methyl 2-[(1S,3Z,5Z,7S,10R)-7-hydroxy-6,10-dimethyl-2-oxo-11-oxabicyclo[8.1.0]undeca-3,5-dien-3-yl]prop-2-enoate

Details

• Internal ID: 3618bb6c-e75a-4a88-953f-cd86037849a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Germacrane sesquiterpenoids
• IUPAC Name: methyl 2-[(1S,3Z,5Z,7S,10R)-7-hydroxy-6,10-dimethyl-2-oxo-11-oxabicyclo[8.1.0]undeca-3,5-dien-3-yl]prop-2-enoate
• SMILES (Canonical): CC1=CC=C(C(=O)C2C(O2)(CCC1O)C)C(=C)C(=O)OC
• SMILES (Isomeric): C/C/1=C/C=C(\C(=O)[C@@H]2[C@](O2)(CC[C@@H]1O)C)/C(=C)C(=O)OC
• InChI: InChI=1S/C16H20O5/c1-9-5-6-11(10(2)15(19)20-4)13(18)14-16(3,21-14)8-7-12(9)17/h5-6,12,14,17H,2,7-8H2,1,3-4H3/b9-5-,11-6-/t12-,14+,16+/m0/s1
• InChI Key: KNPCPDRRJCEGQP-ATRFMESASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.33 g/mol
• Exact Mass: 292.13107373 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.47
• 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	+	0.9731	97.31%
Caco-2	+	0.5615	56.15%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5008	50.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9286	92.86%
OATP1B3 inhibitior	+	0.9466	94.66%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7521	75.21%
BSEP inhibitior	-	0.7580	75.80%
P-glycoprotein inhibitior	-	0.8758	87.58%
P-glycoprotein substrate	-	0.8165	81.65%
CYP3A4 substrate	+	0.6316	63.16%
CYP2C9 substrate	-	0.6127	61.27%
CYP2D6 substrate	-	0.8834	88.34%
CYP3A4 inhibition	+	0.5364	53.64%
CYP2C9 inhibition	-	0.8302	83.02%
CYP2C19 inhibition	-	0.8059	80.59%
CYP2D6 inhibition	-	0.9405	94.05%
CYP1A2 inhibition	-	0.6441	64.41%
CYP2C8 inhibition	-	0.8324	83.24%
CYP inhibitory promiscuity	-	0.9831	98.31%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.8543	85.43%
Carcinogenicity (trinary)	Non-required	0.6027	60.27%
Eye corrosion	-	0.9779	97.79%
Eye irritation	-	0.8007	80.07%
Skin irritation	-	0.5615	56.15%
Skin corrosion	-	0.8961	89.61%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4456	44.56%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5944	59.44%
skin sensitisation	-	0.7261	72.61%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5971	59.71%
Acute Oral Toxicity (c)	III	0.5036	50.36%
Estrogen receptor binding	+	0.6712	67.12%
Androgen receptor binding	-	0.6212	62.12%
Thyroid receptor binding	-	0.6168	61.68%
Glucocorticoid receptor binding	+	0.5511	55.11%
Aromatase binding	+	0.6001	60.01%
PPAR gamma	+	0.5916	59.16%
Honey bee toxicity	-	0.8616	86.16%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8439	84.39%

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	95.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.10%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.24%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.34%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.54%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	84.98%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.94%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	84.01%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.49%	89.00%
CHEMBL1871	P10275	Androgen Receptor	81.67%	96.43%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.38%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.32%	95.89%

Plants that contains it

• Vernonia marginata

Cross-Links

• PubChem: 162858645
• LOTUS: LTS0186050
• wikiData: Q105143504