cis-(E)-ethyl 4-(5-((4R,5S,E)-5-hydroxy-4-methylhex-2-enyl)-1,3-dioxan-2-yl)-3-methylbut-2-enoate

ID: ALA2286009

PubChem CID: 76320061

Max Phase: Preclinical

Molecular Formula: C18H30O5

Molecular Weight: 326.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C(\C)C[C@H]1OC[C@H](C/C=C/[C@@H](C)[C@H](C)O)CO1

Standard InChI:  InChI=1S/C18H30O5/c1-5-21-17(20)9-13(2)10-18-22-11-16(12-23-18)8-6-7-14(3)15(4)19/h6-7,9,14-16,18-19H,5,8,10-12H2,1-4H3/b7-6+,13-9+/t14-,15+,16-,18-/m1/s1

Standard InChI Key:  ZRZIZJJZFSFUKE-GJZSMEHLSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   16.4759  -15.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4759  -16.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1812  -16.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8865  -16.4222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8865  -15.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1812  -15.1923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5954  -15.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3019  -15.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0108  -15.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2995  -16.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7688  -16.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0605  -16.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3534  -16.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6451  -16.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9380  -16.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2297  -16.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6439  -15.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9391  -17.6532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7173  -15.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7161  -16.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4274  -15.2061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0078  -16.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0067  -17.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  6
  7  8  1  0
  8  9  2  0
  8 10  1  0
  2 11  1  1
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  6
 15 18  1  1
  9 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2286009

   ethyl (E)-4-[5-[(E,4R,5S)-5-hydroxy-4-methylhex-2-enyl]-1,3-dioxan-2-yl]-3-methylbut-2-enoate

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: 326.43

Molecular Weight (Monoisotopic): 326.2093

AlogP: 2.84

#Rotatable Bonds: 8

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.73

CX LogD: 2.73

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.42

Np Likeness Score: 1.57

References

1. Clinch K.  (1996)  Synthesis of analogues of monic acids A and C: Potential herbicides and inhibitors of isoleucyl tRNA synthetase,  6  (4): [10.1016/0960-894X(96)00050-9]

Source

Source(1):

• Scientific Literature