Herboxidiene methyl ester

ID: ALA2288585

PubChem CID: 10950472

Max Phase: Preclinical

Molecular Formula: C26H44O6

Molecular Weight: 452.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C[C@H]1CC[C@H](C)[C@@H](/C(C)=C/C=C/[C@@H](C)C[C@@]2(C)O[C@@H]2[C@H](C)[C@@H](OC)[C@@H](C)O)O1

Standard InChI:  InChI=1S/C26H44O6/c1-16(15-26(6)25(32-26)19(4)24(30-8)20(5)27)10-9-11-17(2)23-18(3)12-13-21(31-23)14-22(28)29-7/h9-11,16,18-21,23-25,27H,12-15H2,1-8H3/b10-9+,17-11+/t16-,18+,19-,20-,21-,23-,24-,25-,26-/m1/s1

Standard InChI Key:  HMHMUCAMCRPACN-DGJNZOEVSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   10.9793   -4.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9793   -4.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6913   -5.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4034   -4.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4034   -4.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6913   -3.6959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1191   -3.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2636   -3.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1215   -2.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8372   -2.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4082   -2.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8410   -3.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5564   -4.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -4.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5504   -2.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4121   -3.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7002   -4.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2654   -5.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2591   -2.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4067   -2.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4913   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -4.4459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769   -3.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1562   -3.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4348   -3.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4208   -2.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7274   -3.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061   -3.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415   -4.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0342   -5.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2987   -3.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9921   -2.5413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  1
  1  8  1  1
  7  9  1  0
  9 10  1  0
  9 11  2  0
 12 13  1  0
 13  8  2  0
 12 14  2  0
 10 15  1  0
 14 16  1  0
 16 17  1  0
 23 17  1  0
  2 18  1  6
  8 19  1  0
 16 20  1  6
 23 21  1  6
 23 22  1  0
 24 23  1  0
 24 22  1  6
 24 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 27 29  1  1
 29 30  1  0
 28 31  1  0
 28 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2288585

   HERBOXIDIENE METHYL ESTER

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: 452.63

Molecular Weight (Monoisotopic): 452.3138

AlogP: 4.45

#Rotatable Bonds: 11

Polar Surface Area: 77.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: 1.86

References

1. Edmunds AJ, Arnold G, Hagmann L, Schaffner R, Furlenmeier H..  (2000)  Synthesis of simplified herboxidiene aromatic hybrids.,  10  (12): [PMID:10890165] [10.1016/s0960-894x(00)00230-4]

2. Granatosky EA, DiPrimio N, Pickering JRE, Stevens DC, Perlstein EO, Taylor RE..  (2018)  GEX1A, a Polyketide from Streptomyces chromofuscus, Corrects the Cellular Defects Associated with Niemann-Pick Type C1 in Human Fibroblasts.,  81  (9): [PMID:30188717] [10.1021/acs.jnatprod.8b00314]

Source

Source(1):

• Scientific Literature