4-Hydroxy-3,5-diprenylcinnamic acid

Details

• Internal ID: fc2b2b25-98a2-4806-90a1-df3d4ea90c2b
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acids
• IUPAC Name: 3-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
• SMILES (Canonical): CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)C=CC(=O)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)C=CC(=O)O)C
• InChI: InChI=1S/C19H24O3/c1-13(2)5-8-16-11-15(7-10-18(20)21)12-17(19(16)22)9-6-14(3)4/h5-7,10-12,22H,8-9H2,1-4H3,(H,20,21)
• InChI Key: KABCFARPAMSXCC-UHFFFAOYSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₃
• Molecular Weight: 300.40 g/mol
• Exact Mass: 300.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.51
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• NCI60_040915

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.6112	61.12%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.9074	90.74%
OATP2B1 inhibitior	-	0.5699	56.99%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8010	80.10%
P-glycoprotein inhibitior	-	0.8063	80.63%
P-glycoprotein substrate	-	0.9302	93.02%
CYP3A4 substrate	-	0.6573	65.73%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	-	0.8717	87.17%
CYP3A4 inhibition	-	0.7815	78.15%
CYP2C9 inhibition	+	0.6382	63.82%
CYP2C19 inhibition	+	0.6796	67.96%
CYP2D6 inhibition	-	0.8239	82.39%
CYP1A2 inhibition	-	0.5924	59.24%
CYP2C8 inhibition	-	0.8314	83.14%
CYP inhibitory promiscuity	+	0.5659	56.59%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.6845	68.45%
Carcinogenicity (trinary)	Non-required	0.7523	75.23%
Eye corrosion	-	0.9584	95.84%
Eye irritation	+	0.9179	91.79%
Skin irritation	-	0.5540	55.40%
Skin corrosion	-	0.8980	89.80%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6533	65.33%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6666	66.66%
skin sensitisation	+	0.7285	72.85%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6696	66.96%
Acute Oral Toxicity (c)	III	0.7528	75.28%
Estrogen receptor binding	+	0.8190	81.90%
Androgen receptor binding	+	0.7378	73.78%
Thyroid receptor binding	+	0.6009	60.09%
Glucocorticoid receptor binding	+	0.8081	80.81%
Aromatase binding	+	0.6749	67.49%
PPAR gamma	+	0.8994	89.94%
Honey bee toxicity	-	0.9511	95.11%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	680 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.66%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.66%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.98%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	90.80%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	90.36%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	90.18%	91.49%
CHEMBL2581	P07339	Cathepsin D	89.27%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.96%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.29%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.65%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.83%	89.34%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.10%	89.00%

Plants that contains it

• Artemisia capillaris
• Artemisia palustris
• Baccharis polyphylla

Cross-Links

• PubChem: 126315
• LOTUS: LTS0206414
• wikiData: Q105137761