(2R,3S,4S,5S,6R)-2-((2R,3R,4R,5R)-4-hydroxy-2-(2-hydroxyethyl)-5-(hydroxymethyl)pyrrolidin-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA519261

PubChem CID: 10246556

Max Phase: Preclinical

Molecular Formula: C13H25NO9

Molecular Weight: 339.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCC[C@H]1N[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C13H25NO9/c15-2-1-5-12(8(18)6(3-16)14-5)23-13-11(21)10(20)9(19)7(4-17)22-13/h5-21H,1-4H2/t5-,6-,7-,8-,9-,10+,11+,12-,13+/m1/s1

Standard InChI Key:  IUJDTJSEAKUOOC-KEGYGLKMSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -1.1941   -4.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3691   -4.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135   -3.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -2.9437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4495   -3.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304   -3.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4055   -2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -2.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6816   -4.8842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718   -3.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852   -3.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127   -4.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -4.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8354   -4.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6521   -3.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1433   -4.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077   -5.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9849   -5.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938   -5.5101    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6531   -6.2173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2974   -6.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9864   -3.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8065   -3.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9634   -4.5253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  1
  5  6  1  1
  9 13  1  0
 13 14  1  0
  6  7  1  0
  2  3  1  0
  7  8  1  0
  3  4  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  1  9  1  6
 13 19  1  6
  4  5  1  0
 18 20  1  1
  3 10  1  6
 17 21  1  1
  5  1  1  0
 15 22  1  1
 10 11  1  0
 22 23  1  0
  1  2  1  0
 16 24  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA519261

   (2R,3S,4S,5S,6R)-2-((2R,3R,4R,5R)-4-hydroxy-2-(2-hydroxyethyl)-5-(hydroxymethyl)pyrrolidin-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Molecule Features

Natural Product: Yes

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: 339.34

Molecular Weight (Monoisotopic): 339.1529

AlogP: -4.75

#Rotatable Bonds: 6

Polar Surface Area: 172.10

Molecular Species: BASE

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.19

CX Basic pKa: 9.06

CX LogP: -4.60

CX LogD: -6.26

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.23

Np Likeness Score: 2.30

References

1. Yamashita T, Yasuda K, Kizu H, Kameda Y, Watson AA, Nash RJ, Fleet GW, Asano N..  (2002)  New polyhydroxylated pyrrolidine, piperidine, and pyrrolizidine alkaloids from Scilla sibirica.,  65  (12): [PMID:12502331] [10.1021/np020296h]

Source

Source(1):

• Scientific Literature