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]
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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
CAS Number: 153559-76-3
DrugBank ID: DB01941
TTD ID: D0YO4D

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]

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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]
Apolipoprotein A-II (APOA2)	OTQ3HGTC	APOA2_HUMAN	Gene/Protein Processing	[4]
Aromatase (CYP19A1)	OTZ6XF74	CP19A_HUMAN	Gene/Protein Processing	[5]
Bile acid receptor (NR1H4)	OTWZLPTB	NR1H4_HUMAN	Gene/Protein Processing	[6]
Choriogonadotropin subunit beta 3 (CGB3)	OTVM2SU3	CGB3_HUMAN	Gene/Protein Processing	[7]
Cyclin-A2 (CCNA2)	OTPHHYZJ	CCNA2_HUMAN	Gene/Protein Processing	[8]
Cyclin-dependent kinase 2 (CDK2)	OTB5DYYZ	CDK2_HUMAN	Gene/Protein Processing	[8]
Cytochrome P450 4F11 (CYP4F11)	OTHZ2GG2	CP4FB_HUMAN	Gene/Protein Processing	[9]
DNA-binding protein inhibitor ID-1 (ID1)	OTKGNZN5	ID1_HUMAN	Gene/Protein Processing	[10]
G1/S-specific cyclin-D1 (CCND1)	OT8HPTKJ	CCND1_HUMAN	Gene/Protein Processing	[11]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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

Molecular Expression Atlas (MEA)

MEA Detail

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: 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	Retinoids increase human apolipoprotein A-11 expression through activation of the retinoid X receptor but not the retinoic acid receptor. Mol Cell Biol. 1996 Jul;16(7):3350-60. doi: 10.1128/MCB.16.7.3350.
5	Insulin sensitizer, troglitazone, directly inhibits aromatase activity in human ovarian granulosa cells. Biochem Biophys Res Commun. 2000 May 19;271(3):710-3.
6	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.
7	Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions. Mol Endocrinol. 2005 Oct;19(10):2502-16.
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	Gene regulation of CYP4F11 in human keratinocyte HaCaT cells. Drug Metab Dispos. 2010 Jan;38(1):100-7. doi: 10.1124/dmd.109.029025.
10	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.
11	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.