Aplysinellamide B

ID: ALA3286789

PubChem CID: 118705728

Max Phase: Preclinical

Molecular Formula: C18H21Br2F3N2O6

Molecular Weight: 464.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(Br)cc(/C=C/C(=O)NCCCC[C@@H](N)C(=O)O)cc1Br.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C16H20Br2N2O4.C2HF3O2/c1-24-15-11(17)8-10(9-12(15)18)5-6-14(21)20-7-3-2-4-13(19)16(22)23;3-2(4,5)1(6)7/h5-6,8-9,13H,2-4,7,19H2,1H3,(H,20,21)(H,22,23);(H,6,7)/b6-5+;/t13-;/m1./s1

Standard InChI Key:  WULCNQXVXLPHMC-DHQBOWJTSA-N

Molfile:  

     RDKit          2D

 31 30  0  0  0  0  0  0  0  0999 V2000
   17.3966   -4.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8104   -3.7831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5716   -4.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8075   -5.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3935   -5.9247    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.6325   -5.2130    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.2123   -5.9208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.1526   -2.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1513   -3.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8662   -3.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5826   -3.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5797   -2.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8644   -2.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2927   -2.3020    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   24.2977   -3.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2989   -4.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4380   -2.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7235   -2.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0090   -2.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2946   -2.7214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0088   -1.4838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5801   -2.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8657   -2.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1512   -2.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4368   -2.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7223   -2.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0079   -2.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7221   -1.4848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2920   -2.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0068   -3.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8660   -4.7860    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  4  5  1  0
  4  6  1  0
  4  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
  8 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  6
 27 29  1  0
 27 30  2  0
 10 31  1  0
M  END

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: 464.15

Molecular Weight (Monoisotopic): 461.9790

AlogP: 2.93

#Rotatable Bonds: 9

Polar Surface Area: 101.65

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.27

CX Basic pKa: 9.53

CX LogP: 0.59

CX LogD: 0.58

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.39

Np Likeness Score: 0.45

References

1. Tian LW, Feng Y, Shimizu Y, Pfeifer T, Wellington C, Hooper JN, Quinn RJ..  (2014)  Aplysinellamides A-C, bromotyrosine-derived metabolites from an Australian Aplysinella sp. marine sponge.,  77  (5): [PMID:24758268] [10.1021/np500119e]

Source

Source(1):

• Scientific Literature