Securamine I

ID: ALA4161989

PubChem CID: 145960199

Max Phase: Preclinical

Molecular Formula: C20H17Br2ClN4O2

Molecular Weight: 540.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)[C@@H](Cl)C[C@]23[C@@H]4CC(=O)N2C=CC2=NC(=O)N[C@@]21N3c1cc(Br)c(Br)cc14

Standard InChI:  InChI=1S/C20H17Br2ClN4O2/c1-18(2)14(23)8-19-10-6-16(28)26(19)4-3-15-20(18,25-17(29)24-15)27(19)13-7-12(22)11(21)5-9(10)13/h3-5,7,10,14H,6,8H2,1-2H3,(H,25,29)/t10-,14+,19+,20-/m1/s1

Standard InChI Key:  QPSBWLFZQVNMFU-QXQMREQMSA-N

Molfile:  

     RDKit          2D

 30 35  0  0  0  0  0  0  0  0999 V2000
   16.9547   -6.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2365   -6.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4277   -6.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6121   -5.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3550   -5.3756    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2365   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9634   -4.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9623   -5.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6084   -5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6066   -3.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2492   -4.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2540   -5.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9561   -4.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1078   -4.4666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1007   -3.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3902   -3.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9611   -5.3118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3976   -4.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5902   -5.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5609   -5.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0394   -6.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3279   -6.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8357   -6.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2412   -7.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9822   -7.1342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5786   -3.4545    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6962   -3.2801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3175   -3.9670    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.3162   -5.4615    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   13.9516   -8.0291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  6
  4  6  1  0
  4  2  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 12 17  1  0
 13 11  1  0
 13 18  1  0
 18 14  1  1
 14 15  1  0
 15 16  1  0
 16 13  1  0
 17 18  1  0
 17 22  1  0
 19 20  2  0
 21 20  1  0
 19 14  1  0
 18  6  1  0
 22  2  1  0
 22 21  1  1
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  2  0
 13 26  1  6
 15 27  2  0
  7 28  1  0
  8 29  1  0
 24 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4161989

   ---

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: 540.64

Molecular Weight (Monoisotopic): 537.9407

AlogP: 4.47

#Rotatable Bonds: ┄

Polar Surface Area: 65.01

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.42

CX Basic pKa: 0.13

CX LogP: 5.01

CX LogD: 5.01

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: 0.65

References

1. Hansen KØ, Isaksson J, Bayer A, Johansen JA, Andersen JH, Hansen E..  (2017)  Securamine Derivatives from the Arctic Bryozoan Securiflustra securifrons.,  80  (12): [PMID:29220180] [10.1021/acs.jnatprod.7b00703]

Source

Source(1):

• Scientific Literature