ID: ALA529902

Max Phase: Preclinical

Molecular Formula: C184H280N50O64S

Molecular Weight: 4248.62

Molecule Type: Protein

Representations

Canonical SMILES:  CC[C@H](C)[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@@H](N)Cc1c[nH]c2ccccc12)[C@@H](C)CC)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)O

Standard InChI:  InChI=1S/C184H280N50O64S/c1-17-87(12)146(179(293)215-112(46-57-143(258)259)158(272)209-111(45-56-142(256)257)162(276)228-127(79-235)176(290)214-106(40-51-133(190)243)159(273)222-122(72-135(192)245)168(282)212-105(39-50-132(189)242)155(269)205-103(37-48-130(187)240)153(267)207-107(41-52-138(248)249)156(270)203-101(31-24-25-60-185)152(266)221-121(71-134(191)244)169(283)213-108(42-53-139(250)251)157(271)206-104(38-49-131(188)241)154(268)208-109(43-54-140(252)253)160(274)216-115(63-83(4)5)165(279)227-126(183(297)298)66-86(10)11)232-173(287)116(64-84(6)7)217-177(291)128(80-236)229-167(281)120(70-94-78-197-82-201-94)225-180(294)148(89(14)19-3)233-174(288)117(65-85(8)9)218-178(292)129(81-237)230-182(296)149(90(15)238)234-175(289)118(67-91-33-35-95(239)36-34-91)219-170(284)123(73-136(193)246)223-171(285)124(74-137(194)247)226-181(295)147(88(13)18-2)231-164(278)113(47-58-144(260)261)211-151(265)102(32-26-61-198-184(195)196)204-172(286)125(75-145(262)263)224-166(280)119(69-93-77-200-100-30-23-21-28-97(93)100)220-161(275)110(44-55-141(254)255)210-163(277)114(59-62-299-16)202-150(264)98(186)68-92-76-199-99-29-22-20-27-96(92)99/h20-23,27-30,33-36,76-78,82-90,98,101-129,146-149,199-200,235-239H,17-19,24-26,31-32,37-75,79-81,185-186H2,1-16H3,(H2,187,240)(H2,188,241)(H2,189,242)(H2,190,243)(H2,191,244)(H2,192,245)(H2,193,246)(H2,194,247)(H,197,201)(H,202,264)(H,203,270)(H,204,286)(H,205,269)(H,206,271)(H,207,267)(H,208,268)(H,209,272)(H,210,277)(H,211,265)(H,212,282)(H,213,283)(H,214,290)(H,215,293)(H,216,274)(H,217,291)(H,218,292)(H,219,284)(H,220,275)(H,221,266)(H,222,273)(H,223,285)(H,224,280)(H,225,294)(H,226,295)(H,227,279)(H,228,276)(H,229,281)(H,230,296)(H,231,278)(H,232,287)(H,233,288)(H,234,289)(H,248,249)(H,250,251)(H,252,253)(H,254,255)(H,256,257)(H,258,259)(H,260,261)(H,262,263)(H,297,298)(H4,195,196,198)/t87-,88-,89-,90+,98-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,146-,147-,148-,149-/m0/s1

Standard InChI Key:  KPWKCQJHMCGNLQ-MGEOPITOSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 4248.62

Molecular Weight (Monoisotopic): 4245.9913

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Nishikawa H, Oishi S, Fujita M, Watanabe K, Tokiwa R, Ohno H, Kodama E, Izumi K, Kajiwara K, Naitoh T, Matsuoka M, Otaka A, Fujii N..  (2008)  Identification of minimal sequence for HIV-1 fusion inhibitors.,  16  (20): [PMID:18819810] [10.1016/j.bmc.2008.09.018]

2. Oishi S, Kodera Y, Nishikawa H, Kamitani H, Watabe T, Ohno H, Tochikura T, Shimane K, Kodama E, Matsuoka M, Mizukoshi F, Tsujimoto H, Fujii N..  (2009)  Design and synthesis of membrane fusion inhibitors against the feline immunodeficiency virus.,  17  (14): [PMID:19541488] [10.1016/j.bmc.2009.06.001]

3. Whitby LR, Boyle KE, Cai L, Yu X, Gochin M, Boger DL..  (2012)  Discovery of HIV fusion inhibitors targeting gp41 using a comprehensive α-helix mimetic library.,  22  (8): [PMID:22424973] [10.1016/j.bmcl.2012.02.062]

4. Chong H, Qiu Z, Su Y, He Y..  (2015)  The N-Terminal T-T Motif of a Third-Generation HIV-1 Fusion Inhibitor Is Not Required for Binding Affinity and Antiviral Activity.,  58  (16): [PMID:26256053] [10.1021/acs.jmedchem.5b00109]

5. McGee TD, Yi HA, Allen WJ, Jacobs A, Rizzo RC..  (2017)  Structure-based identification of inhibitors targeting obstruction of the HIVgp41 N-heptad repeat trimer.,  27  (14): [PMID:28558972] [10.1016/j.bmcl.2017.05.020]

6. Meng G, Pu J, Li Y, Han A, Tian Y, Xu W, Zhang T, Li X, Lu L, Wang C, Jiang S, Liu K..  (2019)  Design and Biological Evaluation of m-Xylene Thioether-Stapled Short Helical Peptides Targeting the HIV-1 gp41 Hexameric Coiled-Coil Fusion Complex.,  62  (19): [PMID:31513410] [10.1021/acs.jmedchem.9b00882]

Source

Source(1):

• Scientific Literature