lissoclibadin 4

ID: ALA220033

PubChem CID: 16116092

Max Phase: Preclinical

Molecular Formula: C22H30N2O4S3

Molecular Weight: 482.69

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lissoclibadin 4 | lissoclibadin 4|CHEMBL220033

Canonical SMILES:  COc1cc(CCN(C)C)c2sc3c(O)c(OC)cc(CCN(C)C)c3ssc2c1O

Standard InChI:  InChI=1S/C22H30N2O4S3/c1-23(2)9-7-13-11-16(28-6)18(26)22-19(13)29-21-17(25)15(27-5)12-14(8-10-24(3)4)20(21)30-31-22/h11-12,25-26H,7-10H2,1-6H3

Standard InChI Key:  KVGFSMRBTDAHMD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.9180    0.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1736   -0.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1754    1.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335    0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324   -0.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923   -0.7506    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7684    1.1133    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708    0.9024    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9904   -0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -1.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2321   -1.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6025   -0.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1710    0.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    1.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6591    1.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4000    0.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1710   -1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9147   -1.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9121   -2.8319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518   -3.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656   -3.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275   -1.9671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635   -1.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2975   -2.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5347    0.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1039    1.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4677    2.2303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411    2.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2621    2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 15 10  1  0
  5  6  1  0
  4 16  1  0
  6  7  1  0
  1 17  1  0
  5  8  1  0
 17 18  1  0
  9 10  1  0
  3 19  1  0
 11  7  1  0
 19 20  1  0
  8  9  1  0
 20 21  1  0
  4  1  1  0
 21 22  1  0
 21 23  1  0
 10 11  2  0
 12 24  1  0
  2  3  1  0
 13 25  1  0
 11 12  1  0
 25 26  1  0
  3  6  2  0
 15 27  1  0
 12 13  2  0
 27 28  1  0
  1  2  2  0
 28 29  1  0
 13 14  1  0
 29 30  1  0
  5  4  2  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA220033

   LISSOCLIBADIN 4

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: 482.69

Molecular Weight (Monoisotopic): 482.1368

AlogP: 4.94

#Rotatable Bonds: 8

Polar Surface Area: 65.40

Molecular Species: BASE

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.90

CX Basic pKa: 9.69

CX LogP: 2.07

CX LogD: 0.53

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: 0.51

References

1. Nakazawa T, Xu J, Nishikawa T, Oda T, Fujita A, Ukai K, Mangindaan RE, Rotinsulu H, Kobayashi H, Namikoshi M..  (2007)  Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium.,  70  (3): [PMID:17269824] [10.1021/np060593c]

2. Tatsuta T, Hosono M, Rotinsulu H, Wewengkang DS, Sumilat DA, Namikoshi M, Yamazaki H..  (2017)  Lissoclibadin 1, a Polysulfur Aromatic Alkaloid from the Indonesian Ascidian Lissoclinum cf. badium, Induces Caspase-Dependent Apoptosis in Human Colon Cancer Cells and Suppresses Tumor Growth in Nude Mice.,  80  (2): [PMID:28181805] [10.1021/acs.jnatprod.6b01051]

3. Davison EK, Sperry J..  (2017)  Natural Products with Heteroatom-Rich Ring Systems.,  80  (11): [PMID:29135244] [10.1021/acs.jnatprod.7b00575]

Source

Source(1):

• Scientific Literature