Securamine C

ID: ALA4166172

PubChem CID: 10766447

Max Phase: Preclinical

Molecular Formula: C20H18BrClN4O2

Molecular Weight: 461.75

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)ccc14

Standard InChI:  InChI=1S/C20H18BrClN4O2/c1-18(2)14(22)9-19-12-8-16(27)25(19)6-5-15-20(18,24-17(28)23-15)26(19)13-7-10(21)3-4-11(12)13/h3-7,12,14H,8-9H2,1-2H3,(H,24,28)/t12-,14+,19+,20-/m1/s1

Standard InChI Key:  JEVYNKSHGQMDPV-QTRFMYMGSA-N

Molfile:  

     RDKit          2D

 29 34  0  0  0  0  0  0  0  0999 V2000
   34.4582   -6.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7401   -6.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9313   -6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1157   -5.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8544   -5.4540    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.7401   -4.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4670   -4.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4659   -5.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1120   -5.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1102   -4.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7528   -4.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7576   -5.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4597   -4.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6114   -4.5492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6043   -3.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8938   -3.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4646   -5.3902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9012   -4.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0938   -5.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0645   -5.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5430   -6.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8315   -6.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3392   -6.7493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7448   -7.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4858   -7.2126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0822   -3.5370    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.1998   -3.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8197   -5.5399    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   31.4551   -8.1075    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
  8 28  1  0
 24 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4166172

   (1R,9R,19S,21S)-5-bromo-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: 461.75

Molecular Weight (Monoisotopic): 460.0302

AlogP: 3.71

#Rotatable Bonds: ┄

Polar Surface Area: 65.01

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.79

CX Basic pKa: 0.45

CX LogP: 4.24

CX LogD: 4.24

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: 0.56

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