3-[4-hydroxy-3-[(E)-4-hydroxy-3-methylbut-2-enyl]-5-(3-methylbut-2-enyl)phenyl]propanoic acid

Details

• Internal ID: fee004a9-c6c7-4f75-85e2-a33cc9edeba9
• Taxonomy: Phenylpropanoids and polyketides > Phenylpropanoic acids
• IUPAC Name: 3-[4-hydroxy-3-[(E)-4-hydroxy-3-methylbut-2-enyl]-5-(3-methylbut-2-enyl)phenyl]propanoic acid
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)CCC(=O)O)CC=C(C)CO)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)CCC(=O)O)C/C=C(\C)/CO)O)C
• InChI: InChI=1S/C19H26O4/c1-13(2)4-7-16-10-15(6-9-18(21)22)11-17(19(16)23)8-5-14(3)12-20/h4-5,10-11,20,23H,6-9,12H2,1-3H3,(H,21,22)/b14-5+
• InChI Key: JGRRPNPEKNCQBH-LHHJGKSTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.18310931 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.40
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.4900	49.00%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.9265	92.65%
OATP2B1 inhibitior	-	0.7119	71.19%
OATP1B1 inhibitior	+	0.8333	83.33%
OATP1B3 inhibitior	+	0.9050	90.50%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6292	62.92%
BSEP inhibitior	+	0.8053	80.53%
P-glycoprotein inhibitior	-	0.8479	84.79%
P-glycoprotein substrate	-	0.8494	84.94%
CYP3A4 substrate	-	0.5555	55.55%
CYP2C9 substrate	-	0.5827	58.27%
CYP2D6 substrate	-	0.8448	84.48%
CYP3A4 inhibition	+	0.5980	59.80%
CYP2C9 inhibition	-	0.7436	74.36%
CYP2C19 inhibition	-	0.6101	61.01%
CYP2D6 inhibition	-	0.7671	76.71%
CYP1A2 inhibition	+	0.7237	72.37%
CYP2C8 inhibition	-	0.7944	79.44%
CYP inhibitory promiscuity	-	0.7574	75.74%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.7628	76.28%
Carcinogenicity (trinary)	Non-required	0.7455	74.55%
Eye corrosion	-	0.9928	99.28%
Eye irritation	+	0.5746	57.46%
Skin irritation	-	0.7757	77.57%
Skin corrosion	-	0.9699	96.99%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5318	53.18%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.5732	57.32%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7086	70.86%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8910	89.10%
Acute Oral Toxicity (c)	III	0.5564	55.64%
Estrogen receptor binding	+	0.6505	65.05%
Androgen receptor binding	+	0.5521	55.21%
Thyroid receptor binding	+	0.5706	57.06%
Glucocorticoid receptor binding	+	0.6695	66.95%
Aromatase binding	-	0.5377	53.77%
PPAR gamma	+	0.8628	86.28%
Honey bee toxicity	-	0.9467	94.67%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	+	0.9964	99.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.80%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.18%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.77%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.62%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.34%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.14%	89.34%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.45%	99.15%
CHEMBL2216739	Q92523	Carnitine O-palmitoyltransferase 1, muscle isoform	81.18%	88.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.20%	91.19%

Plants that contains it

• Artemisia capillaris

Cross-Links

• PubChem: 5315670
• NPASS: NPC102485
• LOTUS: LTS0044290
• wikiData: Q105127661