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

ID: ALA1673368

PubChem CID: 53317752

Max Phase: Preclinical

Molecular Formula: C47H74FNO11

Molecular Weight: 848.10

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

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(Oc2ccc(F)cc2)cc1

Standard InChI: InChI=1S/C47H74FNO11/c1-2-3-4-5-6-7-8-9-10-14-17-20-23-39(50)41(52)38(33-58-47-44(55)42(53)43(54)45(60-47)46(56)57)49-40(51)24-21-18-15-12-11-13-16-19-22-34-25-29-36(30-26-34)59-37-31-27-35(48)28-32-37/h25-32,38-39,41-45,47,50,52-55H,2-24,33H2,1H3,(H,49,51)(H,56,57)/t38-,39+,41-,42-,43+,44+,45-,47-/m0/s1

Standard InChI Key: RCVSSFRMAADHPW-QDRYOOTBSA-N

Molfile:

     RDKit          2D

 60 62  0  0  0  0  0  0  0  0999 V2000
   15.0458  -22.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0458  -23.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7579  -23.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4699  -23.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4699  -22.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7579  -21.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1855  -21.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1837  -23.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7579  -24.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3320  -23.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3302  -21.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3277  -21.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8988  -22.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6145  -22.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6169  -21.1771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9036  -20.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9061  -19.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1880  -21.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3277  -22.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3253  -23.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0434  -22.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7567  -22.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4724  -22.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1856  -22.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9013  -22.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6145  -22.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3302  -22.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0435  -22.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7592  -22.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4724  -22.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1881  -22.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9014  -22.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6170  -22.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3303  -22.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0460  -22.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6217  -19.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3350  -19.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0507  -19.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7639  -19.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4796  -19.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1929  -19.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9085  -19.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6218  -19.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3375  -19.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0507  -19.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6169  -22.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0448  -20.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7572  -21.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4739  -20.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4737  -19.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7606  -19.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1877  -21.2021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0458  -21.1813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9028  -20.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6141  -21.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3287  -20.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3305  -19.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6116  -19.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8999  -19.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0450  -19.5557    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  0
 14 15  1  6
 30 31  1  0
  1  2  1  0
 31 32  1  0
 15 16  1  0
 32 33  1  0
  4  8  1  6
 33 34  1  0
 16 17  1  0
 34 35  1  0
  1  6  1  0
 17 36  1  0
 16 18  2  0
 36 37  1  0
  3  9  1  1
 37 38  1  0
 14 19  1  0
 38 39  1  0
  2  3  1  0
 39 40  1  0
 19 20  1  1
 40 41  1  0
  2 10  1  1
 41 42  1  0
 19 21  1  0
 42 43  1  0
  3  4  1  0
 43 44  1  0
 21 22  1  0
 44 45  1  0
  1 11  1  1
 11 46  2  0
 22 23  1  0
 45 47  2  0
  4  5  1  0
 47 48  1  0
 23 24  1  0
 48 49  2  0
 11 12  1  0
 49 50  1  0
 24 25  1  0
 50 51  2  0
 51 45  1  0
  5  6  1  0
 49 52  1  0
 25 26  1  0
 21 53  1  6
  7 13  1  0
 52 54  1  0
 26 27  1  0
 54 55  2  0
 55 56  1  0
 27 28  1  0
 56 57  2  0
 13 14  1  0
 57 58  1  0
 28 29  1  0
 58 59  2  0
 59 54  1  0
  5  7  1  6
 57 60  1  0
M  END

Associated Targets(non-human)

Japanese encephalitis virus (187 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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: 848.10	Molecular Weight (Monoisotopic): 847.5246	AlogP: 7.88	#Rotatable Bonds: 33
Polar Surface Area: 195.24	Molecular Species: ACID	HBA: 10	HBD: 7
#RO5 Violations: 3	HBA (Lipinski): 12	HBD (Lipinski): 7	#RO5 Violations (Lipinski): 4
CX Acidic pKa: 3.18	CX Basic pKa: ┄	CX LogP: 9.54	CX LogD: 6.10
Aromatic Rings: 2	Heavy Atoms: 60	QED Weighted: 0.03	Np Likeness Score: 0.57

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]

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

Names and Identifiers

Alternative Forms

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source