Xylarenic acid

Details

• Internal ID: 0425d57c-1433-4471-88e8-34101f02cc29
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2Z)-2-[(1S,3aR,7aS)-1-hydroxy-1,6,6-trimethyl-2,3,3a,5,7,7a-hexahydroinden-4-ylidene]propanoic acid
• SMILES (Canonical): CC(=C1CC(CC2C1CCC2(C)O)(C)C)C(=O)O
• SMILES (Isomeric): C/C(=C/1\CC(C[C@H]2[C@H]1CC[C@]2(C)O)(C)C)/C(=O)O
• InChI: InChI=1S/C15H24O3/c1-9(13(16)17)11-7-14(2,3)8-12-10(11)5-6-15(12,4)18/h10,12,18H,5-8H2,1-4H3,(H,16,17)/b11-9-/t10-,12-,15-/m0/s1
• InChI Key: FMPSNIUPCNLEGV-GJLKANHGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• (2Z)-2-[(1S,3aR,7aS)-1-hydroxy-1,6,6-trimethyl-2,3,3a,5,7,7a-hexahydroinden-4-ylidene]propanoic acid
• (2Z)-2-((1S,3aR,7aS)-1-hydroxy-1,6,6-trimethyl-2,3,3a,5,7,7a-hexahydroinden-4-ylidene)propanoic acid
• RefChem:195418
• CHEBI:214852

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.7568	75.68%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7883	78.83%
OATP2B1 inhibitior	-	0.8435	84.35%
OATP1B1 inhibitior	+	0.8840	88.40%
OATP1B3 inhibitior	+	0.8715	87.15%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.9113	91.13%
P-glycoprotein inhibitior	-	0.9432	94.32%
P-glycoprotein substrate	-	0.8407	84.07%
CYP3A4 substrate	+	0.5587	55.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9217	92.17%
CYP3A4 inhibition	-	0.9034	90.34%
CYP2C9 inhibition	-	0.8443	84.43%
CYP2C19 inhibition	-	0.8941	89.41%
CYP2D6 inhibition	-	0.9496	94.96%
CYP1A2 inhibition	-	0.8536	85.36%
CYP2C8 inhibition	-	0.7967	79.67%
CYP inhibitory promiscuity	-	0.9194	91.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5610	56.10%
Eye corrosion	-	0.9900	99.00%
Eye irritation	+	0.6719	67.19%
Skin irritation	+	0.6725	67.25%
Skin corrosion	-	0.9643	96.43%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4288	42.88%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6440	64.40%
skin sensitisation	+	0.6089	60.89%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5433	54.33%
Acute Oral Toxicity (c)	III	0.6192	61.92%
Estrogen receptor binding	-	0.7484	74.84%
Androgen receptor binding	+	0.5465	54.65%
Thyroid receptor binding	+	0.5375	53.75%
Glucocorticoid receptor binding	-	0.4888	48.88%
Aromatase binding	-	0.7813	78.13%
PPAR gamma	-	0.7189	71.89%
Honey bee toxicity	-	0.9634	96.34%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.32%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.76%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.40%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.11%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.43%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.29%	95.89%
CHEMBL2581	P07339	Cathepsin D	82.69%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.46%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	81.89%	95.93%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.66%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 24787195
• LOTUS: LTS0173371
• wikiData: Q77497446