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Nangibotide

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Synopsis

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Chemistry

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Also known as: Dtxsid201336482, 2014384-91-7

Molecular Formula

C₅₄H₈₃N₁₅O₂₁S₂

Molecular Weight

1342.5 g/mol

InChI Key

JLOOQDWHNKOITN-DAHMAOPXSA-N

Nangibotide is a synthetic and inhibitory triggering receptor expressed on myeloid cells-1 (TREM-1) peptide, with potential anti-inflammatory and immunomodulatory activities. Upon administration, nangibotide binds to TREM-1 ligand and inhibits the binding of the TREM-1 ligand to TREM-1. This blocks the TREM-1-mediated amplification of innate immunity signaling, and prevents the production of pro-inflammatory mediators and inflammation. TREM-1, an immune-receptor expressed in neutrophils, mature monocytes, macrophages, natural killer (NK) cells and endothelial cells, is up-regulated following Toll-Like Receptors (TLR) or NOD-like receptors (NLR) signaling. It plays a key role in the amplification of inflammatory and innate immune responses.

1 2D Structure

Nangibotide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4S)-4-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-4-carboxybutanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]acetyl]amino]-5-[[(2S)-1-[[2-[[(2R)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

2.1.2 InChI

InChI=1S/C54H83N15O21S2/c1-25(2)19-29(55)47(83)65-32(9-13-38(56)71)50(86)66-33(10-14-39(57)72)51(87)67-34(12-16-43(77)78)52(88)69-36(21-44(79)80)53(89)61-26(3)46(82)59-22-40(73)62-31(11-15-42(75)76)49(85)68-35(20-27-5-7-28(70)8-6-27)48(84)60-23-41(74)63-37(24-91)54(90)64-30(45(58)81)17-18-92-4/h5-8,25-26,29-37,70,91H,9-24,55H2,1-4H3,(H2,56,71)(H2,57,72)(H2,58,81)(H,59,82)(H,60,84)(H,61,89)(H,62,73)(H,63,74)(H,64,90)(H,65,83)(H,66,86)(H,67,87)(H,68,85)(H,69,88)(H,75,76)(H,77,78)(H,79,80)/t26-,29-,30-,31-,32-,33-,34-,35-,36-,37-/m0/s1

2.1.3 InChI Key

JLOOQDWHNKOITN-DAHMAOPXSA-N

2.1.4 Canonical SMILES

CC(C)CC(C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(CC(=O)O)C(=O)NC(C)C(=O)NCC(=O)NC(CCC(=O)O)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NCC(=O)NC(CS)C(=O)NC(CCSC)C(=O)N)N

2.1.5 Isomeric SMILES

C[C@@H](C(=O)NCC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)NCC(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(C)C)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Lissamine-rhodamine Dodecanoic Acid

2. Lr-12

3. Motrem

2.2.2 Depositor-Supplied Synonyms

1. Dtxsid201336482

2. 2014384-91-7

2.3 Create Date

2022-10-11

3 Chemical and Physical Properties

Molecular Formula	C₅₄H₈₃N₁₅O₂₁S₂
Molecular Weight	1342.5 g/mol
XLogP3	-8.3
Hydrogen Bond Donor Count	20
Hydrogen Bond Acceptor Count	24
Rotatable Bond Count	45
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	634
Heavy Atom Count	92
Formal Charge	0
Complexity	2630
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

4.2 Mechanism of Action

Nangibotide targets the immunoreceptor TREM-1 (triggering receptor expressed on myeloid cells-1), and has been explored in treating inflammatory disorders like septic schock. Safety and pharmacokinetics studies have shown Nangibotide to be safe and well-tolerated in humans, while animal septic shock models have shown its ability to restore vascular function and improve survival. As of July 2020, Inotrem is recuriting patients to study Nangibotide's effects on patients with COVID-19 and systemic inflammation (NCT04429334).

Drugs in Development