chetoseminudin B

ID: ALA512683

PubChem CID: 11211175

Max Phase: Preclinical

Molecular Formula: C17H21N3O3S2

Molecular Weight: 379.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS[C@]1(Cc2c[nH]c3ccccc23)NC(=O)[C@](CO)(SC)N(C)C1=O

Standard InChI:  InChI=1S/C17H21N3O3S2/c1-20-15(23)16(24-2,19-14(22)17(20,10-21)25-3)8-11-9-18-13-7-5-4-6-12(11)13/h4-7,9,18,21H,8,10H2,1-3H3,(H,19,22)/t16-,17-/m0/s1

Standard InChI Key:  CCPHAMSKHBDMDS-IRXDYDNUSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   13.8508  -10.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0302   -9.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8514   -9.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1853  -10.4675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0003  -10.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4928   -9.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1676   -9.1425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3411   -9.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6568   -8.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0090   -8.2874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3255  -11.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4380   -8.9879    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.6122   -8.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9023  -10.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7280  -10.6119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0718   -9.3139    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.8711   -9.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9842  -11.9312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4042  -11.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1764  -11.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0986  -10.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3507  -10.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6801  -11.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7622  -11.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5103  -12.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  8  1  0
 12 13  1  0
  4  5  1  0
  6 14  1  0
  5  6  1  0
 14 15  1  0
  6  7  1  0
  6 16  1  1
  7  8  1  0
 16 17  1  0
  1 21  1  0
  2  1  1  0
  7  9  1  0
 20 18  1  0
 18 19  1  0
 19  1  2  0
  3  4  1  0
  8 10  2  0
 20 21  2  0
 21 22  1  0
  5 11  2  0
 22 23  2  0
  3  2  1  0
 23 24  1  0
  3 12  1  1
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA512683

   CHETOSEMINUDIN B

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: 379.51

Molecular Weight (Monoisotopic): 379.1024

AlogP: 1.41

#Rotatable Bonds: 5

Polar Surface Area: 85.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.58

CX Basic pKa: ┄

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: 1.34

References

1. Fujimoto H, Sumino M, Okuyama E, Ishibashi M..  (2004)  Immunomodulatory constituents from an Ascomycete, Chaetomium seminudum.,  67  (1): [PMID:14738397] [10.1021/np0302201]

2. Watts KR, Ratnam J, Ang KH, Tenney K, Compton JE, McKerrow J, Crews P..  (2010)  Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi.,  18  (7): [PMID:20303767] [10.1016/j.bmc.2010.02.034]

3. Wang FZ, Huang Z, Shi XF, Chen YC, Zhang WM, Tian XP, Li J, Zhang S..  (2012)  Cytotoxic indole diketopiperazines from the deep sea-derived fungus Acrostalagmus luteoalbus SCSIO F457.,  22  (23): [PMID:23079524] [10.1016/j.bmcl.2012.08.115]

4. Zhai YJ, Huo GM, Zhang Q, Li D, Wang DC, Qi JZ, Han WB, Gao JM..  (2020)  Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an Endophytic Phaeosphaeria fuckelii.,  83  (5): [PMID:32342692] [10.1021/acs.jnatprod.0c00046]

Source

Source(1):

• Scientific Literature