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Chemical structure of Retrocyclin-1

GA23480

Retrocyclin-1

Also known as 1-[3-[(1R,4S,7R,10S,16S,22R,25S,28R,31S,34R,37S,43S,49R,52S)-10,25,37,52-tetrakis[(2S)-butan-2-yl]-4,31,43-tris(3-carbamimidamidopropyl)-3,6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51,54-octadecaoxo-56,57,60,61,64,65-hexathia-2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53-octadecazatetracyclo[26.26.4.47,22.434,49]hexahexacontan-16-yl]propyl]guanidine

The theta-defensin retrocyclin-1, also called RC-100, is a circular octadecapeptide containing an internal trisulfide ladder· Besides its antimicrobial activity, retrocyclin-1 has a remarkable ability to protect human cells in vitro from infection by T- and M-tropic strains of HIV-1· Its effectiveness against HIV-1 results from the prevention of viral entry, and is correlated with its ability to recognize and bind with high affinity to glycoproteins and glycolipids implicated in HIV-1 entry, such as gp120 (KD = 35·4 nM), CD4 (KD = 31 nM), and galactosylceramide (KD = 24·1 nM)· Retrocyclin represents a new class of small molecule HIV-1 entry inhibitors

ChemicalCAS724760-19-4MW1918.42FormulaC74H128N30O18S6
CAS number
724760-19-4
Molecular weight
1918.42
Formula
C74H128N30O18S6
Solubility
Soluble in DMSO
InChIKey
HKPMSXLQWRKULW-QYJCGYSGSA-N
Catalogue number
GA23480
Brand
GLPBIO
Computed properties PubChem CID 16130540 · XLogP -5 · TPSA 923 Ų · H-bond donors 30
XLogP
-5
TPSA
923 Ų
H-bond donors
30
H-bond acceptors
28
Rotatable bonds
28
Heavy atoms
128

SMILES CC[C@H](C)[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)NCC(=O)N1)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@@H]3CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H]4CSSC[C@@H](C(=O)N[C@H](C(=O)N3)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)CNC4=O)CCCNC(=N)N)[C@@H](C)CC)[C@@H](C)CC)NC(=O)[C@@H](NC2=O)CCCNC(=N)N)[C@@H](C)CC

Computed descriptors from PubChem (CID 16130540), public domain. Identity cross-checked against the supplier's molecular formula and weight — verify before use.

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