Aplysinellamide A

ID: ALA3286788

PubChem CID: 118705727

Max Phase: Preclinical

Molecular Formula: C18H22BrF3N2O6

Molecular Weight: 385.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)NCCCC[C@@H](N)C(=O)O)cc1Br.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C16H21BrN2O4.C2HF3O2/c1-23-14-7-5-11(10-12(14)17)6-8-15(20)19-9-3-2-4-13(18)16(21)22;3-2(4,5)1(6)7/h5-8,10,13H,2-4,9,18H2,1H3,(H,19,20)(H,21,22);(H,6,7)/b8-6+;/t13-;/m1./s1

Standard InChI Key:  PBPMQMRDASNOSM-LOSTWAFRSA-N

Molfile:  

     RDKit          2D

 30 29  0  0  0  0  0  0  0  0999 V2000
    4.2468   -4.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606   -3.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -4.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6576   -5.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2435   -5.9372    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4826   -5.2255    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -5.9333    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0318   -2.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0307   -3.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7454   -3.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4619   -3.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4590   -2.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7436   -2.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1719   -2.3353    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.1770   -3.9923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1783   -4.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3172   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029   -2.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8883   -2.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1740   -2.7547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8881   -1.5171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4594   -2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7451   -2.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305   -2.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161   -2.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015   -2.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871   -2.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013   -1.5182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713   -2.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8860   -3.5831    0.0000 O   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
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: 385.26

Molecular Weight (Monoisotopic): 384.0685

AlogP: 2.17

#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: -0.18

CX LogD: -0.19

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.45

Np Likeness Score: 0.30

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