deconin A

ID: ALA3581619

PubChem CID: 122178986

Max Phase: Preclinical

Molecular Formula: C21H30O5

Molecular Weight: 362.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCC[C@]1(C)c1ccc(C(=O)OCC[C@@](C)(O)CC(=O)O)cc1

Standard InChI:  InChI=1S/C21H30O5/c1-19(2)10-5-11-21(19,4)16-8-6-15(7-9-16)18(24)26-13-12-20(3,25)14-17(22)23/h6-9,25H,5,10-14H2,1-4H3,(H,22,23)/t20-,21-/m1/s1

Standard InChI Key:  PMMJBYVOCQEGKR-NHCUHLMSSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -6.2296   -5.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1491   -6.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490    2.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9134    2.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0527    2.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    1.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9183    1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1697   -0.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022    0.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5966    2.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1872   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4854   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5257   -7.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4837   -9.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
  5  4  1  0
  6  5  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 13  5  1  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 16 13  1  0
  8 13  1  0
 13 17  1  1
 18 19  1  0
 18 20  2  0
 11 18  1  0
 19 21  1  0
 21 22  1  0
 22  2  1  0
  2 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3581619

   ---

Molecule Features

Natural Product: Yes

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: 362.47

Molecular Weight (Monoisotopic): 362.2093

AlogP: 3.93

#Rotatable Bonds: 7

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.85

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 0.72

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: 1.22

References

1. Surup F, Thongbai B, Kuhnert E, Sudarman E, Hyde KD, Stadler M..  (2015)  Deconins A-E: Cuparenic and Mevalonic or Propionic Acid Conjugates from the Basidiomycete Deconica sp. 471.,  78  (4): [PMID:25871540] [10.1021/np5010104]

Source

Source(1):

• Scientific Literature