(S)-(3-(benzyldisulfanyl)-4-(N-(2-oxo-2-(((2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methoxy)ethyl)formamido)pent-3-enyl)2-(6-methoxynaphthalen-2-yl)propanoate

ID: ALA1923804

PubChem CID: 54768120

Max Phase: Preclinical

Molecular Formula: C35H41NO11S2

Molecular Weight: 715.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2cc([C@H](C)C(=O)OCC/C(SSCc3ccccc3)=C(\C)N(C=O)CC(=O)OC[C@H]3O[C@H](O)[C@H](O)[C@@H](O)[C@@H]3O)ccc2c1

Standard InChI:  InChI=1S/C35H41NO11S2/c1-21(24-9-10-26-16-27(44-3)12-11-25(26)15-24)34(42)45-14-13-29(49-48-19-23-7-5-4-6-8-23)22(2)36(20-37)17-30(38)46-18-28-31(39)32(40)33(41)35(43)47-28/h4-12,15-16,20-21,28,31-33,35,39-41,43H,13-14,17-19H2,1-3H3/b29-22-/t21-,28+,31+,32-,33+,35-/m0/s1

Standard InChI Key:  FPUGMSTXRCRLPT-YZNZLNFISA-N

Molfile:  

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Alternative Forms

1. Parent:

   

   ALA1923804

   [(Z)-3-(benzyldisulfanyl)-4-[formyl-[2-oxo-2-[[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]ethyl]amino]pent-3-enyl] (2S)-2-(6-methoxynaphthalen-2-yl)propanoate

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: 715.84

Molecular Weight (Monoisotopic): 715.2121

AlogP: 3.50

#Rotatable Bonds: 16

Polar Surface Area: 172.29

Molecular Species: NEUTRAL

HBA: 13

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.30

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 49

QED Weighted: 0.10

Np Likeness Score: 0.65

References

1. Fan W, Wu Y, Li XK, Yao N, Li X, Yu YG, Hai L..  (2011)  Design, synthesis and biological evaluation of brain-specific glucosyl thiamine disulfide prodrugs of naproxen.,  46  (9): [PMID:21641697] [10.1016/j.ejmech.2011.05.029]

Source

Source(1):

• Scientific Literature