Arotinoid acid

Identification

Name
Arotinoid acid
Accession Number
DB02877  (EXPT03128)
Type
Small Molecule
Groups
Experimental
Description

Arotinoid acid is a retinoic acid analog which acts as a selective RAR agonist.

Structure
Thumb
Synonyms
  • (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylenyl)-1 -propenyl] benzoic acid
  • TTNPB
External IDs
AGN-191183 / CCRIS 3297 / Lopac-T-3757 / RO 13-7410 / RO-137410 / T3757_SIGMA
Categories
UNII
673M8C29UR
CAS number
71441-28-6
Weight
Average: 348.4779
Monoisotopic: 348.20893014
Chemical Formula
C24H28O2
InChI Key
FOIVPCKZDPCJJY-JQIJEIRASA-N
InChI
InChI=1S/C24H28O2/c1-16(14-17-6-8-18(9-7-17)22(25)26)19-10-11-20-21(15-19)24(4,5)13-12-23(20,2)3/h6-11,14-15H,12-13H2,1-5H3,(H,25,26)/b16-14+
IUPAC Name
4-[(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl]benzoic acid
SMILES
C\C(=C/C1=CC=C(C=C1)C(O)=O)C1=CC=C2C(=C1)C(C)(C)CCC2(C)C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
URetinoic acid receptor betaNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of TTNPB.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of TTNPB.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of TTNPB.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with TTNPB.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of TTNPB.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of TTNPB.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of TTNPB.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of TTNPB.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of TTNPB.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with TTNPB.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of TTNPB.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of TTNPB.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of TTNPB.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of TTNPB.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of TTNPB.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with TTNPB.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of TTNPB.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of TTNPB.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of TTNPB.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C15634
PubChem Compound
5289501
PubChem Substance
46507753
ChemSpider
4451454
BindingDB
50032219
ChEBI
75261
ChEMBL
CHEMBL275311
IUPHAR
2646
Guide to Pharmacology
GtP Drug Page
HET
TTB
PDB Entries
1xap / 4dm6
MSDS
Download (35.7 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)240-241 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000144 mg/mLALOGPS
logP6.93ALOGPS
logP6.9ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity108.58 m3·mol-1ChemAxon
Polarizability41.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9189
Caco-2 permeable+0.7811
P-glycoprotein substrateSubstrate0.6352
P-glycoprotein inhibitor INon-inhibitor0.7403
P-glycoprotein inhibitor IINon-inhibitor0.7206
Renal organic cation transporterNon-inhibitor0.8568
CYP450 2C9 substrateNon-substrate0.7375
CYP450 2D6 substrateNon-substrate0.9108
CYP450 3A4 substrateSubstrate0.6559
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.7578
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8756
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6966
Ames testNon AMES toxic0.8226
CarcinogenicityNon-carcinogens0.7904
BiodegradationNot ready biodegradable0.848
Rat acute toxicity2.1112 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9776
hERG inhibition (predictor II)Non-inhibitor0.8891
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-02di-2981000000-d10a915aaa16a9e18de7

Taxonomy

Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Tetralins / Benzoic acids / Styrenes / Benzoyl derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Stilbene / Tetralin / Benzoic acid or derivatives / Benzoic acid / Benzoyl / Styrene / Monocyclic benzene moiety / Benzenoid / Monocarboxylic acid or derivatives / Carboxylic acid
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
retinoid, naphthalenes, benzoic acids (CHEBI:75261)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RARB
Uniprot ID
P10826
Uniprot Name
Retinoic acid receptor beta
Molecular Weight
50488.63 Da
References
  1. Alvarez R, Vega MJ, Kammerer S, Rossin A, Germain P, Gronemeyer H, de Lera AR: 9-cis-retinoic acid analogues with bulky hydrophobic rings: new RXR-selective agonists. Bioorg Med Chem Lett. 2004 Dec 20;14(24):6117-22. [PubMed:15546741]
  2. 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:20