(2S,3R,4R,5S)-3,4,5-trihydroxypipecolic acid

ID: ALA442895

Chembl Id: CHEMBL442895

Cas Number: 96861-04-0

PubChem CID: 9815382

Max Phase: Preclinical

Molecular Formula: C6H11NO5

Molecular Weight: 177.16

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (2S,3R,4R,5S)-3,4,5-Trihydroxypipecolic Acid | 96861-04-0|(2S,3R,4R,5S)-3,4,5-TRIHYDROXYPIPERIDINE-2-CARBOXYLIC ACID|CHEMBL442895|(2S,3R,4R,5S)-3,4,5-trihydroxypipecolic acid|(2S,3R,4R,5S)-3,4,5-Trihydroxy-2-piperidinecarboxylic Acid|(2~{S},3~{R},4~{R},5~{S})-3,4,5-tris(oxidanyl)piperidine-2-carboxylic acid|starbld0006123|SCHEMBL942167|DTXSID00431138|BDBM50511225|2,6-dideoxy-2,6-imino-l-gulonic acid|CN0

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

Standard InChI:  InChI=1S/C6H11NO5/c8-2-1-7-3(6(11)12)5(10)4(2)9/h2-5,7-10H,1H2,(H,11,12)/t2-,3-,4+,5+/m0/s1

Standard InChI Key:  ZHFMVVUVCALAMY-QMKXCQHVSA-N

Alternative Forms

1. Parent:

   

   ALA442895

   (2S,3R,4R,5S)-3,4,5-Trihydroxypiperidine-2-carboxylic acid

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: 177.16

Molecular Weight (Monoisotopic): 177.0637

AlogP: -2.87

#Rotatable Bonds: 1

Polar Surface Area: 110.02

Molecular Species: ZWITTERION

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.36

CX Basic pKa: 8.63

CX LogP: -5.04

CX LogD: -5.06

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.29

Np Likeness Score: 1.55

References

1. 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]

2. Dashnyam P, Lin HY, Chen CY, Gao S, Yeh LF, Hsieh WC, Tu Z, Lin CH..  (2020)  Substituent Position of Iminocyclitols Determines the Potency and Selectivity for Gut Microbial Xenobiotic-Reactivating Enzymes.,  63  (9): [PMID:32105467] [10.1021/acs.jmedchem.9b01918]

3. Awolade P, Cele N, Kerru N, Gummidi L, Oluwakemi E, Singh P..  (2020)  Therapeutic significance of β-glucuronidase activity and its inhibitors: A review.,  187  [PMID:31835168] [10.1016/j.ejmech.2019.111921]

Source

Source(1):

• Scientific Literature