Fostularin 2

ID: ALA2332122

PubChem CID: 71716961

Max Phase: Preclinical

Molecular Formula: C22H21Br4N3O8

Molecular Weight: 775.04

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fostularin 2 | Fostularin 2|CHEMBL2332122

Canonical SMILES:  COC1=C(Br)[C@H](O)[C@@]2(C=C1Br)CC(C(=O)NCC(O)c1cc(Br)c(OC[C@H]3CNC(=O)O3)c(Br)c1)=NO2

Standard InChI:  InChI=1S/C22H21Br4N3O8/c1-34-18-13(25)4-22(19(31)16(18)26)5-14(29-37-22)20(32)27-7-15(30)9-2-11(23)17(12(24)3-9)35-8-10-6-28-21(33)36-10/h2-4,10,15,19,30-31H,5-8H2,1H3,(H,27,32)(H,28,33)/t10-,15?,19+,22-/m1/s1

Standard InChI Key:  WKUSHGVKGFQCSJ-VGDKHQHMSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    3.4534   -9.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7804   -9.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0240  -10.5572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8516  -10.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1187   -9.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468   -8.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468   -8.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -8.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -8.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -7.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8875   -7.6447    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -7.6447    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -6.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1725   -6.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312   -9.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3258  -11.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824  -11.9941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1476  -11.1699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6260  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4477  -11.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9220  -12.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7911  -11.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5749  -13.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0484  -13.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8710  -13.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2138  -13.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7384  -12.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0354  -12.9571    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.7006  -14.6123    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.3462  -14.4630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1678  -14.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6470  -15.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3834  -15.8379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0429  -16.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7175  -15.8527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4734  -15.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0338  -17.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  6 10  2  0
  7  1  1  0
  1  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
  6 12  1  0
 10 13  1  0
 13 14  1  0
  7 15  1  1
  4 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 26 28  1  0
 24 29  1  0
 25 30  1  0
 30 31  1  0
 32 31  1  1
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 32  1  0
 34 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332122

   FOSTULARIN 2

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: 775.04

Molecular Weight (Monoisotopic): 770.8062

AlogP: 3.27

#Rotatable Bonds: 8

Polar Surface Area: 147.94

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.52

CX Basic pKa: ┄

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.32

Np Likeness Score: 1.61

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