Ethyl 2,3-dideoxy-alpha-D-glycero-hex-2-enopyranosid-4-ulose

ID: ALA4087359

PubChem CID: 11367256

Max Phase: Preclinical

Molecular Formula: C8H12O4

Molecular Weight: 172.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCO[C@@H]1C=CC(=O)[C@@H](CO)O1

Standard InChI:  InChI=1S/C8H12O4/c1-2-11-8-4-3-6(10)7(5-9)12-8/h3-4,7-9H,2,5H2,1H3/t7-,8+/m1/s1

Standard InChI Key:  DSLXQUZNOYUOKK-SFYZADRCSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
    3.6543   -4.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6543   -5.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3663   -5.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783   -5.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783   -4.3751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3663   -3.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3663   -3.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0808   -2.7209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7923   -5.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7911   -6.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5049   -6.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9386   -3.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  7  8  1  0
  4  9  1  6
  9 10  1  0
 10 11  1  0
  1 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087359

   (2S,6R)-2-ethoxy-6-(hydroxymethyl)-2H-pyran-5-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: 172.18

Molecular Weight (Monoisotopic): 172.0736

AlogP: -0.13

#Rotatable Bonds: 3

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.47

CX LogD: 0.47

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.64

Np Likeness Score: 1.53

References

1. Santos JAM, Santos CS, Almeida CLA, Silva TDS, Freitas Filho JR, Militão GCG, da Silva TG, da Cruz CHB, Freitas JCR, Menezes PH..  (2017)  Structure-based design, synthesis and antitumoral evaluation of enulosides.,  128  [PMID:28189083] [10.1016/j.ejmech.2017.01.036]

Source

Source(1):

• Scientific Literature