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- ChemComp-ROC: (2S)-N-[(2S,3R)-4-[(2S,3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a... -

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Basic information

EntryDatabase: PDB chemical components / ID: ROC
NameName: (2S)-N-[(2S,3R)-4-[(2S,3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1
Synonyms: Fortovase; SAQUINAVIR; RO 31-8959
WikipediaWikipedia - Saquinavir:

Saquinavir, sold under the brand name Invirase among others, is an antiretroviral medication used together with other medications to treat or prevent HIV/AIDS. Typically it is used with ritonavir or lopinavir/ritonavir to increase its effect...

Commentmedication, antiretroviral*YM

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BIRD information

TypePeptide-like / Inhibitor
DownloadsMolecular definition / Chemical definition / Family definition
Synonyms
  • (2S)-N~1~ -{(1S,2R)-1-Benzyl-3-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octah ydroisochinolin-2(1H)-yl]-2-hydroxypropyl}-2-[(chinolin-2-ylcar bonyl)amino]butandiamid (ChemSpider)
  • (2S)-N~1~ -{(1S,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octah ydroisoquinolin-2(1H)-yl]-2-hydroxypropyl}-2-[(quinolin-2-ylcar bonyl)amino]butanediamide (ChemSpider)
  • (2S)-N~1~ -{(1S,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-[(1,1-dimthylthyl)carbam oyl]octahydroisoquinolin-2(1H)-yl]-2-hydroxypropyl}-2-[(quinol in-2-ylcarbonyl)amino]butanediamide (ChemSpider)
  • (S)-N%1&-[(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-2-[(quinoline-2-carbonyl)-amino]-succinamide (Beilstein)
  • (S)-N-[(a S)-a-[(1R)-2-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydro-2(1 H)-isoquinolyl]-1-hydroxyethyl]phenethyl]-2-quinaldamidosuccina midecarbonyl)amino]butanediamide (ChemSpider)
  • (S)-N-[(alphaS)-alpha-[(1R)-2-[(3S,4aS,8aS)-3-(tert-Butylcarbamoyl)octahydro-2(1H)-isoquinolyl]-1-hydroxyethyl] phenethyl]-2-quinaldamidosuccinamide (Scifinder)
  • (S)-N-[(alphaS)-alpha-[(1R)-2-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydro-2(1H)-isoquinolyl]-1-hydroxyethyl] phenethyl]-2-quinaldamido succinamide (Merck)
  • (S)-N-[(alphaS)-alpha-[(1R)-2-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydro-2(1H)-isoquinolyl]-1-hydroxyethyl] phenethyl]-2-quinaldamidosuccinamide (ChemBank)
  • (S)-N-[(alphaS)-alpha-[(1R)-2-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydro-2(1H)-isoquinolyl]-1-hydroxyethyl] phenethyl]-2-quinaldamidosuccinamide monomethanesulfonate (salt) (ChemBank)
  • 2S)-N1[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-Dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]butanediamide (Merck)
  • Butanediamide, N1-((1S,2R)-3-((3S,4aS,8aS)-3-(((1,1-dimethylethyl)amino)carbonyl)octahydro-2(1H)-isoquinolinyl)-2-hydroxy-1-(phenylmeth yl)propyl)-2-((2-quinolinylcarbonyl)amino)-, (2S)-e (ChemSpider)
  • Butanediamide, N1-[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-, (2S)- (Scifinder)
  • Butanediamide, N1-[3-[3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-, [3S-[2[1R*(R*),2S*],3alpha,4alpha beta,8alpha beta]]- (Scifinder)
  • FortovaseSaquinavir (PDB, Scifinder, Beilstein, KEGG, DrugBank, PubChem)
  • InviraseSaquinavir (DrugBank, ChemBank)
  • L-aspartamide, N~1~-[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amin o]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-N~2~-(2-quinolinylcarbonyl)-)-, (2S)-e (ChemSpider)
  • N-tert-Bu tyldecahydro-2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-asparaginyl]amino]butyl](4aS,8aS)-isoquinoline-3(S)-carboxamidespartamide-(2-quinolinylcarbonyl)-)-, (2S)-e (ChemSpider)
  • N-tert-butyldecahydro-2-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-asparaginyl]amino]butyl](4aS,8aS)-isoquinoline-3(S)-carboxamide (Merck)
  • N~1~-{(1R,2R)-1-benzyl-3-[(3S,4aR,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-2-hydroxypropyl}-N~2~-(quinolin-2-ylcarbonyl)-D-aspartamide (ChemBank)
  • N~1~-{(1S ,2R)-1-benzyl-3-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-2-hydroxypropyl}-N~2~-(quinolin-2-ylcarbon yl)-L-aspartamide-(2-quinolinylcarbonyl)-)-, (2S)-e (ChemSpider)
  • N~1~-{1-benzyl-3-[3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-2-hydroxypropyl}-N~2~-(quinolin-2-ylcarbonyl)aspartamide (ChemBank)
  • ROC (DrugBank)
  • Ro 31-8959Saquinavir (Scifinder, Beilstein)
  • Ro 31-8959/000 (Beilstein)
  • Ro-31-8959 (Merck, Beilstein)
  • Ro31-8959 (Beilstein)
  • Ro318959 (Beilstein)
  • SAQUINAVIR (eMolecules)
  • SQV (DrugBank)
  • Saquinavir (Scifinder, KEGG, PubChem, eMolecules)
  • Saquinavir MesylateSaquinavir (DrugBank)
  • Saquinavir, Mesylate (eMolecules)
  • Saquinavir-d9 (eMolecules)
  • Sch 52852 (Scifinder)
  • Sequinavir (Scifinder)
  • [3S-[2[1R *(R*),2S*],3a,4ab,8ab]]-N1[3-[3-[[(1,1-Dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoqu inolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcar bonyl)amino]butanediamide (ChemSpider)
  • butanediamide,N1-[3-[3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-,[3S-[2[1R*(R*) ,2S*],3alpha,4abeta,8abeta]]- (ChemBank)
  • butanediamide,N1-[3-[3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-,[3S-[2[1R*(R*),2S*],3alpha,4abeta,8abeta]]-, monomethanesulfonate (salt) (ChemBank)
  • saquinavir (Beilstein, DrugBank, ChemBank, eMolecules)
  • saquinavir mesilate (ChemBank)
  • saquinavir mesylateSaquinavir (ChemBank)
Annotation
  • Function: Inhibitor of HIV-1 PROTEASE, EC: 3.4.23.16EC: Inhibitor of HIV-1 PROTEASE, EC: 3.4.23.16 / Info source: PubMed: 1956054
  • Function: Antiviral activity [HIV protease inhibitor] / Info source: KEGG
  • Function: protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1) / Info source: DrugBank
  • Function: antiretroviral drug used in HIV therapy. It falls in the protease inhibitor class. / Info source: Wikipedia
  • Function: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases. (Description, from PubChem) / Info source: DrugBank
  • Pharmacological action: Saquinavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Saquinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs. (Pharmacodynamics) / Info source: DrugBank
  • Mechanism of action: Saquinavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles. (Mechanism of action) / Info source: DrugBank
External info
FamilySAQUINAVIR

