(-)-Evodialone B

ID: ALA4527326

PubChem CID: 155544263

Max Phase: Preclinical

Molecular Formula: C19H26O7

Molecular Weight: 366.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]1(O)C(=O)[C@]2(CC=C(C)C)C[C@H](O)C(C)(C)OC2=C1C(C)=O

Standard InChI:  InChI=1S/C19H26O7/c1-10(2)7-8-18-9-12(21)17(4,5)26-14(18)13(11(3)20)19(24,15(18)22)16(23)25-6/h7,12,21,24H,8-9H2,1-6H3/t12-,18+,19+/m0/s1

Standard InChI Key:  ZQRQLDLOXZSDNY-GESALYCCSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   31.4000   -3.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6942   -3.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4045   -4.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2149   -3.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0321   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6271   -2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0321   -4.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7374   -4.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7374   -3.1037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3250   -4.7432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4427   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4472   -4.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2224   -4.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2152   -3.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4395   -5.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7296   -5.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7250   -6.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0149   -6.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4303   -6.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4634   -2.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2618   -2.3079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9133   -1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4791   -5.3531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4091   -5.1346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1099   -3.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8199   -4.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  5  7  1  0
  5  9  1  0
  7  8  1  0
  8 12  1  0
 11  9  1  0
  7 10  1  6
 11 12  1  0
 12 13  1  0
 13  2  1  0
  2 14  1  0
 14 11  2  0
 12 15  1  1
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 14 20  1  0
 20 21  2  0
 20 22  1  0
 13 23  2  0
  2  1  1  1
  3 24  2  0
  3 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527326

   ---

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: 366.41

Molecular Weight (Monoisotopic): 366.1679

AlogP: 1.22

#Rotatable Bonds: 4

Polar Surface Area: 110.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.86

CX Basic pKa: ┄

CX LogP: 1.08

CX LogD: 1.08

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: 2.36

References

1. Xu JF, Han C, Xu QQ, Wang XB, Zhao HJ, Xue GM, Luo JG, Kong LY..  (2019)  Isolation, Chiral-Phase Resolution, and Determination of the Absolute Configurations of a Complete Series of Stereoisomers of a Rearranged Acetophenone with Three Stereocenters.,  82  (6): [PMID:30998015] [10.1021/acs.jnatprod.8b00003]

Source

Source(1):

• Scientific Literature