11-Demethylpiericidin A

ID: ALA4517191

PubChem CID: 155541032

Max Phase: Preclinical

Molecular Formula: C24H35NO4

Molecular Weight: 401.55

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H35NO4/c1-8-10-21(26)18(4)15-17(3)12-9-11-16(2)13-14-20-19(5)22(27)23(28-6)24(25-20)29-7/h8-10,12-13,15,18,21,26H,11,14H2,1-7H3,(H,25,27)/b10-8+,12-9+,16-13+,17-15+/t18-,21+/m1/s1

Standard InChI Key:  WFEFGXNOSOLREF-CFLFHXAXSA-N

Molfile:  

 
     RDKit          2D

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   19.8297   -4.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5445   -4.9889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2609   -4.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2580   -3.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5427   -3.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5403   -2.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9710   -3.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9760   -4.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6898   -4.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4049   -4.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1187   -4.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8338   -4.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5476   -4.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2626   -4.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2640   -5.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9765   -4.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6916   -4.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4054   -4.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1205   -4.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8342   -4.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4040   -3.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6928   -5.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4062   -5.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1149   -4.9879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1143   -5.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1163   -3.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1161   -2.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5494   -4.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  5  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 19 22  1  1
 18 23  1  6
 11 24  1  0
  2 25  1  0
 25 26  1  0
  1 27  1  0
 27 28  1  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4517191

   ---

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: 401.55

Molecular Weight (Monoisotopic): 401.2566

AlogP: 5.07

#Rotatable Bonds: 10

Polar Surface Area: 71.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.91

CX Basic pKa: 1.94

CX LogP: 5.14

CX LogD: 5.14

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: 1.71

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]

Source

Source(1):

• Scientific Literature