(3S,7R,8aS)-7-hydroxy-3-(hydroxymethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

ID: ALA2229108

Chembl Id: CHEMBL2229108

Cas Number: 211868-63-2

PubChem CID: 9815587

Max Phase: Preclinical

Molecular Formula: C8H12N2O4

Molecular Weight: 200.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N[C@@H](CO)C(=O)N2C[C@H](O)C[C@@H]12

Standard InChI:  InChI=1S/C8H12N2O4/c11-3-5-8(14)10-2-4(12)1-6(10)7(13)9-5/h4-6,11-12H,1-3H2,(H,9,13)/t4-,5+,6+/m1/s1

Standard InChI Key:  FUYZNZHRVJWTLT-SRQIZXRXSA-N

Alternative Forms

1. Parent:

   

   ALA2229108

   Cyclo-trans-4-L-Hydroxyprolyl-L-serine

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: 200.19

Molecular Weight (Monoisotopic): 200.0797

AlogP: -2.56

#Rotatable Bonds: 1

Polar Surface Area: 89.87

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.58

CX Basic pKa:

CX LogP: -2.99

CX LogD: -3.00

Aromatic Rings: 0

Heavy Atoms: 14

QED Weighted: 0.43

Np Likeness Score: 1.67

References

1. Li XJ, Zhang Q, Zhang AL, Gao JM..  (2012)  Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities.,  60  (13): [PMID:22409377] [10.1021/jf300146n]

2. Jiang Q, Zhang J, Tong P, Gao Y, Lv Y, Wang C, Luo M, Sun M, Wang J, Feng Y, Cao L, Wang G, Wang Y, Kan Q, Zhang T, Wang Y, Liu K, Sun J, He Z..  (2019)  Bioactivatable Pseudotripeptidization of Cyclic Dipeptides To Increase the Affinity toward Oligopeptide Transporter 1 for Enhanced Oral Absorption: An Application to Cyclo(l-Hyp-l-Ser) (JBP485).,  62  (17): [PMID:31393124] [10.1021/acs.jmedchem.9b00358]

3. Wu B, Zheng X, Li X, Wang C, Li L, Tang Z, Cui H, Li Z, Chen L, Ma X..  (2022)  Design, synthesis and activity evaluation of prodrug form JBP485 and Vitamin E for alleviation of NASH.,  56  [PMID:34808388] [10.1016/j.bmcl.2021.128464]

Source

Source(1):

• Scientific Literature