Versicolorin B

ID: ALA4744009

Cas Number: 4331-22-0

PubChem CID: 107849

Max Phase: Preclinical

Molecular Formula: C18H12O7

Molecular Weight: 340.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1c2cc(O)cc(O)c2C(=O)c2c1cc1c(c2O)[C@@H]2CCO[C@@H]2O1

Standard InChI:  InChI=1S/C18H12O7/c19-6-3-8-12(10(20)4-6)16(22)14-9(15(8)21)5-11-13(17(14)23)7-1-2-24-18(7)25-11/h3-5,7,18-20,23H,1-2H2/t7-,18+/m0/s1

Standard InChI Key:  BABJNKGTTYCTOO-ULCDLSAGSA-N

Molfile:  

 
     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   31.7214  -12.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7202  -13.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4361  -13.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4343  -11.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1509  -12.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1497  -13.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8596  -13.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8619  -11.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5805  -12.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5788  -13.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2923  -13.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2916  -11.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4319  -11.0193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0043  -13.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8590  -14.3224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8619  -11.0129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2897  -11.0194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0056  -12.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0109  -13.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7971  -13.3291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7886  -11.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2818  -12.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0622  -12.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0528  -11.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2667  -11.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5687  -11.1897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.9877  -13.0650    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 19  2  0
 18 12  2  0
 12  9  1  0
  4 13  1  0
  2 14  1  0
  7 15  2  0
  8 16  2  0
 12 17  1  0
 18 19  1  0
 19 20  1  0
 20 22  1  0
 21 18  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 21 26  1  1
 22 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4744009

   Versicolorin B

Molecule Features

Natural Product: Yes

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: 340.29

Molecular Weight (Monoisotopic): 340.0583

AlogP: 1.80

#Rotatable Bonds: ┄

Polar Surface Area: 113.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.29

CX Basic pKa: ┄

CX LogP: 3.25

CX LogD: 2.87

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: 2.26

References

1. Ge H,Shi M,Ma M,Lian XY,Zhang Z.  (2021)  Evaluation of the antiproliferative activity of 106 marine microbial metabolites against human lung cancer cells and potential antiproliferative mechanism of purpuride G.,  39  [PMID:33691166] [10.1016/j.bmcl.2021.127915]

Source

Source(1):

• Scientific Literature