ChemComp-PI6: [1-BENZYL-3-(8-SEC-BUTYL-7,10-DIOXO-2-OXA-6,9-DIAZA-BICYCLO[11.2....

Basic information

• Entry: Database: PDB chemical components / ID: PI6
• Name: Name: [1-benzyl-3-(8-sec-butyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2] heptadeca-1(16),13(17),14-trien-11-ylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester; Synonyms: MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 6

BIRD information

• Type: Peptide-like / Inhibitor
• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 6 (PubChem)
• Phe-Ile-Val Macrocyclic mimetic (PubChem)
• [1-BENZYL-3-(8-SEC-BUTYL-7,10-DIOXO-2-OXA-6,9-DIAZA-BICYCLO[11.2.2] HEPTADECA-1(16),13(17),14-TRIEN-11-YLAMINO)-2-HYDROXY-PROPYL] -CARBAMIC ACID TERT-BUTYL ESTER (PubChem)

Annotation

• Function: inhibitor of retropepsin, EC: 3.4.23.16EC: inhibitor of retropepsin, EC: 3.4.23.16 / Info source: PubMed: 10387041

External info

• BindingDB: 13932
• ChemDB: 6916305
• ChemSpider: 392405
• ChEBI: 165658
• PubChem: 15297040
• PubChem: 444481

Family

ethyleneamine containing macrocyclic peptidomimetic inhibitor

tert-butyl [(1S,2S)-1-benzyl-2-hydroxy-3-{[(8S,11R)-8-[(1R)-1-methylpropyl]-7,10-dioxo-2-oxa-6,9-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-11-yl]amino}propyl]carbamate

Chemical information

Composition

Formula: C₃₃H₄₈N₄O₆ / Number of atoms: 91 / Formula weight: 596.757 / Formal charge: 0

Others

1mtr

BOC

T00

ILE

0D8

0EZ

Type: peptide-like / PDB classification: HETAIN / Three letter code: PI6 / Ideal coordinates details: Corina / Model coordinates PDB-ID: 1MTR / Subcomponent: BOC, T00, ILE, 0D8 / Replaces: 0EZ

History

Create component	Jul 8, 1999
Modify descriptor	Jun 4, 2011
Modify subcomponent list	Jul 19, 2012
Modify atom id	Jul 19, 2012
Modify model coordinates code	Jul 19, 2012
Modify synonyms	Mar 1, 2021

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C(OC(C)(C)C)NC(Cc1ccccc1)C(O)CNC3C(=O)NC(C(=O)NCCCOc2ccc(cc2)C3)C(C)CC
• CACTVS 3.370: CC[CH](C)[CH]1NC(=O)[CH](Cc2ccc(OCCCNC1=O)cc2)NC[CH](O)[CH](Cc3ccccc3)NC(=O)OC(C)(C)C
• OpenEye OEToolkits 1.7.6: CCC(C)C1C(=O)NCCCOc2ccc(cc2)CC(C(=O)N1)NCC(C(Cc3ccccc3)NC(=O)OC(C)(C)C)O

SMILES CANONICAL

• CACTVS 3.370: CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(OCCCNC1=O)cc2)NC[C@@H](O)[C@H](Cc3ccccc3)NC(=O)OC(C)(C)C
• OpenEye OEToolkits 1.7.6: CC[C@H](C)[C@H]1C(=O)NCCCOc2ccc(cc2)C[C@@H](C(=O)N1)NC[C@H]([C@H](Cc3ccccc3)NC(=O)OC(C)(C)C)O

InChI

• InChI 1.03: InChI=1S/C33H48N4O6/c1-6-22(2)29-31(40)34-17-10-18-42-25-15-13-24(14-16-25)20-27(30(39)37-29)35-21-28(38)26(19-23-11-8-7-9-12-23)36-32(41)43-33(3,4)5/h7-9,11-16,22,26-29,35,38H,6,10,17-21H2,1-5H3,(H,34,40)(H,36,41)(H,37,39)/t22-,26-,27-,28+,29-/m0/s1

InChIKey

• InChI 1.03: RFUKEYSMPSCDLJ-CLFZCTPNSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: tert-butyl [(2S,3R)-4-{[(8S,11S)-8-[(2S)-butan-2-yl]-7,10-dioxo-2-oxa-6,9-diazabicyclo[11.2.2]heptadeca-1(15),13,16-trien-11-yl]amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate
• OpenEye OEToolkits 1.7.6: tert-butyl N-[(2S,3R)-4-[[(3S,6S)-6-[(2S)-butan-2-yl]-4,7-bis(oxidanylidene)-12-oxa-5,8-diazabicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-3-yl]amino]-3-oxidanyl-1-phenyl-butan-2-yl]carbamate

PDB entries

Showing all 2 items

PDB-1b6m:
HIV-1 PROTEASE COMPLEXED WITH MACROCYCLIC PEPTIDOMIMETIC INHIBITOR 6

PDB-1mtr:
HIV-1 PROTEASE COMPLEXED WITH A CYCLIC PHE-ILE-VAL PEPTIDOMIMETIC INHIBITOR