(8-hydroxy-3,6,10-trimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl) 2-methylbut-2-enoate

Details

• Internal ID: da4cea59-6ddc-4d7e-8438-906149f4393d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (8-hydroxy-3,6,10-trimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl) 2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=CC(CC(=CC2C1C(C(=O)O2)C)C)O)C
• SMILES (Isomeric): CC=C(C)C(=O)OC1CC(=CC(CC(=CC2C1C(C(=O)O2)C)C)O)C
• InChI: InChI=1S/C20H28O5/c1-6-13(4)19(22)24-16-9-11(2)7-15(21)8-12(3)10-17-18(16)14(5)20(23)25-17/h6-7,10,14-18,21H,8-9H2,1-5H3
• InChI Key: ZZZSTRSHESHLMT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9815	98.15%
Caco-2	+	0.8036	80.36%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5890	58.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8711	87.11%
OATP1B3 inhibitior	+	0.9292	92.92%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7374	73.74%
P-glycoprotein inhibitior	+	0.5818	58.18%
P-glycoprotein substrate	-	0.7614	76.14%
CYP3A4 substrate	+	0.5909	59.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9014	90.14%
CYP3A4 inhibition	-	0.8218	82.18%
CYP2C9 inhibition	-	0.8790	87.90%
CYP2C19 inhibition	-	0.8653	86.53%
CYP2D6 inhibition	-	0.9559	95.59%
CYP1A2 inhibition	-	0.6769	67.69%
CYP2C8 inhibition	-	0.9160	91.60%
CYP inhibitory promiscuity	-	0.9097	90.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4907	49.07%
Eye corrosion	-	0.9648	96.48%
Eye irritation	-	0.9112	91.12%
Skin irritation	-	0.6183	61.83%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.5382	53.82%
Human Ether-a-go-go-Related Gene inhibition	+	0.8036	80.36%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6607	66.07%
skin sensitisation	-	0.7712	77.12%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7705	77.05%
Acute Oral Toxicity (c)	II	0.3684	36.84%
Estrogen receptor binding	-	0.5899	58.99%
Androgen receptor binding	-	0.5328	53.28%
Thyroid receptor binding	-	0.5328	53.28%
Glucocorticoid receptor binding	-	0.5175	51.75%
Aromatase binding	-	0.6368	63.68%
PPAR gamma	-	0.6386	63.86%
Honey bee toxicity	-	0.7022	70.22%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9326	93.26%

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	90.73%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.92%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.69%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.61%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.53%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.84%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.49%	99.23%
CHEMBL2581	P07339	Cathepsin D	84.15%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	80.63%	91.19%

Plants that contains it

• Perityle emoryi

Cross-Links

• PubChem: 163021544
• LOTUS: LTS0026270
• wikiData: Q105387227