N-(E)-Caffeoyl-L-tyrosine

Details

• Internal ID: 7a54cc08-89b9-438b-bade-c95d6c54b2bf
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Tyrosine and derivatives
• IUPAC Name: (2S)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
• SMILES (Canonical): C1=CC(=CC=C1CC(C(=O)O)NC(=O)C=CC2=CC(=C(C=C2)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C[C@@H](C(=O)O)NC(=O)/C=C/C2=CC(=C(C=C2)O)O)O
• InChI: InChI=1S/C18H17NO6/c20-13-5-1-11(2-6-13)9-14(18(24)25)19-17(23)8-4-12-3-7-15(21)16(22)10-12/h1-8,10,14,20-22H,9H2,(H,19,23)(H,24,25)/b8-4+/t14-/m0/s1
• InChI Key: JRXLVUMFJASLDR-PXYYCUNGSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₇NO₆
• Molecular Weight: 343.30 g/mol
• Exact Mass: 343.10558726 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.63
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• Angola I
• Caffeoyl-N-tyrosine
• C6KYU23R4U
• N-(E)-Caffeoyl-L-tyrosine
• N-[3',4'-Dihydroxy-(E)-cinnamoyl]-L-tyrosine
• CHEMBL4126715
• L-Tyrosine, N-((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)-
• L-Tyrosine, N-(3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)-, (E)-
• N-((2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl)-L-tyrosine
• (2S)-2-(((E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl)amino)-3-(4-hydroxyphenyl)propanoic acid
• L-Tyrosine, N-[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-
• (2S)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-3-(4-hydroxyphenyl)propanoic Acid
• caffeoyl-tyrosine
• N-Caffeoyltyrosine
• UNII-C6KYU23R4U
• DTXSID601035777
• BDBM50272439
• N-[3-(3,4-Dihydroxyphenyl)acryloyl]-L-tyrosine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9384	93.84%
Caco-2	-	0.9389	93.89%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6035	60.35%
OATP2B1 inhibitior	-	0.5785	57.85%
OATP1B1 inhibitior	+	0.9161	91.61%
OATP1B3 inhibitior	+	0.9396	93.96%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4811	48.11%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.8630	86.30%
CYP3A4 substrate	-	0.5490	54.90%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8475	84.75%
CYP3A4 inhibition	-	0.8643	86.43%
CYP2C9 inhibition	-	0.9188	91.88%
CYP2C19 inhibition	-	0.9473	94.73%
CYP2D6 inhibition	-	0.9340	93.40%
CYP1A2 inhibition	-	0.8955	89.55%
CYP2C8 inhibition	+	0.5605	56.05%
CYP inhibitory promiscuity	-	0.9348	93.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7011	70.11%
Carcinogenicity (trinary)	Non-required	0.7195	71.95%
Eye corrosion	-	0.9963	99.63%
Eye irritation	-	0.8988	89.88%
Skin irritation	-	0.7824	78.24%
Skin corrosion	-	0.9687	96.87%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4331	43.31%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.7467	74.67%
skin sensitisation	-	0.7653	76.53%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8458	84.58%
Acute Oral Toxicity (c)	III	0.7383	73.83%
Estrogen receptor binding	-	0.5059	50.59%
Androgen receptor binding	+	0.7893	78.93%
Thyroid receptor binding	-	0.6465	64.65%
Glucocorticoid receptor binding	+	0.5747	57.47%
Aromatase binding	-	0.5926	59.26%
PPAR gamma	+	0.6268	62.68%
Honey bee toxicity	-	0.8000	80.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9644	96.44%

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	98.01%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.62%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	95.61%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.45%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	93.15%	91.49%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.92%	95.50%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	89.78%	89.33%
CHEMBL221	P23219	Cyclooxygenase-1	89.29%	90.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.00%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.50%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.85%	96.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.83%	100.00%
CHEMBL3194	P02766	Transthyretin	86.22%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.18%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.86%	91.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.69%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.37%	90.71%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	82.76%	92.29%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	82.52%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.49%	89.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.47%	97.53%
CHEMBL1907599	P05556	Integrin alpha-4/beta-1	80.15%	92.86%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.07%	93.56%

Plants that contains it

• Aconitum liangshanicum
• Aconitum sachalinense
• Ageratina gracilis
• Alstonia deplanchei
• Asteriscus graveolens
• Baccharis megapotamica
• Centrosema pascuorum
• Ceratozamia fuscoviridis
• Citrus glauca
• Coffea canephora
• Critonia quadrangularis
• Ficus simplicissima
• Flemingia macrophylla
• Gynura bicolor
• Haplophyllum dauricum
• Marrubium supinum
• Metalasia capitata
• Orthosphenia mexicana
• Oxyanthus speciosus
• Quercus dentata
• Rheum tanguticum
• Rhynchopsidium pumilum
• Senecio latifolius
• Senecio peripotamus
• Solanum elaeagnifolium
• Stevia mercedensis
• Strychnos tabascana
• Styrax hookeri
• Swinglea glutinosa
• Theobroma cacao
• Thuja standishii
• Verbesina rupestris

Cross-Links

• PubChem: 10308838
• NPASS: NPC223548
• LOTUS: LTS0216580
• wikiData: Q105134157