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GLASS

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Go to the GPCR, ligand, or experimental data tables.
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GPCR

Name	Smoothened homolog
Species	Homo sapiens (Human)
Gene	SMO
Synonym	smoothened, frizzled class receptor smoothened SMOH SMO Protein Gx FZD11 frizzled family member 11 bnb [ Show all ]
Disease	N/A
Length	787
Amino acid sequence	MAAARPARGPELPLLGLLLLLLLGDPGRGAASSGNATGPGPRSAGGSARRSAAVTGPPPPLSHCGRAAPCEPLRYNVCLGSVLPYGATSTLLAGDSDSQEEAHGKLVLWSGLRNAPRCWAVIQPLLCAVYMPKCENDRVELPSRTLCQATRGPCAIVERERGWPDFLRCTPDRFPEGCTNEVQNIKFNSSGQCEVPLVRTDNPKSWYEDVEGCGIQCQNPLFTEAEHQDMHSYIAAFGAVTGLCTLFTLATFVADWRNSNRYPAVILFYVNACFFVGSIGWLAQFMDGARREIVCRADGTMRLGEPTSNETLSCVIIFVIVYYALMAGVVWFVVLTYAWHTSFKALGTTYQPLSGKTSYFHLLTWSLPFVLTVAILAVAQVDGDSVSGICFVGYKNYRYRAGFVLAPIGLVLIVGGYFLIRGVMTLFSIKSNHPGLLSEKAASKINETMLRLGIFGFLAFGFVLITFSCHFYDFFNQAEWERSFRDYVLCQANVTIGLPTKQPIPDCEIKNRPSLLVEKINLFAMFGTGIAMSTWVWTKATLLIWRRTWCRLTGQSDDEPKRIKKSKMIAKAFSKRHELLQNPGQELSFSMHTVSHDGPVAGLAFDLNEPSADVSSAWAQHVTKMVARRGAILPQDISVTPVATPVPPEEQANLWLVEAEISPELQKRLGRKKKRRKRKKEVCPLAPPPELHPPAPAPSTIPRLPQLPRQKCLVAAGAWGAGDSCRQGAWTLVSNPFCPEPSPPQDPFLPSAPAPVAWAHGRRQGLGPIHSRTNLMDTELMDADSDF
UniProt	Q99835
Protein Data Bank	4jkv, 4n4w, 4o9r, 4qim, 4qin, 5l7d, 5l7i, 5v56, 5v57
GPCR-HGmod model	N/A
3D structure model	This structure is from PDB ID 4jkv.
BioLiP	BL0352216, BL0270837, BL0267121, BL0267120, BL0243904,BL0243905, BL0283868, BL0283867, BL0352217,BL0352218, BL0352219,BL0352220, BL0379427,BL0379429, BL0379428,BL0379430, BL0379431,BL0379433, BL0379432,BL0379434
Therapeutic Target Database	N/A
ChEMBL	CHEMBL5971
IUPHAR	239
DrugBank	BE0004659

