p-Coumaryl alcohol

Details

• Internal ID: 152f9d42-72f7-4bec-8168-285f692919f5
• Taxonomy: Phenylpropanoids and polyketides > Cinnamyl alcohols
• IUPAC Name: 4-[(E)-3-hydroxyprop-1-enyl]phenol
• SMILES (Canonical): C1=CC(=CC=C1C=CCO)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/CO)O
• InChI: InChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
• InChI Key: PTNLHDGQWUGONS-OWOJBTEDSA-N
• Popularity: 1,683 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17 g/mol
• Exact Mass: 150.068079557 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.40
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 4-Coumaryl alcohol
• 3690-05-9
• 4-Hydroxycinnamyl alcohol
• Paracoumaryl alcohol
• 20649-40-5
• p-Coumaric alcohol
• trans-p-Coumaryl alcohol
• p-Hydroxycinnamic alcohol
• 4-[(1E)-3-hydroxyprop-1-en-1-yl]phenol
• 4-[(E)-3-hydroxyprop-1-enyl]phenol
• 3-Ohpp
• 4-(3-hydroxyprop-1-en-1-yl)phenol
• (e)-p-coumaryl alcohol
• p-Hydroxycinnamyl alcohol
• UNII-61POZ1QQ11
• 4-(3-Hydroxy-1-propen-1-yl)phenol
• 61POZ1QQ11
• 2-Propen-1-ol, 3-(p-hydroxyphenyl)-
• 4-((1E)-3-Hydroxy-1-propenyl)phenol
• Phenol, 4-((1E)-3-hydroxy-1-propenyl)-
• 2-Propen-1-ol, 3-(p-hydroxyphenyl)-, (E)-
• CHEBI:64555
• Phenol, 4-(3-hydroxy-1-propenyl)-
• (E)-4-(3-Hydroxy-1-propen-1-yl)phenol
• p-Coumarylalcohol
• Benzotetronate
• MFCD02169461
• p-Cumaric alcohol; p-Hydroxycinnamic alcohol
• (E)-4-coumaroyl alcohol
• 4-hydroxy-cinnamyl alcohol
• bmse000592
• bmse010083
• bmse010287
• COUMARYL ALCOHOL, P-
• SCHEMBL221967
• CHEMBL109034
• 3-(4-Hydroxyphenyl)-1-propane
• CHEBI:28386
• DTXSID50895024
• MCC1870
• HMS1547L14
• AMY22489
• ZINC01529484
• AKOS006278806
• 4-[(E)-3-hydroxy-1-propenyl]phenol
• MS-2010
• (E)-4-(3-Hydroxyprop-1-en-1-yl)phenol
• 4-[(1E)-3-Hydroxy-1-propenyl]phenol #
• CS-0255024
• C02646
• EN300-221926
• EN300-702603
• A937795
• Q420084
• Q27103667
• Z2235811101

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.9407	94.07%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7592	75.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8396	83.96%
OATP1B3 inhibitior	+	0.9397	93.97%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9330	93.30%
P-glycoprotein inhibitior	-	0.9859	98.59%
P-glycoprotein substrate	-	0.9833	98.33%
CYP3A4 substrate	-	0.7455	74.55%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.7243	72.43%
CYP3A4 inhibition	-	0.7580	75.80%
CYP2C9 inhibition	-	0.9123	91.23%
CYP2C19 inhibition	-	0.5599	55.99%
CYP2D6 inhibition	-	0.9589	95.89%
CYP1A2 inhibition	+	0.5532	55.32%
CYP2C8 inhibition	-	0.7516	75.16%
CYP inhibitory promiscuity	-	0.5058	50.58%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.6275	62.75%
Carcinogenicity (trinary)	Non-required	0.6728	67.28%
Eye corrosion	+	0.5204	52.04%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.7682	76.82%
Skin corrosion	-	0.6616	66.16%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8226	82.26%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5998	59.98%
skin sensitisation	+	0.9530	95.30%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	-	0.8750	87.50%
Nephrotoxicity	+	0.5235	52.35%
Acute Oral Toxicity (c)	III	0.4409	44.09%
Estrogen receptor binding	-	0.7130	71.30%
Androgen receptor binding	+	0.6663	66.63%
Thyroid receptor binding	-	0.7477	74.77%
Glucocorticoid receptor binding	-	0.6933	69.33%
Aromatase binding	-	0.6705	67.05%
PPAR gamma	-	0.5500	55.00%
Honey bee toxicity	-	0.9552	95.52%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.6459	64.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	95.65%	98.35%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.38%	91.11%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	92.32%	91.71%
CHEMBL3194	P02766	Transthyretin	85.87%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.29%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.03%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.75%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.76%	99.17%

Plants that contains it

• Alpinia galanga
• Alpinia officinarum
• Boschniakia rossica
• Capsicum annuum
• Cardiocrinum cordatum
• Pinellia ternata
• Rhodiola rosea
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum

Cross-Links

• PubChem: 5280535
• NPASS: NPC104216
• LOTUS: LTS0058896
• wikiData: Q420084