2,3-Dihydrophysachenolide C

ID: ALA4878643

PubChem CID: 164626902

Max Phase: Preclinical

Molecular Formula: C30H42O9

Molecular Weight: 546.66

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@]12CC[C@H]3[C@@H](C[C@H]4O[C@]45CCCC(=O)[C@]35C)[C@]1(O)CC[C@@]2(O)[C@@](C)(O)C1CC(C)=C(C)C(=O)O1

Standard InChI:  InChI=1S/C30H42O9/c1-16-13-22(38-24(33)17(16)2)26(5,34)30(36)12-11-28(35)20-14-23-29(39-23)9-6-7-21(32)25(29,4)19(20)8-10-27(28,30)15-37-18(3)31/h19-20,22-23,34-36H,6-15H2,1-5H3/t19-,20+,22?,23+,25-,26-,27+,28+,29+,30+/m0/s1

Standard InChI Key:  PLMVDZBEQUQDAZ-KDMRXNLTSA-N

Molfile:  

 
     RDKit          2D

 42 47  0  0  0  0  0  0  0  0999 V2000
    6.7468  -12.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5469  -13.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3345  -12.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9296  -15.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9296  -16.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416  -16.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416  -14.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3538  -15.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7760  -16.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0662  -14.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756  -15.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7926  -13.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715  -14.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5021  -14.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4931  -14.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2718  -15.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7621  -14.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2864  -13.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3587  -12.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9026  -13.5039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7084  -13.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9761  -12.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4315  -11.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6193  -12.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416  -14.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464  -14.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967  -13.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7795  -12.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7741  -12.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0570  -11.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4861  -11.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4884  -15.7146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1094  -13.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6976  -11.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7856  -12.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2515  -13.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0591  -15.6980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7674  -14.4686    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0592  -16.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3517  -16.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527  -16.9329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425  -17.1066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  1  0
  4  7  1  0
  5  6  1  0
  6 40  1  0
  8  7  1  0
  8 40  1  0
  8 10  1  0
 39  9  1  0
  9 11  1  0
 10 11  1  0
 10 13  1  0
 11 15  1  0
 14 12  1  0
 12 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 18  2  1  0
  2 19  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
  7 25  2  0
  8 26  1  1
 14 27  1  1
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 15 32  1  6
 18 33  1  1
 23 34  1  0
 22 35  1  0
 21 36  2  0
 10 37  1  6
 11 38  1  1
 40 39  1  0
 40 41  1  1
 39 41  1  0
 39 42  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4878643

   ---

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: 546.66

Molecular Weight (Monoisotopic): 546.2829

AlogP: 2.52

#Rotatable Bonds: 4

Polar Surface Area: 142.89

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.36

Np Likeness Score: 3.18

References

1. Kithsiri Wijeratne EM, Xu YM, Liu MX, Inacio MC, Brooks AD, Tewary P, Sayers TJ, Gunatilaka AAL..  (2021)  Ring A/B-Modified 17β-Hydroxywithanolide Analogues as Antiproliferative Agents for Prostate Cancer and Potentiators of Immunotherapy for Renal Carcinoma and Melanoma.,  84  (12.0): [PMID:34851111] [10.1021/acs.jnatprod.1c00724]

Source

Source(1):

• Scientific Literature