(2S,3S)-3-hydroxy-1,2,3,6-tetrahydropyridine-2-carboxylic acid

ID: ALA403603

Chembl Id: CHEMBL403603

PubChem CID: 24882573

Max Phase: Preclinical

Molecular Formula: C6H9NO3

Molecular Weight: 143.14

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (2S,3S)-3-Hydroxybaikiain | (2S,3S)-3-Hydroxybaikiain|CHEMBL403603|BDBM50235890|AKOS006358861|(2S,3S)-3-hydroxy-1,2,3,6-tetrahydropyridine-2-carboxylic acid

Canonical SMILES:  O=C(O)[C@H]1NCC=C[C@@H]1O

Standard InChI:  InChI=1S/C6H9NO3/c8-4-2-1-3-7-5(4)6(9)10/h1-2,4-5,7-8H,3H2,(H,9,10)/t4-,5-/m0/s1

Standard InChI Key:  SBTHNGLUOHGTIG-WHFBIAKZSA-N

Alternative Forms

1. Parent:

   

   ALA403603

   (2S,3S)-3-Hydroxybaikiain

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: 143.14

Molecular Weight (Monoisotopic): 143.0582

AlogP: -1.04

#Rotatable Bonds: 1

Polar Surface Area: 69.56

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.66

CX Basic pKa: 9.30

CX LogP: -3.25

CX LogD: -3.25

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.41

Np Likeness Score: 1.87

References

1. Ohara C, Takahashi R, Miyagawa T, Yoshimura Y, Kato A, Adachi I, Takahata H..  (2008)  Synthesis of all stereoisomers of 3-hydroxypipecolic acid and 3-hydroxy-4,5-dehydropipecolic acid and their evaluation as glycosidase inhibitors.,  18  (6): [PMID:18296050] [10.1016/j.bmcl.2008.02.028]

2. Yoshimura Y, Ohara C, Imahori T, Saito Y, Kato A, Miyauchi S, Adachi I, Takahata H..  (2008)  Synthesis of both enantiomers of hydroxypipecolic acid derivatives equivalent to 5-azapyranuronic acids and evaluation of their inhibitory activities against glycosidases.,  16  (17): [PMID:18703340] [10.1016/j.bmc.2008.06.016]

Source

Source(1):

• Scientific Literature