(+)-Pseudoceralidinone A

ID: ALA2332124

PubChem CID: 71665142

Max Phase: Preclinical

Molecular Formula: C14H18Br2N2O3

Molecular Weight: 422.12

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-Pseudoceralidinone A | (+)-Pseudoceralidinone A|CHEMBL2332124

Canonical SMILES:  CN(C)CCCOc1c(Br)cc([C@H]2CNC(=O)O2)cc1Br

Standard InChI:  InChI=1S/C14H18Br2N2O3/c1-18(2)4-3-5-20-13-10(15)6-9(7-11(13)16)12-8-17-14(19)21-12/h6-7,12H,3-5,8H2,1-2H3,(H,17,19)/t12-/m1/s1

Standard InChI Key:  ZNFKPSPBLHQVEJ-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    6.0819   -2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0808   -3.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7956   -3.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5121   -3.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5092   -2.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7938   -1.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7913   -1.0331    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.3660   -3.5102    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.3673   -1.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530   -2.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384   -1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2240   -2.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5095   -1.8592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951   -2.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5093   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2231   -3.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3107   -4.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1180   -4.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5294   -3.7825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9762   -3.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4547   -5.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  2  8  1  0
  1  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 16  4  1  1
 18 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332124

   (+)-Pseudoceralidinone A

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: 422.12

Molecular Weight (Monoisotopic): 419.9684

AlogP: 3.32

#Rotatable Bonds: 6

Polar Surface Area: 50.80

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.81

CX Basic pKa: 9.26

CX LogP: 2.88

CX LogD: 1.03

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: 0.43

References

1. Tran TD, Pham NB, Fechner G, Hooper JN, Quinn RJ..  (2013)  Bromotyrosine alkaloids from the Australian marine sponge Pseudoceratina verrucosa.,  76  (4): [PMID:23489291] [10.1021/np300648d]

Source

Source(1):

• Scientific Literature