Fascaplysin

ID: ALA602937

Cas Number: 132911-47-8

PubChem CID: 73293

Product Number: F610280, Order Now?

Max Phase: Preclinical

Molecular Formula: C18H11N2O+

Molecular Weight: 271.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fascaplysin | GNF-PF-1458|CHEMBL602937|GTPL5969|SCHEMBL1728912|BDBM59087|CHEBI:93765|HSCI1_000331|NCGC00346951-01|BRD-K13287209-003-01-6|BRD-K13287209-003-02-4|BRD-K13287209-003-03-2|BRD-K13287209-311-01-3|BRD-K13287209-311-02-1|Q27077284|13-Oxo-4a,12,13,13a-tetrahydro-pyrido[1,2-a:3,4-b]diindol-5-ylium|3-aza-13-azoniapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1(13),2(10),4,6,8,11,14,16,18-nonaen-20-one

Synonyms from Alternative Forms(2): GNF-Pf-1458 | NSC-622398

Canonical SMILES:  O=C1c2ccccc2-[n+]2ccc3c([nH]c4ccccc43)c21

Standard InChI:  InChI=1S/C18H10N2O/c21-18-13-6-2-4-8-15(13)20-10-9-12-11-5-1-3-7-14(11)19-16(12)17(18)20/h1-10H/p+1

Standard InChI Key:  WYQIPCUPNMRAKP-UHFFFAOYSA-O

Molfile:  

     RDKit          2D

 21 25  0  0  0  0  0  0  0  0999 V2000
    0.7872    0.5178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3747   -0.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -0.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268   -0.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0023   -0.8097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942    0.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6804   -0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    0.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560   -0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3747    1.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697    0.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503    1.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552   -1.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4341   -0.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2616    0.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3372    0.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096   -0.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016   -0.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    0.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0908    0.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1771   -0.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7  6  1  0
  8  3  1  0
  9  5  1  0
  1 10  2  0
 11  8  1  0
 12 10  1  0
 13  4  2  0
  7 14  2  0
 15  6  2  0
 16 11  2  0
  9 17  2  0
 18 14  1  0
 19 15  1  0
 20 16  1  0
 21 17  1  0
 12  8  2  0
  7  4  1  0
 18 19  2  0
  9 11  1  0
 21 20  2  0
M  CHG  1   1   1
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA602937

   Fascaplysin

2. Parent:

   

   ALA602937

   fascaplysin
3. 

   ALA602937

   3-Aza-13-azoniapentacyclo[11.7.0.02,10.04,9.014,19]icosa-1(13),2(10),4,6,8,11,14,16,18-nonaen-20-one;bromide

Molecule Features

Natural Product: No

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: 271.30

Molecular Weight (Monoisotopic): 271.0866

AlogP: 3.14

#Rotatable Bonds: ┄

Polar Surface Area: 36.74

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.25

CX Basic pKa: ┄

CX LogP: 0.38

CX LogD: 0.38

Aromatic Rings: 4

Heavy Atoms: 21

QED Weighted: 0.43

Np Likeness Score: 1.19

References

1. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ..  (2013)  A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.,  451  (2): [PMID:23398362] [10.1042/bj20121418]

2. PubChem BioAssay data set, 

3. Bharate SB, Manda S, Joshi P, Singh B, Vishwakarma RA.  (2012)  Total synthesis and anti-cholinesterase activity of marine-derived bis-indole alkaloid fascaplysin,  3  (9): [10.1039/C2MD20076G]

4. Khokhar S, Feng Y, Campitelli MR, Ekins MG, Hooper JN, Beattie KD, Sadowski MC, Nelson CC, Davis RA..  (2014)  Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp.,  24  (15): [PMID:24973030] [10.1016/j.bmcl.2014.05.104]

5. Beato A, Gori A, Boucherle B, Peuchmaur M, Haudecoeur R..  (2021)  β-Carboline as a Privileged Scaffold for Multitarget Strategies in Alzheimer's Disease Therapy.,  64  (3.0): [PMID:33528252] [10.1021/acs.jmedchem.0c01887]

6. Luo B, Song X..  (2021)  A comprehensive overview of β-carbolines and its derivatives as anticancer agents.,  224  [PMID:34332400] [10.1016/j.ejmech.2021.113688]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays