(S)-(3-(isopropyldisulfanyl)-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: ALA1923805

PubChem CID: 54768119

Max Phase: Preclinical

Molecular Formula: C31H41NO11S2

Molecular Weight: 667.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2cc([C@H](C)C(=O)OCC/C(SSC(C)C)=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/C31H41NO11S2/c1-17(2)44-45-25(10-11-41-30(38)18(3)20-6-7-22-13-23(40-5)9-8-21(22)12-20)19(4)32(16-33)14-26(34)42-15-24-27(35)28(36)29(37)31(39)43-24/h6-9,12-13,16-18,24,27-29,31,35-37,39H,10-11,14-15H2,1-5H3/b25-19-/t18-,24+,27+,28-,29+,31-/m0/s1

Standard InChI Key:  WBHVZXPXXOFAPN-OTYNLLNUSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1923805

   [(Z)-4-[formyl-[2-oxo-2-[[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]ethyl]amino]-3-(propan-2-yldisulfanyl)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: 667.80

Molecular Weight (Monoisotopic): 667.2121

AlogP: 2.71

#Rotatable Bonds: 15

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: 1.28

CX LogD: 1.28

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.12

Np Likeness Score: 0.77

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