NAV

{3-[3-(3,4-Dimethoxy-Phenyl)-1-(1-{1-[2-(3,4,5-Trimethoxy-Phenyl)-Butyryl]-Piperidin-2yl}-Vinyloxy)-Propyl]-Phenoxy}-Acetic Acid

Identification

Generic Name
{3-[3-(3,4-Dimethoxy-Phenyl)-1-(1-{1-[2-(3,4,5-Trimethoxy-Phenyl)-Butyryl]-Piperidin-2yl}-Vinyloxy)-Propyl]-Phenoxy}-Acetic Acid
DrugBank Accession Number
DB01723
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 693.7799
Monoisotopic: 693.314911351
Chemical Formula
C38H47NO11
Synonyms
Not Available
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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
UPeptidyl-prolyl cis-trans isomerase FKBP1ANot AvailableHumans
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as linear 1,3-diarylpropanoids. These are organic compounds with a structure based on a C6-C3-C6 skeleton, where the two benzene rings are not linked together.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Linear 1,3-diarylpropanoids
Sub Class
Not Available
Direct Parent
Linear 1,3-diarylpropanoids
Alternative Parents
Alpha amino acid esters / Phenoxyacetic acid derivatives / Phenylacetamides / Dimethoxybenzenes / Benzyloxycarbonyls / Piperidinecarboxylic acids / Phenylpropanes / N-acylpiperidines / Phenoxy compounds / Anisoles
show 11 more
Substituents
Alkyl aryl ether / Alpha-amino acid ester / Alpha-amino acid or derivatives / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbonyl group / Carboxamide group
show 27 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XCCRAOPQCACRFC-OIFRRMEBSA-N
InChI
InChI=1S/C38H47NO11/c1-7-28(26-21-33(46-4)36(48-6)34(22-26)47-5)37(42)39-18-9-8-13-29(39)38(43)50-30(25-11-10-12-27(20-25)49-23-35(40)41)16-14-24-15-17-31(44-2)32(19-24)45-3/h10-12,15,17,19-22,28-30H,7-9,13-14,16,18,23H2,1-6H3,(H,40,41)/t28-,29-,30+/m0/s1
IUPAC Name
2-{3-[(1R)-3-(3,4-dimethoxyphenyl)-1-[(2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidine-2-carbonyloxy]propyl]phenoxy}acetic acid
SMILES
[H][C@](CCC1=CC(OC)=C(OC)C=C1)(OC(=O)[C@]1([H])CCCCN1C(=O)[C@@]([H])(CC)C1=CC(OC)=C(OC)C(OC)=C1)C1=CC(OCC(O)=O)=CC=C1

References

General References
Not Available
PubChem Compound
444590
PubChem Substance
46506401
ChemSpider
392474
BindingDB
50132541
ChEMBL
CHEMBL110674
ZINC
ZINC000024433235
PDBe Ligand
AP1
PDB Entries
1bl4

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 Solubility0.00094 mg/mLALOGPS
logP5.32ALOGPS
logP5.7Chemaxon
logS-5.9ALOGPS
pKa (Strongest Acidic)3.44Chemaxon
pKa (Strongest Basic)-1.5Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area139.29 Å2Chemaxon
Rotatable Bond Count18Chemaxon
Refractivity184.01 m3·mol-1Chemaxon
Polarizability74.68 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6539
Blood Brain Barrier+0.6435
Caco-2 permeable+0.5442
P-glycoprotein substrateSubstrate0.6839
P-glycoprotein inhibitor IInhibitor0.5973
P-glycoprotein inhibitor IIInhibitor0.7257
Renal organic cation transporterNon-inhibitor0.7286
CYP450 2C9 substrateNon-substrate0.8215
CYP450 2D6 substrateNon-substrate0.8441
CYP450 3A4 substrateSubstrate0.6873
CYP450 1A2 substrateNon-inhibitor0.693
CYP450 2C9 inhibitorNon-inhibitor0.6915
CYP450 2D6 inhibitorNon-inhibitor0.8835
CYP450 2C19 inhibitorNon-inhibitor0.774
CYP450 3A4 inhibitorNon-inhibitor0.754
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7514
Ames testNon AMES toxic0.8454
CarcinogenicityNon-carcinogens0.919
BiodegradationNot ready biodegradable0.7628
Rat acute toxicity2.3600 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9522
hERG inhibition (predictor II)Inhibitor0.5104
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090102000-9c2b2906fcdd6e266f09
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-5202903000-072e0dd9bc77590ed09d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0090001000-118f77b70e0af714b85b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06rf-1391013000-68aa2028d891f73c9391
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0m2i-0937103000-e412ae2063a7b6054137
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002e-3922408000-d9ab34dd623e2b218b48
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-241.9904
predicted
DeepCCS 1.0 (2019)
[M+H]+243.73454
predicted
DeepCCS 1.0 (2019)
[M+Na]+249.80046
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peptidyl-prolyl cis-trans isomerase FKBP1A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Type i transforming growth factor beta receptor binding
Specific Function
Keeps in an inactive conformation TGFBR1, the TGF-beta type I serine/threonine kinase receptor, preventing TGF-beta receptor activation in absence of ligand. Recruites SMAD7 to ACVR1B which prevent...
Gene Name
FKBP1A
Uniprot ID
P62942
Uniprot Name
Peptidyl-prolyl cis-trans isomerase FKBP1A
Molecular Weight
11950.665 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:51