aphrocallistin

ID: ALA1086155

PubChem CID: 135914520

Max Phase: Preclinical

Molecular Formula: C20H24Br2N6O2

Molecular Weight: 540.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Aphrocallistin

Canonical SMILES:  CC(=O)N(C)CCc1cc(Br)c(OCCCNc2ncn(C)c3ncnc2-3)c(Br)c1

Standard InChI:  InChI=1S/C20H24Br2N6O2/c1-13(29)27(2)7-5-14-9-15(21)18(16(22)10-14)30-8-4-6-23-19-17-20(25-11-24-17)28(3)12-26-19/h9-12,23H,4-8H2,1-3H3

Standard InChI Key:  ONIZXWNHLRRDOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.0639    0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651    0.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6497   -0.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662    0.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3633    0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6479    1.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785    1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    1.3787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218    0.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2076    2.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6364    1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6495   -1.0985    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0762    1.3855    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0813   -0.2716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7951    0.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5102   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2240    0.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9392   -0.2671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6530    0.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0816    0.9652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667    1.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6488    0.9670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0787    0.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3670   -0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5363   -1.0729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3528   -1.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6878   -0.4106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970    1.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5 15  1  0
  3  4  2  0
  4 16  1  0
  7  8  1  0
 16 17  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
 21 26  2  0
  2  3  1  0
  9 11  1  0
  5  6  2  0
 21 24  1  0
 25 22  1  0
 22 23  1  0
 23 24  2  0
 25 26  1  0
 10 12  1  0
  6  1  1  0
 10 13  2  0
  1  2  2  0
  3 14  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 25  2  0
  1  7  1  0
 22 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086155

   APHROCALLISTIN

Molecule Features

Natural Product: Yes

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: 540.26

Molecular Weight (Monoisotopic): 538.0327

AlogP: 3.74

#Rotatable Bonds: 9

Polar Surface Area: 85.17

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.08

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -0.63

References

1. Wright AE, Roth GP, Hoffman JK, Divlianska DB, Pechter D, Sennett SH, Guzmán EA, Linley P, McCarthy PJ, Pitts TP, Pomponi SA, Reed JK..  (2009)  Isolation, synthesis, and biological activity of aphrocallistin, an adenine-substituted bromotyramine metabolite from the Hexactinellida sponge Aphrocallistes beatrix.,  72  (6): [PMID:19459694] [10.1021/np900183v]

Source

Source(1):

• Scientific Literature