Strepantibin B

ID: ALA4557294

PubChem CID: 145720921

Max Phase: Preclinical

Molecular Formula: C21H17NO2

Molecular Weight: 315.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)N=C2C(c3ccccc3)=CC(=O)C(c3ccccc3)=C2O1

Standard InChI:  InChI=1S/C21H17NO2/c1-21(2)22-19-16(14-9-5-3-6-10-14)13-17(23)18(20(19)24-21)15-11-7-4-8-12-15/h3-13H,1-2H3

Standard InChI Key:  QUVACELBKBUEBZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   12.3610   -7.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3652   -6.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6513   -6.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5065   -2.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5054   -3.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2134   -4.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9272   -3.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9244   -2.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2116   -2.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6374   -4.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0587   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0594   -4.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3465   -3.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7658   -5.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7627   -6.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4728   -6.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1824   -6.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1815   -5.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4750   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3451   -5.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6393   -5.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0334   -5.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1769   -6.2194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3460   -2.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 21  2  0
 10 13  1  0
 20 11  1  0
 11 12  2  0
 12 13  1  0
  7 10  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 11 14  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
  2 23  1  0
 23 20  2  0
 13 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557294

   ---

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: 315.37

Molecular Weight (Monoisotopic): 315.1259

AlogP: 4.27

#Rotatable Bonds: 2

Polar Surface Area: 38.66

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.61

CX LogD: 4.61

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 0.91

References

1. Song YJ, Zheng HB, Peng AH, Ma JH, Lu DD, Li X, Zhang HY, Xie WD..  (2019)  Strepantibins A-C: Hexokinase II Inhibitors from a Mud Dauber Wasp Associated Streptomyces sp.,  82  (5): [PMID:31013087] [10.1021/acs.jnatprod.8b00821]

Source

Source(1):

• Scientific Literature