Glucopiericidin A

ID: ALA4092369

Chembl Id: CHEMBL4092369

Cas Number: 108073-65-0

PubChem CID: 44608046

Max Phase: Preclinical

Molecular Formula: C31H47NO9

Molecular Weight: 577.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(\C)[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](C)/C=C(C)/C=C/C/C(C)=C/Cc1nc(OC)c(OC)c(O)c1C

Standard InChI:  InChI=1S/C31H47NO9/c1-9-19(4)28(41-31-27(37)26(36)25(35)23(16-33)40-31)20(5)15-18(3)12-10-11-17(2)13-14-22-21(6)24(34)29(38-7)30(32-22)39-8/h9-10,12-13,15,20,23,25-28,31,33,35-37H,11,14,16H2,1-8H3,(H,32,34)/b12-10+,17-13+,18-15+,19-9+/t20-,23-,25-,26+,27-,28+,31+/m1/s1

Standard InChI Key:  YQOARHMNLCWEPG-DFTUVXBYSA-N

Alternative Forms

1. Parent:

   

   ALA4092369

   Glucopiericidin A

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: 577.72

Molecular Weight (Monoisotopic): 577.3251

AlogP: 3.28

#Rotatable Bonds: 13

Polar Surface Area: 150.96

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.88

CX Basic pKa: 2.94

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.17

Np Likeness Score: 1.98

References

1. Granchi C, Fortunato S, Minutolo F..  (2016)  Anticancer agents interacting with membrane glucose transporters.,  7  (9): [PMID:28042452] [10.1039/C6MD00287K]

2. Zhou X, Liang Z, Li K, Fang W, Tian Y, Luo X, Chen Y, Zhan Z, Zhang T, Liao S, Liu S, Liu Y, Fenical W, Tang L..  (2019)  Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1.,  62  (15): [PMID:31298537] [10.1021/acs.jmedchem.9b00598]

3. Liang Z, Chen Y, Gu T, She J, Dai F, Jiang H, Zhan Z, Li K, Liu Y, Zhou X, Tang L..  (2021)  LXR-Mediated Regulation of Marine-Derived Piericidins Aggravates High-Cholesterol Diet-Induced Cholesterol Metabolism Disorder in Mice.,  64  (14.0): [PMID:34251816] [10.1021/acs.jmedchem.1c00175]

4. Govindarajan M..  (2018)  Amphiphilic glycoconjugates as potential anti-cancer chemotherapeutics.,  143  [PMID:29126728] [10.1016/j.ejmech.2017.10.015]

Source

Source(1):

• Scientific Literature