Vinyl caffeate

Details

• Internal ID: b39491e6-07d1-4010-9206-73c295ddf92c
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: ethenyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C=COC(=O)C=CC1=CC(=C(C=C1)O)O
• SMILES (Isomeric): C=COC(=O)/C=C/C1=CC(=C(C=C1)O)O
• InChI: InChI=1S/C11H10O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h2-7,12-13H,1H2/b6-4+
• InChI Key: XVCVDNKCUNGTRP-GQCTYLIASA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.19 g/mol
• Exact Mass: 206.05790880 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• Ethenyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 179694-77-0
• 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethenyl ester, (2E)- (9CI)
• caffeic acid vinyl ester
• CHEBI:174026
• 3-(3,4-Dihydroxyphenyl)propenoic acid vinyl ester
• ethenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9671	96.71%
Caco-2	+	0.5562	55.62%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8114	81.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9666	96.66%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	+	0.6200	62.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7734	77.34%
P-glycoprotein inhibitior	-	0.9740	97.40%
P-glycoprotein substrate	-	0.9809	98.09%
CYP3A4 substrate	-	0.6148	61.48%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8578	85.78%
CYP3A4 inhibition	-	0.8226	82.26%
CYP2C9 inhibition	-	0.8684	86.84%
CYP2C19 inhibition	-	0.8466	84.66%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	-	0.8474	84.74%
CYP2C8 inhibition	-	0.5977	59.77%
CYP inhibitory promiscuity	-	0.8788	87.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7906	79.06%
Carcinogenicity (trinary)	Non-required	0.5818	58.18%
Eye corrosion	-	0.7206	72.06%
Eye irritation	+	0.9929	99.29%
Skin irritation	+	0.7180	71.80%
Skin corrosion	-	0.8322	83.22%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8458	84.58%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.5029	50.29%
skin sensitisation	+	0.7855	78.55%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.7512	75.12%
Acute Oral Toxicity (c)	III	0.5679	56.79%
Estrogen receptor binding	+	0.6957	69.57%
Androgen receptor binding	+	0.7659	76.59%
Thyroid receptor binding	-	0.5190	51.90%
Glucocorticoid receptor binding	-	0.5811	58.11%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6316	63.16%
Honey bee toxicity	-	0.8256	82.56%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9923	99.23%

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	98.82%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.66%	91.49%
CHEMBL3194	P02766	Transthyretin	94.30%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.00%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.09%	95.56%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.06%	80.78%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.89%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.72%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.75%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.60%	90.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.47%	96.12%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.95%	99.17%

Plants that contains it

• Aconitum leucostomum
• Aiouea montana
• Aquilegia ecalcarata
• Artemisia szowitziana
• Blumea axillaris
• Ceanothus velutinus
• Chlorophytum borivilianum
• Dipterocarpus dyeri
• Fragaria vesca
• Gamblea innovans
• Garcinia scortechinii
• Gardenia tubifera
• Ipomoea cairica
• Isodon lophanthoides
• Kopsia grandifolia
• Lasianthus fordii
• Ledebouria socialis
• Lycopus europaeus
• Orthosiphon aristatus var. aristatus
• Perilla frutescens
• Persea barbujana

Cross-Links

• PubChem: 11127419
• NPASS: NPC311517
• LOTUS: LTS0192219
• wikiData: Q76416688