Securamine J

ID: ALA4176797

PubChem CID: 145975975

Max Phase: Preclinical

Molecular Formula: C21H21Br2ClN4O4

Molecular Weight: 588.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1[C@H](O)C2=NC(=O)N[C@@]23N2c4cc(Br)c(Br)cc4[C@H]4CC(=O)N1[C@]42C[C@H](Cl)C3(C)C

Standard InChI:  InChI=1S/C21H21Br2ClN4O4/c1-19(2)13(24)7-20-9-5-14(29)27(20)17(32-3)15(30)16-21(19,26-18(31)25-16)28(20)12-6-11(23)10(22)4-8(9)12/h4,6,9,13,15,17,30H,5,7H2,1-3H3,(H,26,31)/t9-,13+,15-,17+,20+,21-/m1/s1

Standard InChI Key:  XVYPXKFXSVSWCE-RFUHDIGYSA-N

Molfile:  

     RDKit          2D

 33 38  0  0  0  0  0  0  0  0999 V2000
   25.6257   -5.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9020   -5.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0976   -6.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2831   -5.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0276   -5.1280    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.9020   -4.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6124   -4.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6146   -4.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2593   -5.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2563   -3.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9061   -4.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9100   -4.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6152   -3.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7716   -4.2134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7638   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0529   -3.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6193   -5.0626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0569   -4.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2570   -4.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2287   -5.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7027   -6.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9860   -5.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4924   -6.4265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8989   -7.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6443   -6.8952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2349   -3.1993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.3639   -3.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9612   -3.7116    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   19.9630   -5.2136    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   22.6117   -7.7918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5069   -5.0529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6091   -4.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3801   -4.0291    0.0000 C   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  1  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
 20 31  1  6
 19 32  1  1
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4176797

   ---

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: 588.68

Molecular Weight (Monoisotopic): 585.9618

AlogP: 3.29

#Rotatable Bonds: 1

Polar Surface Area: 94.47

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.45

CX Basic pKa: ┄

CX LogP: 4.36

CX LogD: 4.36

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: 0.89

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