3-[4-Hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]propanoic acid

Details

• Internal ID: c14303e6-8f79-464c-9d72-b3d38598c49e
• Taxonomy: Phenylpropanoids and polyketides > Phenylpropanoic acids
• IUPAC Name: 3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]propanoic acid
• SMILES (Canonical): CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)CCC(=O)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)CCC(=O)O)C
• InChI: InChI=1S/C19H26O3/c1-13(2)5-8-16-11-15(7-10-18(20)21)12-17(19(16)22)9-6-14(3)4/h5-6,11-12,22H,7-10H2,1-4H3,(H,20,21)
• InChI Key: KRXZPYDOSGHFEM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.40 g/mol
• Exact Mass: 302.18819469 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.43
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5665	56.65%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.9094	90.94%
OATP2B1 inhibitior	-	0.7143	71.43%
OATP1B1 inhibitior	+	0.8290	82.90%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7163	71.63%
P-glycoprotein inhibitior	-	0.8072	80.72%
P-glycoprotein substrate	-	0.9061	90.61%
CYP3A4 substrate	-	0.6156	61.56%
CYP2C9 substrate	-	0.5641	56.41%
CYP2D6 substrate	-	0.8445	84.45%
CYP3A4 inhibition	-	0.7474	74.74%
CYP2C9 inhibition	-	0.6781	67.81%
CYP2C19 inhibition	-	0.5245	52.45%
CYP2D6 inhibition	-	0.8097	80.97%
CYP1A2 inhibition	-	0.5812	58.12%
CYP2C8 inhibition	-	0.8415	84.15%
CYP inhibitory promiscuity	-	0.6918	69.18%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7383	73.83%
Carcinogenicity (trinary)	Non-required	0.7388	73.88%
Eye corrosion	-	0.9843	98.43%
Eye irritation	+	0.8213	82.13%
Skin irritation	-	0.6167	61.67%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5913	59.13%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	+	0.6994	69.94%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8888	88.88%
Acute Oral Toxicity (c)	III	0.6990	69.90%
Estrogen receptor binding	+	0.7400	74.00%
Androgen receptor binding	+	0.5325	53.25%
Thyroid receptor binding	+	0.6124	61.24%
Glucocorticoid receptor binding	+	0.7003	70.03%
Aromatase binding	+	0.5703	57.03%
PPAR gamma	+	0.8958	89.58%
Honey bee toxicity	-	0.9559	95.59%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	+	0.9897	98.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.62%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.03%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.90%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.77%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.45%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.93%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.24%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	81.27%	90.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.17%	99.15%

Plants that contains it

• Camptotheca acuminata

Cross-Links

• PubChem: 5316551
• NPASS: NPC1294