NAV

Arotinoid acid

Identification

Generic Name
Arotinoid acid
DrugBank Accession Number
DB02877
Background

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

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 348.4779
Monoisotopic: 348.20893014
Chemical Formula
C24H28O2
Synonyms
  • (E)-4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propen-1-yl)benzoic acid
  • Arotinoic acid
  • Arotinoid acid
  • TTNPB
External IDs
  • AGN 191183
  • AGN-191183
  • CCRIS 3297
  • Lopac-T-3757
  • RO 13-7410
  • RO-137410
  • T3757_SIGMA
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
URetinoic acid receptor betaNot 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
Chemical TaxonomyProvided by Classyfire
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
Aromatic homopolycyclic compound / Benzenoid / Benzoic acid / Benzoic acid or derivatives / Benzoyl / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
retinoid, naphthalenes, benzoic acids (CHEBI:75261)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
673M8C29UR
CAS number
71441-28-6
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

References

General References
Not Available
KEGG Compound
C15634
PubChem Compound
5289501
PubChem Substance
46507753
ChemSpider
4451454
BindingDB
50032219
ChEBI
75261
ChEMBL
CHEMBL275311
ZINC
ZINC000004475360
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
TTB
PDB Entries
1xap / 4dm6
MSDS
Download (35.7 KB)

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
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-01q9-2920000000-059b2df1e36fea7df1b8
MS/MS Spectrum - , positiveLC-MS/MSsplash10-02di-2981000000-d10a915aaa16a9e18de7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-0019000000-7b4525b6bd8db3de672e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-8fa21505a154f9d0120b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1039000000-0cbe7e907e8c3c34c3fe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0029000000-35eef736e7650abe30f9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0191000000-59430230808b9195a9c4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fvi-3296000000-bd8c4683d43c01f9ced0
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]-211.1420659
predicted
DarkChem Lite v0.1.0
[M-H]-211.1377659
predicted
DarkChem Lite v0.1.0
[M-H]-185.85907
predicted
DeepCCS 1.0 (2019)
[M+H]+188.24498
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.50438
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Retinoic acid receptor beta
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52