(2R,3R,4S,5S,6R)-2-[(1R,2R)-10-(4-hydroxy-5,6-dimethoxy-3-methyl-2-pyridyl)-1-[3-hydroxy-1-methyl-prop-1-enyl]-2,4,8-trimethyl-deca-3,5,8-trienoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

ID: ALA4464303

PubChem CID: 101428705

Max Phase: Preclinical

Molecular Formula: C31H47NO10

Molecular Weight: 593.71

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1nc(C/C=C(\C)C/C=C/C(C)=C/[C@@H](C)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)/C(C)=C/CO)c(C)c(O)c1OC

Standard InChI:  InChI=1S/C31H47NO10/c1-17(11-12-22-21(5)24(35)29(39-6)30(32-22)40-7)9-8-10-18(2)15-20(4)28(19(3)13-14-33)42-31-27(38)26(37)25(36)23(16-34)41-31/h8,10-11,13,15,20,23,25-28,31,33-34,36-38H,9,12,14,16H2,1-7H3,(H,32,35)/b10-8+,17-11+,18-15+,19-13+/t20-,23-,25-,26+,27-,28+,31+/m1/s1

Standard InChI Key:  ZNDBGWYPOYJCKZ-FJCIJDQSSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4464303

   2-[(2E,5E,7E,9R,10R,11E)-13-hydroxy-3,7,9,11-tetramethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytrideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-1H-pyridin-4-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 593.71

Molecular Weight (Monoisotopic): 593.3200

AlogP: 2.25

#Rotatable Bonds: 14

Polar Surface Area: 171.19

Molecular Species: NEUTRAL

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 10.88

CX Basic pKa: 2.94

CX LogP: 2.33

CX LogD: 2.33

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.14

Np Likeness Score: 2.01

References

1. 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]

2. 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]

3. 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