(2R,3S,6R,7R)-15-(4-hydroxy-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,9,11,13-hexamethyl-pentadeca-4,8,10,13-tetraene-2,3,6-triol

ID: ALA4472557

PubChem CID: 155535981

Max Phase: Preclinical

Molecular Formula: C29H45NO6

Molecular Weight: 503.68

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H45NO6/c1-17(11-12-24-22(6)26(33)27(35-9)28(30-24)36-10)13-18(2)14-19(3)15-20(4)25(32)21(5)16-29(8,34)23(7)31/h11,14-16,20,23,25,31-32,34H,12-13H2,1-10H3,(H,30,33)/b17-11+,18-14+,19-15+,21-16+/t20-,23-,25-,29+/m1/s1

Standard InChI Key:  WLTRGKYFEWQYDP-ZNBNPLEZSA-N

Molfile:  

 
     RDKit          2D

 36 36  0  0  0  0  0  0  0  0999 V2000
    4.2946  -11.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2935  -11.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0015  -12.2924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7112  -11.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084  -11.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997  -10.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9973   -9.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145  -10.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4195  -12.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1266  -11.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8349  -12.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5420  -11.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2504  -12.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9574  -11.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658  -12.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6671  -13.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3728  -11.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0812  -12.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7883  -11.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4966  -12.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2037  -11.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9120  -12.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4979  -13.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7870  -11.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0825  -13.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8362  -13.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5854  -12.2914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848  -13.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868  -10.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866   -9.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2516  -13.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9133  -13.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6191  -11.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3274  -12.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6178  -11.0502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9075  -11.4572    0.0000 O   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
 21 22  1  0
 20 23  1  0
 19 24  1  1
 18 25  1  6
 11 26  1  0
  2 27  1  0
 27 28  1  0
  1 29  1  0
 29 30  1  0
 13 31  1  0
 22 32  1  0
 22 33  1  0
 33 34  1  0
 33 35  1  6
 22 36  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4472557

   ---

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: 503.68

Molecular Weight (Monoisotopic): 503.3247

AlogP: 4.96

#Rotatable Bonds: 12

Polar Surface Area: 112.27

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.90

CX Basic pKa: 1.94

CX LogP: 4.41

CX LogD: 4.41

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.24

Np Likeness Score: 1.47

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