Securamine H

ID: ALA4169917

PubChem CID: 145953284

Max Phase: Preclinical

Molecular Formula: C20H16Br3ClN4O2

Molecular Weight: 619.54

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)c(Br)c14

Standard InChI:  InChI=1S/C20H16Br3ClN4O2/c1-18(2)11(24)7-19-8-5-13(29)27(19)4-3-12-20(18,26-17(30)25-12)28(19)10-6-9(21)15(22)16(23)14(8)10/h3-4,6,8,11H,5,7H2,1-2H3,(H,26,30)/t8-,11+,19+,20-/m1/s1

Standard InChI Key:  QAJAEFHWLZNVNF-KSALCITDSA-N

Molfile:  

     RDKit          2D

 31 36  0  0  0  0  0  0  0  0999 V2000
    9.0964   -6.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3741   -6.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5695   -7.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7539   -5.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4968   -5.7264    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.3741   -5.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804   -4.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0793   -5.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7295   -5.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7277   -4.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745   -4.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0855   -4.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2413   -4.8133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -4.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5196   -3.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904   -5.6626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5270   -5.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7279   -5.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986   -6.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1729   -6.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4573   -6.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9609   -7.0258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706   -7.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1157   -7.4933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7038   -3.7971    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8339   -3.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253   -3.5653    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4304   -4.3096    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4290   -5.8123    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.0809   -8.3923    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
 10 28  1  0
  7 29  1  0
  8 30  1  0
 24 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4169917

   ---

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: 619.54

Molecular Weight (Monoisotopic): 615.8512

AlogP: 5.23

#Rotatable Bonds: ┄

Polar Surface Area: 65.01

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.02

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 5.77

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.32

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