Details of the Drug

General Information of Drug (ID: DM41RK2)

Drug Name
LG100268
Synonyms
AmbkkkkK580; LG 100268; LG2; LG-100268; 6-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl)nicotinic acid; 6-[1-(3,5,5,8,8-PENTAMETHYL-5,6,7,8-TETRAHYDRONAPHTHALEN-2-YL)CYCLOPROPYL]PYRIDINE-3-CARBOXYLIC ACID; 6-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopropyl]-nicotinic acid; 6-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Acquired immune deficiency syndrome 1C62.3 Discontinued in Phase 1 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 363.5
Logarithm of the Partition Coefficient (xlogp) 6.1
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C24H29NO2
IUPAC Name
6-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid
Canonical SMILES
CC1=CC2=C(C=C1C3(CC3)C4=NC=C(C=C4)C(=O)O)C(CCC2(C)C)(C)C
InChI
InChI=1S/C24H29NO2/c1-15-12-18-19(23(4,5)9-8-22(18,2)3)13-17(15)24(10-11-24)20-7-6-16(14-25-20)21(26)27/h6-7,12-14H,8-11H2,1-5H3,(H,26,27)
InChIKey
SLXTWXQUEZSSTJ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3922
ChEBI ID
CHEMBL288436
CAS Number
153559-76-3
UNII
UVU4X1103P
DrugBank ID
DB01941
TTD ID
D0YO4D
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Retinoic acid receptor alpha (RARA) TTW38KT RARA_HUMAN Agonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
17-beta-hydroxysteroid dehydrogenase type 1 (HSD17B1) OT6EBDHM DHB1_HUMAN Gene/Protein Processing [3]
Bile acid receptor (NR1H4) OTWZLPTB NR1H4_HUMAN Gene/Protein Processing [4]
Choriogonadotropin subunit beta 3 (CGB3) OTVM2SU3 CGB3_HUMAN Gene/Protein Processing [5]
Cytochrome P450 4F11 (CYP4F11) OTHZ2GG2 CP4FB_HUMAN Gene/Protein Processing [6]
DNA-binding protein inhibitor ID-1 (ID1) OTKGNZN5 ID1_HUMAN Gene/Protein Processing [7]
G1/S-specific cyclin-D3 (CCND3) OTNKPQ22 CCND3_HUMAN Gene/Protein Processing [8]
Nuclear receptor subfamily 5 group A member 2 (NR5A2) OTXAUJAS NR5A2_HUMAN Gene/Protein Processing [9]
Retinoblastoma-associated protein (RB1) OTQJUJMZ RB_HUMAN Post-Translational Modifications [10]
Stearoyl-CoA desaturase (SCD) OTB1073G SCD_HUMAN Gene/Protein Processing [7]
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Molecular Expression Atlas of This Drug

The Studied Disease Acquired immune deficiency syndrome
ICD Disease Classification 1C62.3
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Retinoic acid receptor alpha (RARA) DTT RARA 4.46E-01 -0.04 -0.13
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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: 2808).
2 Placental steroidogenesis in rats is independent of signaling pathways induced by retinoic acids. Gen Comp Endocrinol. 2009 Sep 15;163(3):285-91.
3 Organotin compounds enhance 17beta-hydroxysteroid dehydrogenase type I activity in human choriocarcinoma JAr cells: potential promotion of 17beta-estradiol biosynthesis in human placenta. Biochem Pharmacol. 2006 Apr 28;71(9):1349-57.
4 Retinoid X receptor (RXR) agonist-induced antagonism of farnesoid X receptor (FXR) activity due to absence of coactivator recruitment and decreased DNA binding. J Biol Chem. 2003 Mar 21;278(12):10028-32. doi: 10.1074/jbc.M208312200. Epub 2003 Jan 7.
5 Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions. Mol Endocrinol. 2005 Oct;19(10):2502-16.
6 Gene regulation of CYP4F11 in human keratinocyte HaCaT cells. Drug Metab Dispos. 2010 Jan;38(1):100-7. doi: 10.1124/dmd.109.029025.
7 Identification of biomarkers modulated by the rexinoid LGD1069 (bexarotene) in human breast cells using oligonucleotide arrays. Cancer Res. 2006 Dec 15;66(24):12009-18.
8 Thiazolidinediones inhibit proliferation of microvascular and macrovascular cells by a PPARgamma-independent mechanism. Diabetologia. 2005 Mar;48(3):586-94. doi: 10.1007/s00125-005-1672-z. Epub 2005 Feb 24.
9 Coactivation of liver receptor homologue-1 by peroxisome proliferator-activated receptor gamma coactivator-1alpha on aromatase promoter II and its inhibition by activated retinoid X receptor suggest a novel target for breast-specific antiestrogen therapy. Cancer Res. 2005 Dec 15;65(24):11762-70. doi: 10.1158/0008-5472.CAN-05-2792.
10 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.