(+)-Aplysamine 7

ID: ALA2332123

PubChem CID: 71665144

Max Phase: Preclinical

Molecular Formula: C23H28Br3N3O5

Molecular Weight: 666.21

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-Aplysamine 7 | (+)-Aplysamine 7|CHEMBL2332123

Canonical SMILES:  COc1ccc(C/C(=N\O)C(=O)NC[C@@H](O)c2cc(Br)c(OCCCN(C)C)c(Br)c2)cc1Br

Standard InChI:  InChI=1S/C23H28Br3N3O5/c1-29(2)7-4-8-34-22-17(25)11-15(12-18(22)26)20(30)13-27-23(31)19(28-32)10-14-5-6-21(33-3)16(24)9-14/h5-6,9,11-12,20,30,32H,4,7-8,10,13H2,1-3H3,(H,27,31)/b28-19+/t20-/m1/s1

Standard InChI Key:  FZBQAWDXVQGOIC-WDMWBOBFSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   15.2718   -2.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2706   -3.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9860   -3.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7030   -3.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7002   -2.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9842   -2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9818   -1.4797    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.5594   -3.9568    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.5608   -2.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8458   -2.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1307   -2.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4158   -2.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7006   -2.3058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9857   -2.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7004   -1.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4147   -3.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4156   -4.7789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1292   -3.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8447   -3.9522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5593   -3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2707   -3.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5584   -2.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2716   -4.7756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9872   -5.1894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9852   -3.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7008   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6974   -4.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4121   -5.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1276   -4.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1240   -3.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4088   -3.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8372   -3.5281    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   23.8437   -5.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8457   -6.0089    0.0000 C   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
  6  7  1  0
  2  8  1  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  4 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 30 32  1  0
 29 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332123

   (+)-Aplysamine 7

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: 666.21

Molecular Weight (Monoisotopic): 662.9579

AlogP: 4.54

#Rotatable Bonds: 12

Polar Surface Area: 103.62

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.09

CX Basic pKa: 9.29

CX LogP: 3.28

CX LogD: 2.72

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.13

Np Likeness Score: 0.06

References

1. Tran TD, Pham NB, Fechner G, Hooper JN, Quinn RJ..  (2013)  Bromotyrosine alkaloids from the Australian marine sponge Pseudoceratina verrucosa.,  76  (4): [PMID:23489291] [10.1021/np300648d]

Source

Source(1):

• Scientific Literature