(2S,3R,4S,5R,6S)-6-((2S,3S,4R)-2-(11-(4-fluorophenyl)undecanamido)-3,4-dihydroxyoctadecyloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

ID: ALA1673367

PubChem CID: 53326929

Max Phase: Preclinical

Molecular Formula: C41H70FNO10

Molecular Weight: 756.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](CO[C@H]1O[C@H](C(=O)O)[C@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCc1ccc(F)cc1

Standard InChI:  InChI=1S/C41H70FNO10/c1-2-3-4-5-6-7-8-9-10-14-17-20-23-33(44)35(46)32(29-52-41-38(49)36(47)37(48)39(53-41)40(50)51)43-34(45)24-21-18-15-12-11-13-16-19-22-30-25-27-31(42)28-26-30/h25-28,32-33,35-39,41,44,46-49H,2-24,29H2,1H3,(H,43,45)(H,50,51)/t32-,33+,35-,36-,37+,38+,39-,41-/m0/s1

Standard InChI Key:  AQYIMPWPOQPKDH-HMOKDYLBSA-N

Molfile:  

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Alternative Forms

1. Parent:

   

   ALA1673367

   (2S,3R,4S,5R,6S)-6-[(2S,3S,4R)-2-[11-(4-fluorophenyl)undecanoylamino]-3,4-dihydroxyoctadecoxy]-3,4,5-trihydroxyoxane-2-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: 756.01

Molecular Weight (Monoisotopic): 755.4984

AlogP: 6.09

#Rotatable Bonds: 31

Polar Surface Area: 186.01

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 3.18

CX Basic pKa: ┄

CX LogP: 8.04

CX LogD: 4.60

Aromatic Rings: 1

Heavy Atoms: 53

QED Weighted: 0.04

Np Likeness Score: 0.69

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