NAV

N-Caffeoyltyramine

Identification

Generic Name
N-Caffeoyltyramine
DrugBank Accession Number
DB08754
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 299.3212
Monoisotopic: 299.115758037
Chemical Formula
C17H17NO4
Synonyms
  • N-Caffeoyltyramine
  • N-trans-Caffeoyltyramine
  • trans-N-Caffeoyltyramine
  • Typheramide
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeptide deformylaseNot AvailableHelicobacter pylori
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. These are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamic acids and derivatives
Sub Class
Hydroxycinnamic acids and derivatives
Direct Parent
Hydroxycinnamic acids and derivatives
Alternative Parents
Cinnamic acid amides / Styrenes / Catechols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Secondary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Catechol / Cinnamic acid amide / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
3LZ974DQ9J
CAS number
103188-48-3
InChI Key
VSHUQLRHTJOKTA-XBXARRHUSA-N
InChI
InChI=1S/C17H17NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-8,11,19-21H,9-10H2,(H,18,22)/b8-4+
IUPAC Name
(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
SMILES
OC1=CC=C(CCNC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1

References

General References
Not Available
Human Metabolome Database
HMDB0033026
PubChem Compound
9994897
PubChem Substance
99445225
ChemSpider
8170478
ChEMBL
CHEMBL206646
ZINC
ZINC000013515185
PDBe Ligand
Y13
PDB Entries
2ew6

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.038 mg/mLALOGPS
logP2.26ALOGPS
logP2.66Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.04Chemaxon
pKa (Strongest Basic)-0.39Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area89.79 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity85.09 m3·mol-1Chemaxon
Polarizability32.1 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9818
Blood Brain Barrier+0.6437
Caco-2 permeable-0.5411
P-glycoprotein substrateSubstrate0.5259
P-glycoprotein inhibitor INon-inhibitor0.9132
P-glycoprotein inhibitor IINon-inhibitor0.8601
Renal organic cation transporterNon-inhibitor0.804
CYP450 2C9 substrateNon-substrate0.7438
CYP450 2D6 substrateNon-substrate0.7256
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.6515
CYP450 2C9 inhibitorNon-inhibitor0.8494
CYP450 2D6 inhibitorNon-inhibitor0.8184
CYP450 2C19 inhibitorNon-inhibitor0.8622
CYP450 3A4 inhibitorNon-inhibitor0.5802
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8358
Ames testNon AMES toxic0.5123
CarcinogenicityNon-carcinogens0.9176
BiodegradationNot ready biodegradable0.5792
Rat acute toxicity1.9665 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9681
hERG inhibition (predictor II)Non-inhibitor0.6
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03di-0910000000-1c173cf7b0466780ad35
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0829000000-eb7d35ce36f098116200
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-1960000000-f5afb248262641287dcb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0v4i-0931000000-a878d0bb915876886f50
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-3910000000-893478ceb9474e187f63
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-2910000000-f595a64b264f59aa2ae5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ku-1930000000-1e4f52fe5b397d1bb7b8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-171.5914376
predicted
DarkChem Lite v0.1.0
[M-H]-172.0027376
predicted
DarkChem Lite v0.1.0
[M-H]-169.02132
predicted
DeepCCS 1.0 (2019)
[M+H]+171.6640376
predicted
DarkChem Lite v0.1.0
[M+H]+171.5607376
predicted
DarkChem Lite v0.1.0
[M+H]+171.37932
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.5137376
predicted
DarkChem Lite v0.1.0
[M+Na]+171.4897376
predicted
DarkChem Lite v0.1.0
[M+Na]+179.21092
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peptide deformylase
Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
Q672W7
Uniprot Name
Peptide deformylase
Molecular Weight
20038.335 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:34 / Updated at June 12, 2020 16:52