5-Acetamido-4-(3-(2-(6-methoxynaphthalen-2-yl)propanoyl)guanidino-6-(1,2,3-trihydroxypropyl)-4,5-dihydro-6Hpyran-2-carboxylic acid

ID: ALA4164188

Chembl Id: CHEMBL4164188

PubChem CID: 71811523

Max Phase: Preclinical

Molecular Formula: C26H32N4O9

Molecular Weight: 544.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2cc([C@H](C)C(=O)/N=C(\N)N[C@H]3C=C(C(=O)O)O[C@@H]([C@H](O)[C@H](O)CO)[C@@H]3NC(C)=O)ccc2c1

Standard InChI:  InChI=1S/C26H32N4O9/c1-12(14-4-5-16-9-17(38-3)7-6-15(16)8-14)24(35)30-26(27)29-18-10-20(25(36)37)39-23(21(18)28-13(2)32)22(34)19(33)11-31/h4-10,12,18-19,21-23,31,33-34H,11H2,1-3H3,(H,28,32)(H,36,37)(H3,27,29,30,35)/t12-,18-,19+,21+,22+,23+/m0/s1

Standard InChI Key:  HHPRCUYASYWQIV-BNBPWJHPSA-N

Alternative Forms

1. Parent:

   

   ALA4164188

   (2R,3R,4S)-3-acetamido-4-[[amino-[[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]amino]methylidene]amino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic 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: 544.56

Molecular Weight (Monoisotopic): 544.2169

AlogP: -0.66

#Rotatable Bonds: 9

Polar Surface Area: 213.03

Molecular Species: ZWITTERION

HBA: 8

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.20

CX Basic pKa: 8.56

CX LogP: -2.58

CX LogD: -2.60

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.16

Np Likeness Score: 0.47

References

1. Hsu PH, Chiu DC, Wu KL, Lee PS, Jan JT, Cheng YE, Tsai KC, Cheng TJ, Fang JM..  (2018)  Acylguanidine derivatives of zanamivir and oseltamivir: Potential orally available prodrugs against influenza viruses.,  154  [PMID:29843102] [10.1016/j.ejmech.2018.05.030]

Source

Source(1):

• Scientific Literature