Details of the Drug

General Information of Drug (ID: DMSABD0)

Drug Name
TTNPB
Synonyms
Arotinoid acid; 71441-28-6; Arotinoic acid; Ro 13-7410; CCRIS 3297; UNII-673M8C29UR; 4-[(E)-2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid; Tocris-0761; Lopac-T-3757; TTNPB (Arotinoid Acid); BRN 2008247; CHEMBL275311; CHEBI:75261; 673M8C29UR; 4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid; (E)-4-(2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propen-1-yl)benzoic acid
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 348.5
Logarithm of the Partition Coefficient (xlogp) 7.5
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C24H28O2
IUPAC Name
4-[(E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzoic acid
Canonical SMILES
C/C(=C\\C1=CC=C(C=C1)C(=O)O)/C2=CC3=C(C=C2)C(CCC3(C)C)(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
Cross-matching ID
PubChem CID
5289501
ChEBI ID
CHEBI:75261
CAS Number
71441-28-6
UNII
673M8C29UR
DrugBank ID
DB02877
TTD ID
D0G6JM

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Retinoic acid receptor beta (RARB) TTISP28 RARB_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [3]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [3]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [4]
Bile acid receptor (NR1H4) OTWZLPTB NR1H4_HUMAN Gene/Protein Processing [5]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Protein Interaction/Cellular Processes [6]
Cytochrome P450 26A1 (CYP26A1) OTL1DFWV CP26A_HUMAN Gene/Protein Processing [7]
Cytochrome P450 4F11 (CYP4F11) OTHZ2GG2 CP4FB_HUMAN Gene/Protein Processing [8]
G1/S-specific cyclin-D1 (CCND1) OT8HPTKJ CCND1_HUMAN Gene/Protein Processing [9]
G1/S-specific cyclin-D3 (CCND3) OTNKPQ22 CCND3_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Retinoic acid receptor beta (RARB) DTT RARB 9.92E-02 -0.05 -0.21
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2646).
2 9-cis-retinoic acid analogues with bulky hydrophobic rings: new RXR-selective agonists. Bioorg Med Chem Lett. 2004 Dec 20;14(24):6117-22.
3 [Receptor-related mechanism of proliferation inhibilion and apoptosis induetion of human tongue squamous cell line Tca8113 by retinoids]. Di Yi Jun Yi Da Xue Xue Bao. 2005 Aug;25(8):935-41.
4 Modulation of aromatase activity and mRNA by various selected pesticides in the human choriocarcinoma JEG-3 cell line. Toxicology. 2006 Nov 10;228(1):98-108.
5 The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution. Am J Physiol Regul Integr Comp Physiol. 2007 Sep;293(3):R1400-9. doi: 10.1152/ajpregu.00781.2006. Epub 2007 Jun 13.
6 Retinoids inhibit proliferation of human coronary smooth muscle cells by modulating cell cycle regulators. Arterioscler Thromb Vasc Biol. 2001 May;21(5):746-51. doi: 10.1161/01.atv.21.5.746.
7 Activation of retinoic acid receptor-dependent transcription by organochlorine pesticides. Toxicol Appl Pharmacol. 2005 Jan 1;202(1):38-49.
8 Gene regulation of CYP4F11 in human keratinocyte HaCaT cells. Drug Metab Dispos. 2010 Jan;38(1):100-7. doi: 10.1124/dmd.109.029025.
9 Receptor-selective retinoids inhibit the growth of normal and malignant breast cells by inducing G1 cell cycle blockade. Breast Cancer Res Treat. 2006 Mar;96(2):147-57. doi: 10.1007/s10549-005-9071-1. Epub 2005 Nov 5.