4-[(2R)-2-hydroxy-3-methylbut-3-enyl]-6-[(E)-3-phenylprop-2-enyl]benzene-1,3-diol

Details

• Internal ID: 1b5c1f10-2cb1-4934-9739-2665506ba372
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: 4-[(2R)-2-hydroxy-3-methylbut-3-enyl]-6-[(E)-3-phenylprop-2-enyl]benzene-1,3-diol
• SMILES (Canonical): CC(=C)C(CC1=C(C=C(C(=C1)CC=CC2=CC=CC=C2)O)O)O
• SMILES (Isomeric): CC(=C)[C@@H](CC1=C(C=C(C(=C1)C/C=C/C2=CC=CC=C2)O)O)O
• InChI: InChI=1S/C20H22O3/c1-14(2)18(21)12-17-11-16(19(22)13-20(17)23)10-6-9-15-7-4-3-5-8-15/h3-9,11,13,18,21-23H,1,10,12H2,2H3/b9-6+/t18-/m1/s1
• InChI Key: UDNGLEQQTVYDNT-AHKGRUIUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₃
• Molecular Weight: 310.40 g/mol
• Exact Mass: 310.15689456 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 3.83
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	-	0.7576	75.76%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7507	75.07%
OATP2B1 inhibitior	-	0.5698	56.98%
OATP1B1 inhibitior	+	0.7984	79.84%
OATP1B3 inhibitior	+	0.9428	94.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7838	78.38%
BSEP inhibitior	+	0.7673	76.73%
P-glycoprotein inhibitior	-	0.7556	75.56%
P-glycoprotein substrate	-	0.8470	84.70%
CYP3A4 substrate	-	0.6066	60.66%
CYP2C9 substrate	-	0.8080	80.80%
CYP2D6 substrate	-	0.6684	66.84%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.5919	59.19%
CYP2C19 inhibition	+	0.7167	71.67%
CYP2D6 inhibition	-	0.8320	83.20%
CYP1A2 inhibition	+	0.5444	54.44%
CYP2C8 inhibition	-	0.6492	64.92%
CYP inhibitory promiscuity	+	0.8020	80.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7950	79.50%
Carcinogenicity (trinary)	Non-required	0.7241	72.41%
Eye corrosion	-	0.9833	98.33%
Eye irritation	-	0.6604	66.04%
Skin irritation	-	0.7019	70.19%
Skin corrosion	-	0.6590	65.90%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3682	36.82%
Micronuclear	-	0.5841	58.41%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	+	0.7038	70.38%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7137	71.37%
Acute Oral Toxicity (c)	III	0.6952	69.52%
Estrogen receptor binding	+	0.7912	79.12%
Androgen receptor binding	-	0.5206	52.06%
Thyroid receptor binding	+	0.6722	67.22%
Glucocorticoid receptor binding	+	0.8362	83.62%
Aromatase binding	+	0.8192	81.92%
PPAR gamma	+	0.9079	90.79%
Honey bee toxicity	-	0.8810	88.10%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	99.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.21%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	94.58%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.39%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.15%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.36%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.21%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.90%	91.71%
CHEMBL3401	O75469	Pregnane X receptor	89.52%	94.73%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.08%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.72%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.01%	93.99%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.97%	95.50%

Plants that contains it

• Erythrina crista-galli

Cross-Links

• PubChem: 163195329
• LOTUS: LTS0178991
• wikiData: Q105270426