CAS 71441-28-6|(E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylenyl)-1 -propenyl] benzoic acid|ttnpb|Arotinoid acid|T3757_SIGMA|CCRIS 3297|TTNPB|Tocris-0761|4-[(1E)-2-(5,5,8,8-tetramethyl...

General Information

Structure

Molecular Formula

C₂₄H₂₈O₂

Molecular Mass

348.47792

Exact Mass

348.20893014

Charge

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

Canonic Smiles

C/C(=C\c1ccc(cc1)C(=O)O)/c1ccc2c(c1)C(C)(C)CCC2(C)C

Isomeric Smiles

C/C(=C\c1ccc(cc1)C(=O)O)/c1ccc2c(c1)C(C)(C)CCC2(C)C

Calculated Properties

JChem

LogD (pH = 7.4)

3.81

LogD (pH = 5.5)

5.50

Log P

6.90

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

4.12

Polar Surface Area

37.30

Polarizability

41.71

Molar Refractivity

108.58

LOG S

-7.69

Data Source

Names and Identifiers

Synonyms

T3757_SIGMAArotinoid acid(E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylenyl)-1 -propenyl] benzoic acidCCRIS 3297TTNPBTocris-0761Lopac-T-3757Arotinoic acidRo 13-7410TTNPB4-[(E)-2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acidArotinoic acidRo 13-7410arotinoid acidTTNPBAGN-191183CCRIS 3297

IUPAC Traditional name

ttnpb

IUPAC name

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

Names and Identifiers

Registration numbers

PubChem CID

5289501

CAS Number

71441-28-6

PubChem SID

4650775324278733160966038163835391

MDL Number

MFCD00673917

PubMed Citation Links

217518221559717196321631510927333786551376755

BRENDA Ligand Database

1236971525120161984514742

BRENDA Database

3.1.26.52.3.1.B412.4.1.129

CompTox Database

DTXSID6040743

ACToR Database

71441-28-6

BKMS React Database

1201614742198457152512369

KEGG ID

CHEMBL

Reaxys Registry

Patent number

PDBeChem Database

MetaboLights Database

MTBLS673

SureChEMBL Database

SCHEMBL177444

DrugBank ID

DB02877

CHEBI ID

CHEBI:75261CHEBI:46258

Protein Data Bank

1xap4dm6

BindingDB Database

50032219

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... RARA(5914), RARB(5915), RARG(5916), RXRA(6256), RXRB(6257), RXRG(6258)

Target

Others

Product Information

Salt Data

Free Base

Properties

Related Proteins

Molecular Spectra

No Data Available

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Molecule 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.

ChEBI

CHEBI:75261

A retinoid that consists of benzoic acid substituted at position 4 by a 2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl group. It is a synthetic retinoid that acts as a selective agonist for the retinoic acid receptors (RAR).

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity