4-[(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl]benzoic acid

• ChemBase ID: 2589
• Molecular Formular: C24H28O2
• Molecular Mass: 348.47792
• Monoisotopic Mass: 348.20893014
• SMILES: C/C(=C\c1ccc(cc1)C(=O)O)/c1ccc2c(c1)C(C)(C)CCC2(C)C
• Canonical SMILES: C/C(=C\c1ccc(cc1)C(=O)O)/c1ccc2c(c1)C(C)(C)CCC2(C)C
• 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+
• InChIKey: FOIVPCKZDPCJJY-JQIJEIRASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl]benzoic acid
• IUPAC Traditional name: ttnpb
• Synonyms: (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylenyl)-1 -propenyl] benzoic acid; Arotinoid acid; Ro 13-7410; Arotinoic acid; Tocris-0761; Lopac-T-3757; T3757_SIGMA; CCRIS 3297; TTNPB; 4-[(E)-2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid; TTNPB

Database IDs

• CAS Number: 71441-28-6
• MDL Number: MFCD00673917
• PubChem SID: 160966038; 46507753; 24278733
• PubChem CID: 5289501

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.1158433
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.49782
• LogD (pH = 7.4): 3.8075383
• Log P: 6.896451
• Molar Refractivity: 108.5806 cm^3
• Polarizability: 41.56039 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.93
• LOG S: -6.38
• Solubility (Water): 1.44e-04 g/l

PROPERTIES

Safety Information

• RTECS: DH6834900
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-61-36/37/38
• Safety Statements: 53-26-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H360
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Pharmacology Properties

• Target: Others
• Gene Information: human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB02877

• Drug Groups: experimental
• Description: TTNPB is a retinoic acid analog which acts as a selective RAR agonist.
• Affected Organisms: Humans and other mammals

Sigma Aldrich - T3757

Biochem/physiol Actions
Selective and highly potent retinoic acid analog with affinity for retinoic acid receptors (RAR) α, β, and γ, which are nuclear transcription factors. Produces ligand-activated transcription of genes that possess retinoic acid responsive elements.