Securamine E

ID: ALA4173439

PubChem CID: 10768809

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)cc(Br)c14

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

Standard InChI Key:  KEXODAJSSVPALY-WDFHTVOWSA-N

Molfile:  

     RDKit          2D

 30 35  0  0  0  0  0  0  0  0999 V2000
   10.5616  -14.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8434  -14.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0347  -15.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2190  -13.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9578  -13.9602    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8434  -13.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5703  -12.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5692  -13.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2153  -14.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2135  -12.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8561  -12.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8609  -13.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5630  -12.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7147  -13.0513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7076  -12.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9971  -12.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5680  -13.8964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0045  -13.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1972  -13.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1679  -14.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6463  -14.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9348  -14.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4426  -15.2555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8481  -15.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5892  -15.7189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1855  -12.0433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3032  -11.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2111  -11.8115    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.9231  -14.0461    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.5585  -16.6138    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
  8 29  1  0
 24 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4173439

   (1R,9R,19S,21S)-5,7-dibromo-21-chloro-20,20-dimethyl-2,12,16,18-tetrazahexacyclo[10.10.0.01,9.02,19.03,8.015,19]docosa-3(8),4,6,13,15-pentaene-11,17-dione

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: 0.57

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