(2E)-2-[(1S,2S,4R,6S,7S)-7-hydroxy-1,5,5-trimethyl-9-oxo-10-oxatricyclo[4.4.0.02,4]decan-8-ylidene]propanoic acid

Details

• Internal ID: 7b76bf17-049c-4e70-b2cc-3842fcdd1033
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (2E)-2-[(1S,2S,4R,6S,7S)-7-hydroxy-1,5,5-trimethyl-9-oxo-10-oxatricyclo[4.4.0.02,4]decan-8-ylidene]propanoic acid
• SMILES (Canonical): CC(=C1C(C2C(C3CC3C2(OC1=O)C)(C)C)O)C(=O)O
• SMILES (Isomeric): C/C(=C\1/[C@H]([C@H]2[C@]([C@H]3C[C@H]3C2(C)C)(OC1=O)C)O)/C(=O)O
• InChI: InChI=1S/C15H20O5/c1-6(12(17)18)9-10(16)11-14(2,3)7-5-8(7)15(11,4)20-13(9)19/h7-8,10-11,16H,5H2,1-4H3,(H,17,18)/b9-6+/t7-,8+,10-,11-,15+/m1/s1
• InChI Key: BJMXIQDWPYIHIE-XDHOZZIBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9853	98.53%
Caco-2	-	0.7848	78.48%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6918	69.18%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.8983	89.83%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9098	90.98%
P-glycoprotein inhibitior	-	0.8633	86.33%
P-glycoprotein substrate	-	0.8557	85.57%
CYP3A4 substrate	+	0.5677	56.77%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.9061	90.61%
CYP3A4 inhibition	-	0.9059	90.59%
CYP2C9 inhibition	-	0.8292	82.92%
CYP2C19 inhibition	-	0.8630	86.30%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	-	0.8037	80.37%
CYP2C8 inhibition	-	0.8929	89.29%
CYP inhibitory promiscuity	-	0.7313	73.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9713	97.13%
Carcinogenicity (trinary)	Non-required	0.4379	43.79%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.6991	69.91%
Skin irritation	+	0.5459	54.59%
Skin corrosion	-	0.8999	89.99%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6704	67.04%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.6461	64.61%
skin sensitisation	-	0.6267	62.67%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5776	57.76%
Acute Oral Toxicity (c)	III	0.4188	41.88%
Estrogen receptor binding	+	0.8153	81.53%
Androgen receptor binding	+	0.5662	56.62%
Thyroid receptor binding	+	0.5866	58.66%
Glucocorticoid receptor binding	+	0.6556	65.56%
Aromatase binding	-	0.5181	51.81%
PPAR gamma	+	0.6364	63.64%
Honey bee toxicity	-	0.8386	83.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9734	97.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.28%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.55%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.96%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.25%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	84.44%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.14%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.29%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.03%	89.00%

Plants that contains it

• Lindera aggregata

Cross-Links

• PubChem: 162847812
• LOTUS: LTS0113812
• wikiData: Q104937179