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

ID: ALA3401167

PubChem CID: 118728279

Max Phase: Preclinical

Molecular Formula: C24H43O5P

Molecular Weight: 442.58

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H43O5P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-28-30(26)19-17-22-20-27-24(25)23(22)21(2)29-30/h22H,3-20H2,1-2H3/t22-,30+/m0/s1

Standard InChI Key:  SKWYYGFUDVULTB-SMSORMJASA-N

Molfile:  

     RDKit          2D

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   -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 C   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
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  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  1
  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
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 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3401167

   ---

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: 442.58

Molecular Weight (Monoisotopic): 442.2848

AlogP: 7.54

#Rotatable Bonds: 16

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: 6.40

CX LogD: 6.40

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.14

Np Likeness Score: 0.43

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