N-((2S,3S,4R)-3,4-dihydroxy-1-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)octadecan-2-yl)-8-(4-fluorophenyl)octanamide

ID: ALA1231634

PubChem CID: 25105144

Max Phase: Preclinical

Molecular Formula: C38H66FNO9

Molecular Weight: 699.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCc1ccc(F)cc1

Standard InChI:  InChI=1S/C38H66FNO9/c1-2-3-4-5-6-7-8-9-10-11-14-17-20-31(42)34(44)30(27-48-38-37(47)36(46)35(45)32(26-41)49-38)40-33(43)21-18-15-12-13-16-19-28-22-24-29(39)25-23-28/h22-25,30-32,34-38,41-42,44-47H,2-21,26-27H2,1H3,(H,40,43)/t30-,31+,32+,34-,35-,36-,37+,38-/m0/s1

Standard InChI Key:  FBUHIWMNUBFIJZ-ZORUMLJWSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1231634

   8-(4-fluorophenyl)-N-{(1S,2S,3R)-1-[(alpha-D-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl}octanamide

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: 699.94

Molecular Weight (Monoisotopic): 699.4722

AlogP: 4.82

#Rotatable Bonds: 28

Polar Surface Area: 168.94

Molecular Species: NEUTRAL

HBA: 9

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.16

CX Basic pKa: ┄

CX LogP: 6.39

CX LogD: 6.39

Aromatic Rings: 1

Heavy Atoms: 49

QED Weighted: 0.06

Np Likeness Score: 0.84

References

1. Lin KH, Liang JJ, Huang WI, Lin-Chu SY, Su CY, Lee YL, Jan JT, Lin YL, Cheng YS, Wong CH..  (2010)  In vivo protection provided by a synthetic new alpha-galactosyl ceramide analog against bacterial and viral infections in murine models.,  54  (10): [PMID:20660669] [10.1128/aac.00368-10]

Source

Source(1):

• Scientific Literature