Xerulinic acid

Details

• Internal ID: 80019d89-3754-4f47-a482-bfa592952ee9
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Long-chain fatty acids
• IUPAC Name: (2E,8E,10E,12E,14Z)-14-(5-oxofuran-2-ylidene)tetradeca-2,8,10,12-tetraen-4,6-diynoic acid
• SMILES (Canonical): C1=CC(=O)OC1=CC=CC=CC=CC#CC#CC=CC(=O)O
• SMILES (Isomeric): C\1=CC(=O)O/C1=C\C=C\C=C\C=C\C#CC#C/C=C/C(=O)O
• InChI: InChI=1S/C18H12O4/c19-17(20)13-11-9-7-5-3-1-2-4-6-8-10-12-16-14-15-18(21)22-16/h1-2,4,6,8,10-15H,(H,19,20)/b2-1+,6-4+,10-8+,13-11+,16-12-
• InChI Key: PINXAKGQRZGYOZ-LNUZTLHMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₂O₄
• Molecular Weight: 292.30 g/mol
• Exact Mass: 292.07355886 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.30
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 132971-62-1
• (2E,8E,10E,12E,14Z)-14-(5-oxofuran-2-ylidene)tetradeca-2,8,10,12-tetraen-4,6-diynoic acid
• 2,8,10,12-Tetradecatetraene-4,6-diynoic acid, 14-(5-oxo-2(5H)-furanylidene)-, (Z,E,E,E,E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9703	97.03%
Caco-2	-	0.6573	65.73%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7618	76.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8995	89.95%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8748	87.48%
P-glycoprotein inhibitior	-	0.8202	82.02%
P-glycoprotein substrate	-	0.9444	94.44%
CYP3A4 substrate	-	0.5430	54.30%
CYP2C9 substrate	+	0.5888	58.88%
CYP2D6 substrate	-	0.8797	87.97%
CYP3A4 inhibition	-	0.9359	93.59%
CYP2C9 inhibition	-	0.9126	91.26%
CYP2C19 inhibition	-	0.8884	88.84%
CYP2D6 inhibition	-	0.9519	95.19%
CYP1A2 inhibition	-	0.8250	82.50%
CYP2C8 inhibition	-	0.7624	76.24%
CYP inhibitory promiscuity	-	0.9279	92.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8113	81.13%
Carcinogenicity (trinary)	Danger	0.4115	41.15%
Eye corrosion	+	0.6791	67.91%
Eye irritation	-	0.6171	61.71%
Skin irritation	+	0.6734	67.34%
Skin corrosion	+	0.5838	58.38%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6238	62.38%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.5077	50.77%
skin sensitisation	-	0.7157	71.57%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.7214	72.14%
Acute Oral Toxicity (c)	II	0.5420	54.20%
Estrogen receptor binding	+	0.6589	65.89%
Androgen receptor binding	-	0.5761	57.61%
Thyroid receptor binding	-	0.6346	63.46%
Glucocorticoid receptor binding	-	0.5788	57.88%
Aromatase binding	+	0.7604	76.04%
PPAR gamma	+	0.8367	83.67%
Honey bee toxicity	-	0.8919	89.19%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7891	78.91%

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	87.20%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	85.16%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.26%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.26%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.95%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6439346
• LOTUS: LTS0157312
• wikiData: Q105209619