(trans)-5-Dodecyl-2-methoxy-7-methyl-2-oxo-2,3,4,5-tetrahydro-2lambda*5*-[1,2]oxaphosphepine-6-carboxylic acid methyl ester

ID: ALA3401170

PubChem CID: 118728282

Max Phase: Preclinical

Molecular Formula: C21H39O5P

Molecular Weight: 402.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC[C@H]1CC[P@@](=O)(OC)OC(C)=C1C(=O)OC

Standard InChI:  InChI=1S/C21H39O5P/c1-5-6-7-8-9-10-11-12-13-14-15-19-16-17-27(23,25-4)26-18(2)20(19)21(22)24-3/h19H,5-17H2,1-4H3/t19-,27+/m0/s1

Standard InChI Key:  ZWCSIELZWHDDDD-UZTOHYMASA-N

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    1.6852   -0.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5574    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    1.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435   -2.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -1.6217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2896    1.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351    3.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002   -0.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    5.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246    1.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0999    2.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4962    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6715    2.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0678    2.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2431    3.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6394    2.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8147    3.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2110    2.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3863    3.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5028    3.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  6  2  0
  1  3  1  0
  3  4  1  0
  7  5  1  0
  4  5  1  0
  6  7  1  0
  8  9  1  0
  9  6  1  0
  3 10  2  0
  3 11  1  6
  2 12  1  0
  9 13  2  0
 11 14  1  0
  8 15  1  0
  7 16  1  6
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3401170

   ---

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: 402.51

Molecular Weight (Monoisotopic): 402.2535

AlogP: 6.62

#Rotatable Bonds: 13

Polar Surface Area: 61.83

Molecular Species: ┄

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.53

CX LogD: 5.53

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.20

Np Likeness Score: 0.30

References

1. Vasilieva E, Dutta S, Malla RK, Martin BP, Spilling CD, Dupureur CM..  (2015)  Rat hormone sensitive lipase inhibition by cyclipostins and their analogs.,  23  (5): [PMID:25678014] [10.1016/j.bmc.2015.01.028]

2. Cavalier JF, Spilling CD, Durand T, Camoin L, Canaan S..  (2021)  Lipolytic enzymes inhibitors: A new way for antibacterial drugs discovery.,  209  [PMID:33071055] [10.1016/j.ejmech.2020.112908]

Source

Source(1):

• Scientific Literature