Explore a selection of our essential drug information below, or:
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
Structure for Arotinoid acid (DB02877)
- 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
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism ARetinoic acid receptor beta inhibitorHumans - 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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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
- External Links
- 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
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 240-241 °C Not Available - Predicted Properties
Property Value Source Water Solubility 0.000144 mg/mL ALOGPS logP 6.93 ALOGPS logP 6.9 Chemaxon logS -6.4 ALOGPS pKa (Strongest Acidic) 4.12 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 108.58 m3·mol-1 Chemaxon Polarizability 41.77 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9189 Caco-2 permeable + 0.7811 P-glycoprotein substrate Substrate 0.6352 P-glycoprotein inhibitor I Non-inhibitor 0.7403 P-glycoprotein inhibitor II Non-inhibitor 0.7206 Renal organic cation transporter Non-inhibitor 0.8568 CYP450 2C9 substrate Non-substrate 0.7375 CYP450 2D6 substrate Non-substrate 0.9108 CYP450 3A4 substrate Substrate 0.6559 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.7578 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.8756 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6966 Ames test Non AMES toxic 0.8226 Carcinogenicity Non-carcinogens 0.7904 Biodegradation Not ready biodegradable 0.848 Rat acute toxicity 2.1112 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9776 hERG inhibition (predictor II) Non-inhibitor 0.8891
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 211.1420659 predictedDarkChem Lite v0.1.0 [M-H]- 211.1377659 predictedDarkChem Lite v0.1.0 [M-H]- 185.85907 predictedDeepCCS 1.0 (2019) [M+H]+ 188.24498 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.50438 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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 expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence or presence of hormone ligand, acts mainly as an activator of gene expression due to weak binding to corepressors (PubMed:12554770). The RXRA/RARB heterodimer can act as a repressor on the DR1 element and as an activator on the DR5 element (PubMed:29021580). In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity)
- Specific Function
- Dna binding
- Gene Name
- RARB
- Uniprot ID
- P10826
- Uniprot Name
- Retinoic acid receptor beta
- Molecular Weight
- 50488.63 Da
References
- 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]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22