(-)-17-Hydroxybrevianamide N

ID: ALA4875921

PubChem CID: 164628859

Max Phase: Preclinical

Molecular Formula: C18H13N3O4

Molecular Weight: 335.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)[C@@H](Cc2ccccc2O)n2c1nc1ccccc1c2=O

Standard InChI:  InChI=1S/C18H13N3O4/c22-14-8-4-1-5-10(14)9-13-16(23)20-17(24)15-19-12-7-3-2-6-11(12)18(25)21(13)15/h1-8,13,22H,9H2,(H,20,23,24)/t13-/m1/s1

Standard InChI Key:  FWYQOSQGSCRKJR-CYBMUJFWSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   12.9911   -1.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9900   -2.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6980   -2.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4077   -2.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4048   -1.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6962   -1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2833   -1.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2819   -2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2813   -3.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2729   -5.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9827   -4.7515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9870   -3.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6962   -3.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5673   -4.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5668   -3.9299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8644   -3.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8654   -5.1556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1584   -4.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1612   -3.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4607   -3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7568   -3.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7579   -4.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4590   -5.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8627   -2.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2692   -5.9754    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
  1  7  1  0
  2  8  1  0
  9  8  1  6
  9 15  1  0
  9 12  1  0
 14 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 14 15  1  0
 14 17  2  0
 15 16  1  0
 16 19  1  0
 18 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 16 24  2  0
 10 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875921

   ---

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: 335.32

Molecular Weight (Monoisotopic): 335.0906

AlogP: 1.16

#Rotatable Bonds: 2

Polar Surface Area: 101.29

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.58

CX Basic pKa: 1.18

CX LogP: 1.76

CX LogD: 1.73

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: 0.42

References

1. Xu WF, Chao R, Hai Y, Guo YY, Wei MY, Wang CY, Shao CL..  (2021)  17-Hydroxybrevianamide N and Its N1-Methyl Derivative, Quinazolinones from a Soft-Coral-Derived Aspergillus sp. Fungus: 13S Enantiomers as the True Natural Products.,  84  (4.0): [PMID:33765387] [10.1021/acs.jnatprod.1c00098]

Source

Source(1):

• Scientific Literature