Aplysinellamide C

ID: ALA3286790

PubChem CID: 90680650

Max Phase: Preclinical

Molecular Formula: C15H18BrNO4

Molecular Weight: 356.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)NCCCCC(=O)O)cc1Br

Standard InChI:  InChI=1S/C15H18BrNO4/c1-21-13-7-5-11(10-12(13)16)6-8-14(18)17-9-3-2-4-15(19)20/h5-8,10H,2-4,9H2,1H3,(H,17,18)(H,19,20)/b8-6+

Standard InChI Key:  MYLDQRMKMYARSW-SOFGYWHQSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   34.2835   -3.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2823   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9904   -4.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7000   -4.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6972   -3.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9886   -2.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4034   -2.9323    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   36.4084   -4.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4097   -5.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5757   -2.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8681   -3.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1602   -2.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4526   -3.3478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1601   -2.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7448   -2.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0372   -3.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3294   -2.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6218   -3.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9140   -2.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9128   -2.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2054   -3.3481    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
  5  7  1  0
  4  8  1  0
  8  9  1  0
  1 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3286790

   5-[[(E)-3-(3-bromo-4-methoxyphenyl)prop-2-enoyl]amino]pentanoic acid

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: 356.22

Molecular Weight (Monoisotopic): 355.0419

AlogP: 2.84

#Rotatable Bonds: 8

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.44

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: -0.24

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: 0.01

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