Saquinavir

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Chemical information

Composition
Formula: C38H50N6O5 / Number of atoms: 99 / Formula weight: 670.841 / Formal charge: 0
Others

1hxb

QNC

ASN

HP0

NTB

Type: peptide-like / PDB classification: HETAIN / Three letter code: ROC / Ideal coordinates details: Corina / Model coordinates PDB-ID: 1HXB / Model coordinates details: not provided / Subcomponent: QNC, ASN, HP0, NTB
History
Other modificationJan 4, 2000
Other modificationOct 17, 2010
Modify aromatic flagJun 4, 2011
Modify descriptorJun 4, 2011
Other modificationNov 15, 2011
Modify synonymsJun 5, 2020
Modify synonymsJul 2, 2020
Other modificationAug 12, 2020
External linksUniChem / BindingDB / Brenda / ChEBI / ChEMBL / ChemicalBook / CompTox / DailyMed / DrugBank / GtoPharmacology / Nikkaji / PubChem / PubChem_TPharma / SureChEMBL / ZINC / ChemSpider / Wikipedia search / Google search

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Structure visualization

Structure viewerMolecule:
MolmilJmol/JSmol

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Details

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SMILES

ACDLabs 12.01O=C(N)CC(NC(=O)c1nc2c(cc1)cccc2)C(=O)NC(Cc3ccccc3)C(O)CN5C(C(=O)NC(C)(C)C)CC4C(CCCC4)C5
CACTVS 3.370CC(C)(C)NC(=O)[CH]1C[CH]2CCCC[CH]2CN1C[CH](O)[CH](Cc3ccccc3)NC(=O)[CH](CC(N)=O)NC(=O)c4ccc5ccccc5n4
OpenEye OEToolkits 1.7.0CC(C)(C)NC(=O)C1CC2CCCCC2CN1CC(C(Cc3ccccc3)NC(=O)C(CC(=O)N)NC(=O)c4ccc5ccccc5n4)O

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SMILES CANONICAL

CACTVS 3.370CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@@H](O)[C@H](Cc3ccccc3)NC(=O)[C@H](CC(N)=O)NC(=O)c4ccc5ccccc5n4
OpenEye OEToolkits 1.7.0CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2C[N@]1C[C@H]([C@H](Cc3ccccc3)NC(=O)[C@H](CC(=O)N)NC(=O)c4ccc5ccccc5n4)O

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InChI

InChI 1.03InChI=1S/C38H50N6O5/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49)/t26-,27+,30-,31-,32-,33+/m0/s1

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InChIKey

InChI 1.03QWAXKHKRTORLEM-UGJKXSETSA-N

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SYSTEMATIC NAME

ACDLabs 12.01N~1~-{(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}-N~2~-(quinolin-2-ylcarbonyl)-L-aspartamide
OpenEye OEToolkits 1.7.0(2S)-N-[(2S,3R)-4-[(2S,3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenyl-butan-2-yl]-2-(quinolin-2-ylcarbonylamino)butanediamide

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