Fusariumin

ID: ALA1684400

PubChem CID: 53322161

Max Phase: Preclinical

Molecular Formula: C18H22O5

Molecular Weight: 318.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fusariumin | Fusariumin|CHEMBL1684400|CHEBI:210089|6,8-dihydroxy-3-[(E,8S)-8-hydroxynon-5-enyl]isochromen-1-one

Canonical SMILES:  C[C@H](O)C/C=C/CCCCc1cc2cc(O)cc(O)c2c(=O)o1

Standard InChI:  InChI=1S/C18H22O5/c1-12(19)7-5-3-2-4-6-8-15-10-13-9-14(20)11-16(21)17(13)18(22)23-15/h3,5,9-12,19-21H,2,4,6-8H2,1H3/b5-3+/t12-/m0/s1

Standard InChI Key:  MIICTKRWRNNLEI-PYEVWLCESA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -1.0681    1.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693    1.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3544    0.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3562    2.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591    1.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579    1.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748    0.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975    1.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987    1.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0772    2.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773    3.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    3.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841    0.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    0.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264    1.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6554    1.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3687    0.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0843    1.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7976    0.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5132    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2266    0.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5156    1.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
  4 12  1  0
  2  3  1  0
  2 13  1  0
  3  6  2  0
  8 14  1  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
  7  8  2  0
 19 20  1  0
  8  9  1  0
 20 21  1  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 21 23  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1684400

   FUSARIUMIN

Molecule Features

Natural Product: No

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: 318.37

Molecular Weight (Monoisotopic): 318.1467

AlogP: 3.24

#Rotatable Bonds: 7

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.43

CX Basic pKa: ┄

CX LogP: 4.11

CX LogD: 4.07

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: 2.12

References

1. Yang SX, Gao JM, Zhang Q, Laatsch H..  (2011)  Toxic polyketides produced by Fusarium sp., an endophytic fungus isolated from Melia azedarach.,  21  (6): [PMID:21353539] [10.1016/j.bmcl.2010.12.043]

Source

Source(1):

• Scientific Literature