Aflaquinolone I; (3R,4R)-13-hydroxyaflaquinolone F

ID: ALA4474624

PubChem CID: 145721181

Max Phase: Preclinical

Molecular Formula: C15H13NO4

Molecular Weight: 271.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1Nc2ccccc2[C@](O)(c2cccc(O)c2)[C@H]1O

Standard InChI:  InChI=1S/C15H13NO4/c17-10-5-3-4-9(8-10)15(20)11-6-1-2-7-12(11)16-14(19)13(15)18/h1-8,13,17-18,20H,(H,16,19)/t13-,15+/m0/s1

Standard InChI Key:  JRZQVKOEUXXAPL-DZGCQCFKSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   29.5288   -2.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5277   -3.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2430   -3.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9602   -3.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9573   -2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2412   -2.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2395   -4.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2335   -6.1605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9505   -5.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9544   -4.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5203   -5.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5255   -4.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8177   -4.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1081   -4.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1068   -5.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8111   -6.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6642   -6.1645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6709   -2.0296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6700   -4.5099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8238   -3.9183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7 12  1  0
  7 10  1  0
 11  8  1  0
  8  9  1  0
  9 10  1  0
  3  7  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 17  2  0
  5 18  1  0
 10 19  1  1
  7 20  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4474624

   ---

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: 271.27

Molecular Weight (Monoisotopic): 271.0845

AlogP: 0.94

#Rotatable Bonds: 1

Polar Surface Area: 89.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.31

CX Basic pKa: ┄

CX LogP: 0.93

CX LogD: 0.93

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.62

Np Likeness Score: 1.33

References

1. El-Kashef DH, Daletos G, Plenker M, Hartmann R, Mándi A, Kurtán T, Weber H, Lin W, Ancheeva E, Proksch P..  (2019)  Polyketides and a Dihydroquinolone Alkaloid from a Marine-Derived Strain of the Fungus Metarhizium marquandii.,  82  (9): [PMID:31432669] [10.1021/acs.jnatprod.9b00125]

Source

Source(1):

• Scientific Literature