Caffeyl alcohol

Details

• Internal ID: 30cd1578-f047-4f34-9787-e6663b766e3b
• Taxonomy: Phenylpropanoids and polyketides > Cinnamyl alcohols
• IUPAC Name: 4-[(E)-3-hydroxyprop-1-enyl]benzene-1,2-diol
• SMILES (Canonical): C1=CC(=C(C=C1C=CCO)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/CO)O)O
• InChI: InChI=1S/C9H10O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h1-4,6,10-12H,5H2/b2-1+
• InChI Key: ZCKDCRKBURQZPT-OWOJBTEDSA-N
• Popularity: 46 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17 g/mol
• Exact Mass: 166.062994177 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 3,4-Dihydroxycinnamyl alcohol
• 3598-26-3
• Caffeoyl alcohol
• 4-(3-hydroxyprop-1-en-1-yl)benzene-1,2-diol
• (E)-caffeyl alcohol
• Spectrum5_000634
• NSC624003
• 272785-02-1
• 4-[(E)-3-hydroxyprop-1-enyl]benzene-1,2-diol
• NSC-624003
• P5Y9E2Q5EQ
• CHEBI:31334
• 3-(3,4-Dihydroxyphenyl)prop-2-en-1-ol
• 2-Propen-1-ol, 3-(3,4-dihydroxyphenyl)-
• 1,2-Benzenediol, 4-(3-hydroxy-1-propenyl)-
• 4-(3-hydroxy-1-propen-1-yl)-1,2-benzenediol
• 1,2-Benzenediol, 4-(3-hydroxy-1-propen-1-yl)-
• 1,2-Benzenediol, 4-((1E)-3-hydroxy-1-propen-1-yl)-
• AC1NQZH2
• caffeicalcohol
• caffeic alcohol
• trans-Caffeoyl alcohol
• SureCN197852
• UNII-P5Y9E2Q5EQ
• SCHEMBL197852
• SPECTRUM1503992
• CHEMBL1321891
• CHEBI:86071
• DTXSID801027142
• CCG-38897
• SDCCGMLS-0066824.P001
• NCGC00095751-01
• 4-(3-Hydroxy-1-propenyl)-1,2-benzenediol
• EN300-1246637
• SR-05000002396
• SR-05000002396-1
• 4-[(1E)-3-Hydroxy-1-propen-1-yl]-1,2-benzenediol
• 4-[(1E)-3-hydroxyprop-1-en-1-yl]benzene-1,2-diol
• Q15410859

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	+	0.6450	64.50%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7940	79.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9372	93.72%
OATP1B3 inhibitior	+	0.9662	96.62%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9395	93.95%
P-glycoprotein inhibitior	-	0.9880	98.80%
P-glycoprotein substrate	-	0.9895	98.95%
CYP3A4 substrate	-	0.7552	75.52%
CYP2C9 substrate	-	0.5973	59.73%
CYP2D6 substrate	-	0.7461	74.61%
CYP3A4 inhibition	-	0.7944	79.44%
CYP2C9 inhibition	-	0.8600	86.00%
CYP2C19 inhibition	-	0.8171	81.71%
CYP2D6 inhibition	-	0.9436	94.36%
CYP1A2 inhibition	-	0.5491	54.91%
CYP2C8 inhibition	-	0.8587	85.87%
CYP inhibitory promiscuity	-	0.5815	58.15%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.7630	76.30%
Carcinogenicity (trinary)	Non-required	0.6000	60.00%
Eye corrosion	-	0.6889	68.89%
Eye irritation	+	0.9962	99.62%
Skin irritation	+	0.7306	73.06%
Skin corrosion	-	0.5358	53.58%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8644	86.44%
Micronuclear	-	0.5219	52.19%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	+	0.9596	95.96%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.7303	73.03%
Acute Oral Toxicity (c)	III	0.6783	67.83%
Estrogen receptor binding	-	0.6398	63.98%
Androgen receptor binding	+	0.7411	74.11%
Thyroid receptor binding	-	0.5494	54.94%
Glucocorticoid receptor binding	-	0.6175	61.75%
Aromatase binding	-	0.7800	78.00%
PPAR gamma	+	0.5780	57.80%
Honey bee toxicity	-	0.9412	94.12%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8623	86.23%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	39810.7 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.88%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.69%	91.49%
CHEMBL3194	P02766	Transthyretin	90.58%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.83%	91.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.81%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.29%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.05%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.50%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.87%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.03%	80.78%
CHEMBL4208	P20618	Proteasome component C5	81.24%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.99%	99.17%

Plants that contains it

• Arabidopsis thaliana
• Pinellia ternata

Cross-Links

• PubChem: 5282096
• NPASS: NPC131587
• ChEMBL: CHEMBL1321891
• LOTUS: LTS0260790
• wikiData: Q15410859