Mandelalide A

ID: ALA5279714

Max Phase: Preclinical

Molecular Formula: C32H50O11

Molecular Weight: 610.74

Names and Identifiers

Canonical SMILES:  CO[C@H]1[C@H](O[C@@H]2C[C@@H]3C/C=C/C(=O)O[C@H](CO)C[C@H](O)[C@@H]4C[C@H](C)[C@H](/C=C\C=C\[C@H](C)C[C@H](C2)O3)O4)O[C@@H](C)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C32H50O11/c1-18-8-5-6-10-26-19(2)13-27(43-26)25(34)16-24(17-33)41-28(35)11-7-9-21-14-23(15-22(12-18)40-21)42-32-31(38-4)30(37)29(36)20(3)39-32/h5-8,10-11,18-27,29-34,36-37H,9,12-17H2,1-4H3/b8-5+,10-6-,11-7+/t18-,19-,20-,21-,22+,23+,24-,25-,26-,27-,29-,30+,31+,32-/m0/s1

Standard InChI Key:  CIXUVBCUYFVVDI-QQIONGNDSA-N

Molfile:  

 
     RDKit          2D

 48 51  0  0  0  0  0  0  0  0999 V2000
    0.2086    2.6639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0688    3.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5416    3.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    3.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5128    2.9414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175    2.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279    3.2188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840    1.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8458    1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400    0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4018   -0.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081    0.3885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7347    0.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562    0.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -0.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1776    0.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1222    1.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158    1.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158    2.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054    3.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1222    4.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175    4.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    3.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562    2.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    4.2188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    4.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9279    3.6360    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0688   -0.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4018   -0.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -2.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -3.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8201   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5427   -3.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5427   -2.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8201   -2.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2652   -2.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2652   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8201   -4.6135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474   -3.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.6934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    0.8343    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551   -0.4416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9568    4.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615    4.0513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 21 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
 24 25  1  0
 25 21  1  0
 24 26  1  6
 22 27  1  1
 21 28  1  6
 13 29  1  0
 29 30  1  0
 30 31  1  0
 31 11  1  0
 30 32  1  0
 33 32  1  1
 34 33  1  0
 35 34  1  0
 36 35  1  0
 37 36  1  0
 38 37  1  0
 33 38  1  0
 37 39  1  6
 36 40  1  1
 35 41  1  6
 34 42  1  6
 42 43  1  0
 30 44  1  6
 13 45  1  6
 11 46  1  6
  4 47  1  1
 47 48  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279714

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 610.74

Molecular Weight (Monoisotopic): 610.3353

AlogP: 1.95

#Rotatable Bonds: 4

Polar Surface Area: 153.37

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.73

CX Basic pKa: ┄

CX LogP: 1.85

CX LogD: 1.85

Aromatic Rings: ┄

Heavy Atoms: 43

QED Weighted: 0.35

Np Likeness Score: 2.68

References

1. Patel BA, D'Amico TL, Blagg BSJ..  (2020)  Natural products and other inhibitors of F₁F_O ATP synthase.,  207  [PMID:32942072] [10.1016/j.ejmech.2020.112779]

Source

Source(1):

• Scientific Literature