3,4-Dihydroxyphenyl caffeate

Details

• Internal ID: f29e6d94-9704-4f8e-b39b-36404e6c0db2
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (3,4-dihydroxyphenyl) (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OC2=CC(=C(C=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)OC2=CC(=C(C=C2)O)O)O)O
• InChI: InChI=1S/C15H12O6/c16-11-4-1-9(7-13(11)18)2-6-15(20)21-10-3-5-12(17)14(19)8-10/h1-8,16-19H/b6-2+
• InChI Key: NIYQPBJUTVQCLM-QHHAFSJGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	+	0.5416	54.16%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7869	78.69%
OATP2B1 inhibitior	-	0.5697	56.97%
OATP1B1 inhibitior	+	0.9700	97.00%
OATP1B3 inhibitior	+	0.9643	96.43%
MATE1 inhibitior	+	0.6200	62.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6816	68.16%
P-glycoprotein inhibitior	-	0.9210	92.10%
P-glycoprotein substrate	-	0.9895	98.95%
CYP3A4 substrate	-	0.6158	61.58%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8590	85.90%
CYP3A4 inhibition	-	0.8509	85.09%
CYP2C9 inhibition	-	0.7505	75.05%
CYP2C19 inhibition	-	0.8344	83.44%
CYP2D6 inhibition	-	0.9576	95.76%
CYP1A2 inhibition	-	0.5205	52.05%
CYP2C8 inhibition	+	0.5121	51.21%
CYP inhibitory promiscuity	-	0.6316	63.16%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.7866	78.66%
Carcinogenicity (trinary)	Non-required	0.5465	54.65%
Eye corrosion	-	0.9835	98.35%
Eye irritation	+	0.9809	98.09%
Skin irritation	+	0.5120	51.20%
Skin corrosion	-	0.9642	96.42%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6992	69.92%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.5529	55.29%
skin sensitisation	+	0.7130	71.30%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.5643	56.43%
Acute Oral Toxicity (c)	III	0.7197	71.97%
Estrogen receptor binding	+	0.9206	92.06%
Androgen receptor binding	+	0.8151	81.51%
Thyroid receptor binding	+	0.7145	71.45%
Glucocorticoid receptor binding	+	0.8567	85.67%
Aromatase binding	+	0.7931	79.31%
PPAR gamma	+	0.8137	81.37%
Honey bee toxicity	-	0.7106	71.06%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9958	99.58%

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	99.10%	91.11%
CHEMBL3194	P02766	Transthyretin	95.66%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	94.24%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.52%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	92.04%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.85%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.33%	99.15%
CHEMBL4208	P20618	Proteasome component C5	90.85%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.23%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.75%	96.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.33%	80.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.29%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.65%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.72%	91.07%

Plants that contains it

• Froelichia floridana

Cross-Links

• PubChem: 102519768
• LOTUS: LTS0098263
• wikiData: Q105180033