trans-cyclipostin P

ID: ALA3401162

PubChem CID: 118728275

Max Phase: Preclinical

Molecular Formula: C23H41O6P

Molecular Weight: 444.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCO[P@]1(=O)OC[C@@H]2COC(=O)C2=C(C)O1

Standard InChI:  InChI=1S/C23H41O6P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27-30(25)28-19-21-18-26-23(24)22(21)20(2)29-30/h21H,3-19H2,1-2H3/t21-,30+/m0/s1

Standard InChI Key:  LXXPVFWDVXTYTB-URAOTHONSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    0.0000   -1.3541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754   -1.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3672    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3213    1.2853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7902    1.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689   -0.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9378    0.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3608    0.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1640   -0.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2919   -1.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040    1.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1967   -1.2138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556    1.5498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9001   -2.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458   -2.5696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989   -2.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4915   -3.7970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8937   -5.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863   -6.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1885   -7.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811   -8.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4833  -10.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3759  -11.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781  -12.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707  -14.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0729  -15.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9655  -16.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3677  -18.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2603  -19.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625  -20.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3762  -21.6376    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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
  3 11  2  0
  3 12  1  1
  7 13  1  6
  2 14  1  0
 10 15  2  0
 12 16  1  0
 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
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3401162

   ---

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 444.55

Molecular Weight (Monoisotopic): 444.2641

AlogP: 7.09

#Rotatable Bonds: 16

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.57

CX LogD: 6.57

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.14

Np Likeness Score: 0.46

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