Fusarilactone B

ID: ALA5200933

PubChem CID: 87934518

Max Phase: Preclinical

Molecular Formula: C17H26O5

Molecular Weight: 310.39

Names and Identifiers

Canonical SMILES:  CC(=C\C(=O)O)/C=C(\C)CCCCCC[C@H]1OC(=O)[C@@H]1CO

Standard InChI:  InChI=1S/C17H26O5/c1-12(9-13(2)10-16(19)20)7-5-3-4-6-8-15-14(11-18)17(21)22-15/h9-10,14-15,18H,3-8,11H2,1-2H3,(H,19,20)/b12-9+,13-10+/t14-,15-/m1/s1

Standard InChI Key:  DJCXVFBEHFTGPG-KGQDJUJMSA-N

Molfile:  

 
     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    0.5301   -0.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -0.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161   -0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2793   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022   -1.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5653   -2.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -2.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8514   -2.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7480   -1.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1759   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928   -0.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7559    0.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788    0.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419    1.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8648    1.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887    1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0285    0.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8514    0.8641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    0.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5486    2.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2910    2.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
  3 11  1  0
  1 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 16 20  1  0
 17 21  1  6
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5200933

   (2E,4E)-11-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetan-2-yl]-3,5-dimethylundeca-2,4-dienoic acid

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: 310.39

Molecular Weight (Monoisotopic): 310.1780

AlogP: 2.84

#Rotatable Bonds: 10

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: 4.82

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 0.33

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.28

Np Likeness Score: 2.21

References

1. Li K, Chen S, Pang X, Cai J, Zhang X, Liu Y, Zhu Y, Zhou X..  (2022)  Natural products from mangrove sediments-derived microbes: Structural diversity, bioactivities, biosynthesis, and total synthesis.,  230  [PMID:35063731] [10.1016/j.ejmech.2022.114117]

Source

Source(1):

• Scientific Literature