(3R,9S,10R,E)-3,9-Dihydroxy-10-propyl-3,4,5,8,9,10-hexahydro-2H-oxecin-2-one

ID: ALA3099274

PubChem CID: 72946877

Max Phase: Preclinical

Molecular Formula: C12H20O4

Molecular Weight: 228.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@H]1OC(=O)[C@H](O)CC/C=C/C[C@@H]1O

Standard InChI:  InChI=1S/C12H20O4/c1-2-6-11-9(13)7-4-3-5-8-10(14)12(15)16-11/h3-4,9-11,13-14H,2,5-8H2,1H3/b4-3+/t9-,10+,11+/m0/s1

Standard InChI Key:  DXOFARPHUWMJSP-BJPDOBEOSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    3.7764   -3.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7764   -4.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4817   -4.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4817   -3.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1870   -3.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1880   -4.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8923   -4.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6001   -4.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5991   -3.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8902   -3.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -5.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -4.8175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3078   -4.8147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4814   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736   -6.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -6.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  2  0
  2 12  1  1
  8 13  1  1
  3 14  1  6
 14 15  1  0
 15 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3099274

   (2R,3S,5E,9R)-3,9-dihydroxy-2-propyl-2,3,4,7,8,9-hexahydrooxecin-10-one

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: 228.29

Molecular Weight (Monoisotopic): 228.1362

AlogP: 1.16

#Rotatable Bonds: 2

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 1.45

CX LogD: 1.45

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.55

Np Likeness Score: 2.06

References

1. Jangili P, Kashanna J, Kumar CG, Poornachandra Y, Das B..  (2014)  Stereoselective total synthesis of a novel regiomer of herbarumin I and its cytotoxic and antimicrobial activities.,  24  (1): [PMID:24300737] [10.1016/j.bmcl.2013.11.010]

Source

Source(1):

• Scientific Literature