(E)-6-(3-Acetyl-2-hydroxy-6-methoxy-phenyl)-4-methyl-hex-4-enoic acid

ID: ALA149585

PubChem CID: 10803564

Max Phase: Preclinical

Molecular Formula: C16H20O5

Molecular Weight: 292.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(C)=O)c(O)c1C/C=C(\C)CCC(=O)O

Standard InChI:  InChI=1S/C16H20O5/c1-10(5-9-15(18)19)4-6-13-14(21-3)8-7-12(11(2)17)16(13)20/h4,7-8,20H,5-6,9H2,1-3H3,(H,18,19)/b10-4+

Standard InChI Key:  XRQADDIEKPCGSN-ONNFQVAWSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    2.0500   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2333   -0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208    0.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -0.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2333   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    0.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -2.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6  2  1  0
  7  4  1  0
  8  3  2  0
  9 15  1  0
 10  7  2  0
 11  8  1  0
 12  9  2  0
 13  6  2  0
 14  1  1  0
 15 16  1  0
 16 10  1  0
 17  9  1  0
 18  8  1  0
 19  6  1  0
 20 10  1  0
 21 18  1  0
  5 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA149585

   (E)-6-(3-acetyl-2-hydroxy-6-methoxyphenyl)-4-methylhex-4-enoic acid

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: 292.33

Molecular Weight (Monoisotopic): 292.1311

AlogP: 2.96

#Rotatable Bonds: 7

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: -0.28

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.60

Np Likeness Score: 1.37

References

1. Anderson WK, Boehm TL, Makara GM, Swann RT..  (1996)  Synthesis and modeling studies with monocyclic analogues of mycophenolic acid.,  39  (1): [PMID:8568826] [10.1021/jm9501339]

Source

Source(1):

• Scientific Literature