,11S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,13-trioxatetracyclo[9.2.2.01,10.05,9]pentadec-14-en-7-one

Details

• Internal ID: 38cfdab2-2ef4-451c-81ad-6410975683d9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (1S,2R,5S,9S,10S,11S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,13-trioxatetracyclo[9.2.2.01,10.05,9]pentadec-14-en-7-one
• SMILES (Canonical): CC1(CCC2C(C3C14C=CC3(OO4)C)OC(=O)C2=C)O
• SMILES (Isomeric): C[C@]1(CC[C@@H]2[C@@H]([C@@H]3[C@@]14C=C[C@@]3(OO4)C)OC(=O)C2=C)O
• InChI: InChI=1S/C15H18O5/c1-8-9-4-5-14(3,17)15-7-6-13(2,19-20-15)11(15)10(9)18-12(8)16/h6-7,9-11,17H,1,4-5H2,2-3H3/t9-,10-,11-,13-,14+,15-/m0/s1
• InChI Key: ZTOKBJPHHAIUKE-ABVBFRSVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.27
• H-Bond Acceptor: 5
• 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	+	0.9818	98.18%
Caco-2	+	0.6221	62.21%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5986	59.86%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8441	84.41%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9678	96.78%
P-glycoprotein inhibitior	-	0.8784	87.84%
P-glycoprotein substrate	-	0.8558	85.58%
CYP3A4 substrate	+	0.6040	60.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8458	84.58%
CYP3A4 inhibition	-	0.6448	64.48%
CYP2C9 inhibition	-	0.8987	89.87%
CYP2C19 inhibition	-	0.8704	87.04%
CYP2D6 inhibition	-	0.9126	91.26%
CYP1A2 inhibition	-	0.6669	66.69%
CYP2C8 inhibition	-	0.6606	66.06%
CYP inhibitory promiscuity	-	0.9669	96.69%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5421	54.21%
Eye corrosion	-	0.9765	97.65%
Eye irritation	-	0.9542	95.42%
Skin irritation	-	0.5697	56.97%
Skin corrosion	-	0.8182	81.82%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.7754	77.54%
skin sensitisation	-	0.7383	73.83%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5678	56.78%
Acute Oral Toxicity (c)	III	0.3724	37.24%
Estrogen receptor binding	+	0.8015	80.15%
Androgen receptor binding	+	0.6818	68.18%
Thyroid receptor binding	+	0.6767	67.67%
Glucocorticoid receptor binding	+	0.6107	61.07%
Aromatase binding	+	0.5343	53.43%
PPAR gamma	+	0.7048	70.48%
Honey bee toxicity	-	0.8776	87.76%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.29%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.47%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.38%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.78%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.56%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.26%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.50%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.70%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.05%	97.79%
CHEMBL2581	P07339	Cathepsin D	81.24%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.08%	95.89%

Plants that contains it

• Artemisia frigida
• Artemisia ludoviciana
• Tanacetum parthenium

Cross-Links

• PubChem: 14219461
• LOTUS: LTS0088848
• wikiData: Q104396812