N-[2-O-(2-deoxy-2-stearoylamino-beta-D-glucopyranosyl-(1->4)-2-acetamido-2,3-dideoxy-alpha-D-glucopyranosid-3-yl)-glycoloyl]-L-alpha-aminobutanoyl-D-isoglutamine

ID: ALA4089826

PubChem CID: 15735846

Max Phase: Preclinical

Molecular Formula: C43H77N5O16

Molecular Weight: 920.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCC(=O)N[C@H]1[C@H](O[C@H]2[C@H](OCC(=O)N[C@@H](CC)C(=O)N[C@H](CCC(=O)O)C(N)=O)[C@@H](NC(C)=O)C(O)O[C@@H]2CO)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C43H77N5O16/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-31(52)48-34-37(57)36(56)29(23-49)63-43(34)64-38-30(24-50)62-42(60)35(45-26(3)51)39(38)61-25-32(53)46-27(5-2)41(59)47-28(40(44)58)21-22-33(54)55/h27-30,34-39,42-43,49-50,56-57,60H,4-25H2,1-3H3,(H2,44,58)(H,45,51)(H,46,53)(H,47,59)(H,48,52)(H,54,55)/t27-,28+,29+,30+,34+,35+,36+,37+,38+,39+,42?,43-/m0/s1

Standard InChI Key:  YIMHNPAETXOBQK-DMLOAWKYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4089826

   (4R)-4-[[(2S)-2-[[2-[(3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(octadecanoylamino)oxan-2-yl]oxy-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxyacetyl]amino]butanoyl]amino]-5-amino-5-oxopentanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 920.11

Molecular Weight (Monoisotopic): 919.5365

AlogP: -0.11

#Rotatable Bonds: 33

Polar Surface Area: 334.86

Molecular Species: ACID

HBA: 15

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.13

CX Basic pKa: ┄

CX LogP: 0.50

CX LogD: -2.58

Aromatic Rings: ┄

Heavy Atoms: 64

QED Weighted: 0.04

Np Likeness Score: 0.68

References

1. Effenberg R, Turánek Knötigová P, Zyka D, Čelechovská H, Mašek J, Bartheldyová E, Hubatka F, Koudelka Š, Lukáč R, Kovalová A, Šaman D, Křupka M, Barkocziova L, Kosztyu P, Šebela M, Drož L, Hučko M, Kanásová M, Miller AD, Raška M, Ledvina M, Turánek J..  (2017)  Nonpyrogenic Molecular Adjuvants Based on norAbu-Muramyldipeptide and norAbu-Glucosaminyl Muramyldipeptide: Synthesis, Molecular Mechanisms of Action, and Biological Activities in Vitro and in Vivo.,  60  (18): [PMID:28829599] [10.1021/acs.jmedchem.7b00593]

Source

Source(1):

• Scientific Literature