Disparamide A

ID: ALA5191659

PubChem CID: 168286076

Max Phase: Preclinical

Molecular Formula: C24H27BrN10O2

Molecular Weight: 567.45

Names and Identifiers

Canonical SMILES:  CC(c1[nH]c(=N)[nH]c1/C=C/CNC(=O)c1ccc[nH]1)c1[nH]c(=N)[nH]c1/C=C/CNC(=O)c1cc(Br)c[nH]1

Standard InChI:  InChI=1S/C24H27BrN10O2/c1-13(19-15(32-23(26)34-19)5-2-9-29-21(36)17-7-4-8-28-17)20-16(33-24(27)35-20)6-3-10-30-22(37)18-11-14(25)12-31-18/h2-8,11-13,28,31H,9-10H2,1H3,(H,29,36)(H,30,37)(H3,26,32,34)(H3,27,33,35)/b5-2+,6-3+

Standard InChI Key:  SEXHFOBSTLFKPA-BUSIMMOISA-N

Molfile:  

 
     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -3.8758    4.0184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371    4.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0413    5.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883    4.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041    3.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450    2.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369    2.7762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938    2.3273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7777    1.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697    1.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    1.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0973    0.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7073    1.4300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238    1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566    0.2138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368    0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1383    1.4340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0242   -0.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368   -1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8009   -0.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2856   -1.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -1.0036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -0.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2856    0.0759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846    0.2336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0720   -2.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2750   -2.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0614   -3.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -3.2797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491   -4.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7461   -4.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3656   -4.6602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870   -3.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -4.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -5.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0416   -5.0603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8758   -4.0069    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 13 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 14 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 21 20  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 23 25  2  0
 21 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 33 31  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 31  1  0
 34 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5191659

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 567.45

Molecular Weight (Monoisotopic): 566.1502

AlogP: 2.41

#Rotatable Bonds: 10

Polar Surface Area: 200.64

Molecular Species: BASE

HBA: 4

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.27

CX Basic pKa: 23.45

CX LogP: 0.33

CX LogD: -4.36

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.14

Np Likeness Score: -0.05

References

1. Freire VF, Gubiani JR, Spencer TM, Hajdu E, Ferreira AG, Ferreira DAS, de Castro Levatti EV, Burdette JE, Camargo CH, Tempone AG, Berlinck RGS..  (2022)  Feature-Based Molecular Networking Discovery of Bromopyrrole Alkaloids from the Marine Sponge Agelas dispar.,  85  (5.0): [PMID:35427139] [10.1021/acs.jnatprod.2c00094]

Source

Source(1):

• Scientific Literature