Pyrrolidine-3,4-diol

ID: ALA2207396

Cas Number: 131565-87-2

PubChem CID: 13329882

Max Phase: Preclinical

Molecular Formula: C4H9NO2

Molecular Weight: 103.12

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pyrrolidine-3,4-Diol | 131565-87-2|(3R,4S)-pyrrolidine-3,4-diol|cis-Pyrrolidine-3,4-diol|(3S,4R)-Pyrrolidine-3,4-diol|CIS-3,4-DIHYDROXYPYRROLIDINE|3,4-Pyrrolidinediol, (3R,4S)-rel-|CHEMBL2207396|SCHEMBL48795|DTXSID90537032|JCZPOYAMKJFOLA-ZXZARUISSA-N|AMY16905|BDBM50402978|MFCD09910269|AKOS006310246|BS-12763|CS-0183119|EN300-98790|F90176

Canonical SMILES:  O[C@@H]1CNC[C@@H]1O

Standard InChI:  InChI=1S/C4H9NO2/c6-3-1-5-2-4(3)7/h3-7H,1-2H2/t3-,4+

Standard InChI Key:  JCZPOYAMKJFOLA-ZXZARUISSA-N

Molfile:  

     RDKit          2D

  7  7  0  0  0  0  0  0  0  0999 V2000
   18.2217  -12.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0389  -12.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2932  -11.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6303  -10.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9715  -11.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7405  -12.8276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5184  -12.8288    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  5  1  0
  5  1  1  0
  1  6  1  1
  2  7  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2207396

   (3R,4S)-pyrrolidine-3,4-diol

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: 103.12

Molecular Weight (Monoisotopic): 103.0633

AlogP: -1.69

#Rotatable Bonds: ┄

Polar Surface Area: 52.49

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.51

CX Basic pKa: 9.86

CX LogP: -1.63

CX LogD: -4.02

Aromatic Rings: ┄

Heavy Atoms: 7

QED Weighted: 0.34

Np Likeness Score: 1.21

References

1. Popowycz F, Gerber-Lemaire S, Demange R, Rodriguez-García E, Asenjo AT, Robina I, Vogel P..  (2001)  Derivatives of (2R,3R,4S)-2-aminomethylpyrrolidine-3,4-diol are selective alpha-mannosidase inhibitors.,  11  (18): [PMID:11549453] [10.1016/s0960-894x(01)00477-2]

2. Robina I, Moreno-Vargas AJ, Fernández-Bolaños JG, Fuentes J, Demange R, Vogel P..  (2001)  New leads for selective inhibitors of alpha-L-fucosidases. Synthesis and glycosidase inhibitory activities of [(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives.,  11  (18): [PMID:11549468] [10.1016/s0960-894x(01)00497-8]

3. Moorthy NS, Brás NF, Ramos MJ, Fernandes PA..  (2012)  Virtual screening and QSAR study of some pyrrolidine derivatives as α-mannosidase inhibitors for binding feature analysis.,  20  (24): [PMID:23151473] [10.1016/j.bmc.2012.10.011]

Source

Source(1):

• Scientific Literature