Ligand

Name	Vismodegib
Molecular formula	C19H14Cl2N2O3S
IUPAC name	2-chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide
Molecular weight	421.292
Hydrogen bond acceptor	4
Hydrogen bond donor	1
XlogP	3.8
Synonyms	GDC-0449 GDC-449 HY-10440 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methyl sulfonyl)benzamide MLS006012035 2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-(methylsulfonyl)benzamide NSC747691 AB0008125 RG-3616 ANW-60962 ST24040458 BDBM50249522 Vismodegib (SHH inhibitor) CHEMBL473417 ZINC40899447 DB08828 Erivedge (TN) GDC-0449(Vismodegib) Hh-Antag691 KB-308771 2-chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide NCGC00242497-02 4CA-1325 PubChem19137 AC-26969 SC-87729 AX8167197 UNII-25X868M3DS BPQMGSKTAYIVFO-UHFFFAOYSA-N Vismodegib, free base CUR-691 GD 0449\|\|\|2-Chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(methylsulfonyl)benzamide GDC-0449,Vismodegib HMS3654E17 2-chloro-n-(4-chloro-3-(2-pyridinyl)phenyl)-4-(methylsulfonyl)benzamide MCULE-6680076172 2-chloro-N-[4-chloro-3-(2-pyridyl)phenyl]-4-methylsulfonyl-benzamide NSC-747691 879085-55-9 R 3616 AKOS015966534 SR-01000941574 BCP9000713 CHEBI:66903 vismodegibum D0LB7J GDC-0449 (Vismodegib) GDC0449 J-509076 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide MolPort-009-679-417 2-chloro-N~1~-[4-chloro-3-(2-pyridyl)phenyl]-4-(methylsulfonyl)benzamide NSC755986 AB01565813_02 RL05479 AOB1040 SW218087-2 Benzamide, 2-chloro-N-(4-chloro-3-(2-pyridinyl)phenyl)-4-(methylsulfonyl)- Vismodegib (USAN/INN) CS-0255 DTXSID40236689 EX-A2178 GDC-0449(Vismodegib)/GDC0449 HhAntag691 085G559 KB-81450 2-CHLORO-N-[4-CHLORO-3-(2-PYRIDINYL)PHENYL]-4-(METHYLSULFONYL)-BENZAMIDE NCGC00242497-06 Q-2305 AJ-103831 SCHEMBL302587 BC660083 V-4050 C19H14Cl2N2O3S Vismodegib; GDC-0449 D03EDQ GDC 0449 GDC-0449,Vismodegib, HhAntag691 HSDB 8130 2-Chloro-N-(4-chloro-3-(2-pyridl)phenyl)-4-(methylsulfonyl)benzamide methanesulfonylbenzamide 2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4- NSC-755986 A10467 R-3616 AN-471 SR-01000941574-1 BCPP000223 Vismodegib (GDC-0449) X4669 Erivedge GDC-0449 - Selumetinib GTPL6975 J90022 2-chloro-N-(4-chloro-3-pyridin-2-yl-phenyl)-4-methanesulfonyl-benzamide NCGC00242497-01 25X868M3DS PB15086 ABP000894 s1082 AS-14066 TC-149707 BG0661 Vismodegib [USAN:INN] CTK8B8648 FT-0675833 GDC-0449, GDC0449, GDC 0449, 879085-55-9 HMS3604K16 2-Chloranyl-~{n}-(4-Chloranyl-3-Pyridin-2-Yl-Phenyl)-4-Methylsulfonyl-Benzamide KS-000000BH 2-Chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(methylsulfonyl)benzamide NSC 747691 QCR-40 AK-77261 SMR004703564 BCP01715 VIS C538724000 Vismodegib; HhAntag 691 D09992 [ Show all ]
Inchi Key	BPQMGSKTAYIVFO-UHFFFAOYSA-N
Inchi ID	InChI=1S/C19H14Cl2N2O3S/c1-27(25,26)13-6-7-14(17(21)11-13)19(24)23-12-5-8-16(20)15(10-12)18-4-2-3-9-22-18/h2-11H,1H3,(H,23,24)
PubChem CID	24776445
ChEMBL	CHEMBL473417
IUPHAR	6975
BindingDB	50249522
DrugBank	DB08828
Structure SDF download
Lipinski's druglikeness	This ligand satisfies Lipinski's rule of five.

Experimental Data

Parameter	Value	Reference	Database source
	N/A	N/A	DrugBank
IC50	5.1 nM	MedChemComm, (2016) 7:5:960	ChEMBL
IC50	6.0 nM	MedChemComm, (2015) 6:6:1137	ChEMBL
IC50	7.0 nM	PMID22268551	BindingDB,ChEMBL
IC50	20.0 nM	PMID24491459	BindingDB,ChEMBL
IC50	23.0 nM	PMID24726807	BindingDB,ChEMBL
IC50	33.0 nM	PMID24491459	BindingDB,ChEMBL
Inhibition	97.0 %	PMID22268551	ChEMBL
Inhibition	100.0 %	PMID22268551	ChEMBL
Ki	16.2 nM	PMID23063522	IUPHAR
Ki	16.2 nM	PMID23063522	BindingDB,ChEMBL

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