6-{7-[5-Ethyl-5-(5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid

ID: ALA145347

Cas Number: 25999-31-9

PubChem CID: 5360807

Product Number: L303258, Order Now?

Max Phase: Phase

Molecular Formula: C34H54O8

Molecular Weight: 590.80

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lasalocid | Lasalocid a | NSC-243048 | RO 2-2985 | RO-2-2985 | RO-22985 | lasalocid|Lasalocid A|25999-31-9|Lasalocide|Antibiotic X 537A|Lasalocido|Lasalocidum|Lasalocide A|Ionophore X 537A|X 537A|Ro 2-2985|UNII-W7V2ZZ2FWB|Lasalocide [INN-French]|Lasalocidum [INN-Latin]|W7V2ZZ2FWB|Lasalocido [INN-Spanish]|EINECS 247-401-9|X-537A|NSC 243048|Ro-22985|NSC-243048|RO-2-2985|DTXSID9048485|CHEBI:92181|NSC243048|6-(7-(5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furShow More⌵

Synonyms from Alternative Forms(1): Lasalocid A Sodium

Canonical SMILES:  CC[C@@H](C(=O)[C@@H](C)[C@@H](O)[C@H](C)CCc1ccc(C)c(O)c1C(=O)O)[C@H]1O[C@](CC)([C@H]2CC[C@](O)(CC)[C@H](C)O2)C[C@@H]1C

Standard InChI:  InChI=1S/C34H54O8/c1-9-25(31-21(6)18-34(11-3,42-31)26-16-17-33(40,10-2)23(8)41-26)30(37)22(7)28(35)19(4)12-14-24-15-13-20(5)29(36)27(24)32(38)39/h13,15,19,21-23,25-26,28,31,35-36,40H,9-12,14,16-18H2,1-8H3,(H,38,39)/t19-,21+,22+,23+,25+,26-,28+,31+,33-,34+/m1/s1

Standard InChI Key:  BBMULGJBVDDDNI-OWKLGTHSSA-N

Molfile:  

     RDKit          2D

 44 46  0  0  1  0  0  0  0  0999 V2000
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   -2.8208    1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9667   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625   -0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208    1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8333    2.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    3.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1375    0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458    1.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375    1.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208    3.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792    0.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542    0.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417    2.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667    2.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7902   -1.8264    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4924    0.5428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 17  1  0
  3  6  1  0
  4  1  1  0
  5  1  1  0
  6  4  1  0
  7  3  1  0
  8 11  1  0
  9  2  2  0
 10  2  1  0
 11  5  1  0
 12  4  1  0
 13  5  1  0
 14  7  1  0
 15 21  1  0
 16  8  1  0
 17 23  1  0
 18  3  2  0
 19 25  2  0
 20 10  2  0
 21 22  1  0
 22 11  1  0
 23 26  1  0
 24 17  2  0
 25 24  1  0
 26 27  1  0
 27 14  1  0
 28  9  1  0
 29 10  1  0
 15 30  1  1
 14 31  1  1
  5 32  1  6
  6 33  1  6
  7 34  1  6
 15 35  1  0
 12 36  1  1
 16 37  1  6
 38 19  1  0
 27 39  1  1
 40 32  1  0
 41 33  1  0
 42 35  1  0
 13 12  1  0
 16 15  1  0
  9 19  1  0
 11 43  1  6
  4 44  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA145347

   Lasalocid

2. Alternative Forms:

   

   ALA145347

   Lasalocid A sodium salt solution

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 590.80

Molecular Weight (Monoisotopic): 590.3819

AlogP: 5.84

#Rotatable Bonds: 13

Polar Surface Area: 133.52

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.64

CX Basic pKa: ┄

CX LogP: 7.67

CX LogD: 4.16

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.23

Np Likeness Score: 1.74

References

1. Bochis RJ, Chabala JC, Harris E, Peterson LH, Barash L, Beattie T, Brown JE, Graham DW, Waksmunski FS, Tischler M..  (1991)  Benzylated 1,2,3-triazoles as anticoccidiostats.,  34  (9): [PMID:1895303] [10.1021/jm00113a024]

2. McFarland JW, Gans DJ..  (1987)  Cluster significance analysis contrasted with three other quantitative structure-activity relationship methods.,  30  (1): [PMID:3806603] [10.1021/jm00384a008]

3. Brown GR, Foubister AJ..  (1983)  Anticoccidial activity of crown polyethers.,  26  (4): [PMID:6220152] [10.1021/jm00358a025]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Huczyński A, Rutkowski J, Borowicz I, Wietrzyk J, Maj E, Brzezinski B..  (2013)  One-pot synthesis and cytotoxicity studies of new Mannich base derivatives of polyether antibiotic--lasalocid acid.,  23  (18): [PMID:23932361] [10.1016/j.bmcl.2013.07.040]

6.  (2014)  Agents and methods for treating ischemic and other diseases, 

7. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

8. Abdelkafi H, Michau A, Pons V, Ngadjeua F, Clerget A, Ait Ouarab L, Buisson DA, Montoir D, Caramelle L, Gillet D, Barbier J, Cintrat JC..  (2020)  Structure-Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin.,  63  (15): [PMID:32648758] [10.1021/acs.jmedchem.0c00298]

9. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(5):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• Patent Bioactivity Data
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data