(1S,2R,12S,14R)-5,9,14-trimethyl-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradeca-5,9-dien-4-one

Details

• Internal ID: 2c543e01-3cb1-4559-a74c-afe060d91c30
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (1S,2R,12S,14R)-5,9,14-trimethyl-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradeca-5,9-dien-4-one
• SMILES (Canonical): CC1=C2CC3C(C2C4C(=C(C(=O)O4)C)CC1)(O3)C
• SMILES (Isomeric): CC1=C2C[C@H]3[C@@]([C@@H]2[C@@H]4C(=C(C(=O)O4)C)CC1)(O3)C
• InChI: InChI=1S/C15H18O3/c1-7-4-5-9-8(2)14(16)17-13(9)12-10(7)6-11-15(12,3)18-11/h11-13H,4-6H2,1-3H3/t11-,12-,13-,15-/m0/s1
• InChI Key: UHDFWCWSGUBZKZ-ABHRYQDASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.8809	88.09%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6518	65.18%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9152	91.52%
OATP1B3 inhibitior	+	0.9829	98.29%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.8383	83.83%
P-glycoprotein inhibitior	-	0.7974	79.74%
P-glycoprotein substrate	-	0.8674	86.74%
CYP3A4 substrate	+	0.5632	56.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.8796	87.96%
CYP2C9 inhibition	-	0.8815	88.15%
CYP2C19 inhibition	-	0.8667	86.67%
CYP2D6 inhibition	-	0.9409	94.09%
CYP1A2 inhibition	+	0.6871	68.71%
CYP2C8 inhibition	-	0.9015	90.15%
CYP inhibitory promiscuity	-	0.9227	92.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5606	56.06%
Eye corrosion	-	0.9821	98.21%
Eye irritation	-	0.5170	51.70%
Skin irritation	-	0.5111	51.11%
Skin corrosion	-	0.8800	88.00%
Ames mutagenesis	-	0.5037	50.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5696	56.96%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6543	65.43%
skin sensitisation	-	0.6701	67.01%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6449	64.49%
Acute Oral Toxicity (c)	III	0.4064	40.64%
Estrogen receptor binding	-	0.4898	48.98%
Androgen receptor binding	+	0.5564	55.64%
Thyroid receptor binding	-	0.5563	55.63%
Glucocorticoid receptor binding	-	0.4741	47.41%
Aromatase binding	-	0.7484	74.84%
PPAR gamma	+	0.5200	52.00%
Honey bee toxicity	-	0.8153	81.53%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9745	97.45%

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	91.74%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.82%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.63%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.84%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.94%	93.40%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.22%	93.99%
CHEMBL2581	P07339	Cathepsin D	82.94%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.93%	97.09%

Plants that contains it

• Valeriana officinalis

Cross-Links

• PubChem: 11770726
• LOTUS: LTS0118915
• wikiData: Q105280103