Rhizoxin T3

ID: ALA4565874

PubChem CID: 155545142

Max Phase: Preclinical

Molecular Formula: C35H49NO10

Molecular Weight: 643.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@@H](/C(C)=C/C=C/C(C)=C/c1coc(C)n1)[C@@H](C)[C@@H]1C[C@H](O)[C@@](C)(O)/C=C/[C@H](O)[C@@H](C)[C@H]2C[C@H](CC(=O)O2)C[C@@H]2O[C@H]2C(=O)O1

Standard InChI:  InChI=1S/C35H49NO10/c1-19(13-25-18-43-23(5)36-25)9-8-10-20(2)32(42-7)22(4)28-17-30(38)35(6,41)12-11-26(37)21(3)27-14-24(16-31(39)44-27)15-29-33(45-29)34(40)46-28/h8-13,18,21-22,24,26-30,32-33,37-38,41H,14-17H2,1-7H3/b9-8+,12-11+,19-13+,20-10+/t21-,22+,24+,26+,27-,28+,29+,30+,32+,33-,35+/m1/s1

Standard InChI Key:  MGMHBFBKYBCOPO-RKNMXKMUSA-N

Molfile:  

 
     RDKit          2D

 51 54  0  0  0  0  0  0  0  0999 V2000
   40.7688  -14.6599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0630  -15.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7733  -15.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3614  -15.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3614  -16.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0667  -16.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7726  -16.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.4788  -16.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9047  -15.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0710  -14.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7891  -13.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5136  -12.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7952  -13.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2196  -13.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2048  -13.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9033  -14.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6210  -13.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6358  -13.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9329  -12.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.2133  -12.2290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.5244  -11.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1926  -15.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1950  -16.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9032  -15.9031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6483  -15.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0675  -17.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3603  -17.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7798  -17.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6480  -17.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3611  -18.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0693  -19.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4738  -17.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.9025  -16.7235    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   42.8984  -13.4671    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   44.3553  -12.6790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.6471  -16.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9366  -17.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2243  -17.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5129  -17.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8007  -17.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0893  -17.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7998  -16.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3811  -17.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2882  -16.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4846  -16.5541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0767  -17.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6284  -17.8771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.2543  -17.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0589  -15.8940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.4786  -15.0891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   40.0916  -12.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  5  1  0
  4  2  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 23  1  0
 22  9  1  0
  9 16  1  0
  2 10  1  0
 11 10  2  0
 11 13  1  0
 14 12  1  0
 12 13  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 20  1  1
 12 21  1  1
 23 22  1  0
 24 23  1  0
 22 24  1  0
  4 25  1  6
  6 26  1  0
 26 27  1  0
 26 28  1  6
 27 29  1  0
 27 30  1  1
 30 31  1  0
  8 32  2  0
 23 33  1  6
 16 34  1  1
 18 35  2  0
 29 36  1  0
 29 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 40 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  1  0
 46 47  2  0
 47 43  1  0
 46 48  1  0
  6 49  1  1
 22 50  1  1
 13 51  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4565874

   ---

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: 643.77

Molecular Weight (Monoisotopic): 643.3356

AlogP: 4.00

#Rotatable Bonds: 7

Polar Surface Area: 161.08

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.42

CX Basic pKa: 0.58

CX LogP: 2.45

CX LogD: 2.45

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.17

Np Likeness Score: 2.36

References

1. Carter AC, Petersen CL, Wendt KL, Helff SK, Risinger AL, Mooberry SL, Cichewicz RH..  (2019)  In Situ Ring Contraction and Transformation of the Rhizoxin Macrocycle through an Abiotic Pathway.,  82  (4): [PMID:30865445] [10.1021/acs.jnatprod.8b00974]

Source

Source(1):

• Scientific Literature