p-Coumaraldehyde

Details

• Internal ID: a5992884-fada-4f2a-b8d2-0c80380b4330
• Taxonomy: Phenylpropanoids and polyketides > Cinnamaldehydes
• IUPAC Name: (E)-3-(4-hydroxyphenyl)prop-2-enal
• SMILES (Canonical): C1=CC(=CC=C1C=CC=O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C=O)O
• InChI: InChI=1S/C9H8O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-7,11H/b2-1+
• InChI Key: CJXMVKYNVIGQBS-OWOJBTEDSA-N
• Popularity: 150 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16 g/mol
• Exact Mass: 148.052429494 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.60
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• p-Coumaraldehyde
• 2538-87-6
• 20711-53-9
• (E)-3-(4-Hydroxyphenyl)acrylaldehyde
• p-Hydroxycinnamaldehyde
• 4-hydroxycinnamaldehyde
• (E)-3-(4-hydroxyphenyl)prop-2-enal
• 4-Hydroxycinnamyl aldehyde
• trans-p-Hydroxycinnamaldehyde
• p-coumaryl aldehyde
• COUMARALDEHYDE
• 2-propenal, 3-(4-hydroxyphenyl)-, (2E)-
• (2E)-3-(4-hydroxyphenyl)acrylaldehyde
• (2E)-3-(4-hydroxyphenyl)prop-2-enal
• CHEBI:28353
• (E)-3-(4-hydroxyphenyl)-2-propenal
• 4-coumaraldehyde
• trans-p-Coumaraldehyde
• (E)-4-coumaraldehyde
• 4-hydroxy cinnamaldehyde
• bmse000611
• bmse010084
• trans-4-hydroxycinnamaldehyde
• SPECTRUM231070
• SCHEMBL196960
• SCHEMBL197453
• CHEMBL431836
• AMY5023
• MCC6940
• DTXSID001314202
• CCG-39470
• MFCD00599378
• AKOS006271961
• CS-T-13396
• NCGC00095729-01
• AS-50095
• CS-0188261
• C05608
• O10873
• A817838
• J-510715
• Q27103652
• InChI=1/C9H8O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-7,11H/b2-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9226	92.26%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7532	75.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8834	88.34%
OATP1B3 inhibitior	+	0.9630	96.30%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9030	90.30%
P-glycoprotein inhibitior	-	0.9894	98.94%
P-glycoprotein substrate	-	0.9835	98.35%
CYP3A4 substrate	-	0.7177	71.77%
CYP2C9 substrate	-	0.5954	59.54%
CYP2D6 substrate	-	0.8052	80.52%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9701	97.01%
CYP2C19 inhibition	-	0.7885	78.85%
CYP2D6 inhibition	-	0.9622	96.22%
CYP1A2 inhibition	-	0.6767	67.67%
CYP2C8 inhibition	-	0.8028	80.28%
CYP inhibitory promiscuity	-	0.8268	82.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.5821	58.21%
Carcinogenicity (trinary)	Non-required	0.6180	61.80%
Eye corrosion	+	0.9513	95.13%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.9560	95.60%
Skin corrosion	-	0.6988	69.88%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8068	80.68%
Micronuclear	-	0.5060	50.60%
Hepatotoxicity	-	0.5437	54.37%
skin sensitisation	+	0.9763	97.63%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.9375	93.75%
Nephrotoxicity	+	0.5190	51.90%
Acute Oral Toxicity (c)	III	0.7452	74.52%
Estrogen receptor binding	-	0.6814	68.14%
Androgen receptor binding	+	0.6664	66.64%
Thyroid receptor binding	-	0.7815	78.15%
Glucocorticoid receptor binding	-	0.6868	68.68%
Aromatase binding	-	0.6145	61.45%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9397	93.97%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8408	84.08%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	3548.1 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	7079.5 nM; 7079.5 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.93%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.45%	91.11%
CHEMBL3194	P02766	Transthyretin	89.89%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	88.75%	98.35%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.45%	91.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.17%	96.00%
CHEMBL4208	P20618	Proteasome component C5	80.44%	90.00%

Plants that contains it

• Ajania fruticulosa
• Alpinia galanga
• Annona glabra
• Aralia bipinnata
• Astragalus curvicarpus
• Broussonetia papyrifera
• Canarium schweinfurthii
• Carya cathayensis
• Chamaecyparis formosensis
• Cucurbita maxima
• Eucalyptus radiata
• Ginkgo biloba
• Ilex taubertiana
• Sarcophyte sanguinea
• Sonchus oleraceus
• Spiraea formosana
• Torreya grandis
• Zanthoxylum ailanthoides

Cross-Links

• PubChem: 641301
• NPASS: NPC286006
• ChEMBL: CHEMBL431836
• LOTUS: LTS0221678
• wikiData: Q27103652