(+/-)-(trans)-1-methyl-3-(pentadecyloxy)-4,5,5a,6-tetrahydrofuro[3,4-e][1,2]oxaphosphepin-8(3H)-one 3-oxide

ID: ALA3401164

PubChem CID: 118728276

Max Phase: Preclinical

Molecular Formula: C23H41O5P

Molecular Weight: 428.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H41O5P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17-27-29(25)18-16-21-19-26-23(24)22(21)20(2)28-29/h21H,3-19H2,1-2H3/t21-,29-/m1/s1

Standard InChI Key:  ZPRBDRVNNUTXRC-ONOMSOESSA-N

Molfile:  

     RDKit          2D

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    2.9655  -16.7131    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
    0.0000   -1.3541    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
    3.2603  -19.2963    0.0000 C   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
   -1.6754   -1.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0729  -15.5065    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
    2.3677  -18.0897    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
   -2.9378    0.5738    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
    2.6707  -14.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0811   -8.9634    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
   -4.3608    0.9869    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
   -2.0994    2.7431    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
   -4.7748    2.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7824  -20.3970    0.0000 C   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
   -3.0072   -1.9084    0.0000 H   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
  6  7  1  0
 22 26  2  0
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 23 18  1  0
  4 23  1  0
  3  4  1  0
  7 17  1  0
 15 22  1  0
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  1 30  1  0
  8 27  1  0
 25  5  1  0
 28 19  1  0
 16 11  1  0
 11 10  1  0
 12  2  1  0
 11 29  1  1
 14  8  1  0
 11  9  1  0
  9 15  1  0
 25 28  1  6
 25 21  2  0
 19  6  1  0
 30 16  2  0
 17 13  1  0
  5 10  1  0
 30 24  1  0
 18 12  1  0
  1 25  1  0
  2 14  1  0
 22 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3401164

   ---

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: 428.55

Molecular Weight (Monoisotopic): 428.2692

AlogP: 7.15

#Rotatable Bonds: 15

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.97

CX LogD: 5.97

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.16

Np Likeness Score: 0.45

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]

Source

Source(1):

• Scientific Literature