methyl 7-((1R,2S,3R)-3-hydroxy-2-(4-(1-hydroxycyclobutyl)phenyl)-5-oxocyclopentyl)hept-5-enoate

ID: ALA3978583

PubChem CID: 11955154

Max Phase: Preclinical

Molecular Formula: C23H30O5

Molecular Weight: 386.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc(C2(O)CCC2)cc1

Standard InChI:  InChI=1S/C23H30O5/c1-28-21(26)8-5-3-2-4-7-18-19(24)15-20(25)22(18)16-9-11-17(12-10-16)23(27)13-6-14-23/h2,4,9-12,18,20,22,25,27H,3,5-8,13-15H2,1H3/b4-2-/t18-,20+,22+/m0/s1

Standard InChI Key:  AETUZWCDUUSBRC-NEXMAASUSA-N

Molfile:  

     RDKit          2D

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    4.1421  -13.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5465  -13.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564  -13.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172  -10.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9344  -10.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1888   -9.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258   -8.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671   -9.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5246   -8.0729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360  -10.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4140  -10.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776  -11.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565  -12.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219  -10.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9663   -9.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5729   -9.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3504   -9.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5214   -8.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2990   -8.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4700   -7.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2475   -7.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8541   -7.8635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4185   -6.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7028  -11.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3722  -12.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1961   -6.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6656  -12.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  2  0
  5 11  1  6
  6 12  1  1
 12 13  2  0
 13 14  1  0
 14 26  2  0
 25 15  2  0
 15 12  1  0
  7 16  1  6
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 25 26  1  0
 24 27  1  0
 26  1  1  0
  1 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3978583

   methyl (Z)-7-[(1R,2S,3R)-3-hydroxy-2-[4-(1-hydroxycyclobutyl)phenyl]-5-oxocyclopentyl]hept-5-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: 386.49

Molecular Weight (Monoisotopic): 386.2093

AlogP: 3.38

#Rotatable Bonds: 8

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: 1.46

References

1.  (2010)  Therapeutic compounds, 

Source

Source(1):

• Patent Bioactivity Data