Sceptrin

ID: ALA307456

Chembl Id: CHEMBL307456

Cas Number: 79638-16-7

PubChem CID: 157394

Max Phase: Preclinical

Molecular Formula: C22H24Br2N10O2

Molecular Weight: 620.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Sceptrin | Sceptrin|79638-16-7|CHEBI:80954|CHEMBL307456|DTXSID00276460|C17166|Q15424768

Synonyms from Alternative Forms(2): Sceptrin (TFA salt) | Sceptrin (HCl)

Canonical SMILES:  Nc1nc([C@H]2[C@H](CNC(=O)c3cc(Br)c[nH]3)[C@@H](CNC(=O)c3cc(Br)c[nH]3)[C@@H]2c2c[nH]c(N)n2)c[nH]1

Standard InChI:  InChI=1S/C22H24Br2N10O2/c23-9-1-13(27-3-9)19(35)29-5-11-12(6-30-20(36)14-2-10(24)4-28-14)18(16-8-32-22(26)34-16)17(11)15-7-31-21(25)33-15/h1-4,7-8,11-12,17-18,27-28H,5-6H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t11-,12-,17-,18-/m1/s1

Standard InChI Key:  YPZNLFZLPZWWAD-GWIYSAMLSA-N

Alternative Forms

1. Parent:

   

   ALA307456

   SCEPTRIN

2. Alternative Forms:

   

   ALA307456

   SCEPTRIN (TFA SALT)
3. 

   ALA307456

   Sceptrin dihydrochloride

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: 620.31

Molecular Weight (Monoisotopic): 618.0450

AlogP: 2.45

#Rotatable Bonds: 8

Polar Surface Area: 199.18

Molecular Species: BASE

HBA: 6

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 13.20

CX Basic pKa: 9.16

CX LogP: 0.88

CX LogD: -1.54

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.15

Np Likeness Score: 0.29

References

1. Cafieri F, Carnuccio R, Fattorusso E, Taglialatela-Scafati O, Vallefuoco T.  (1997)  Anti-histaminic activity of bromopyrrole alkaloids isolated from Caribbean Agelas sponges,  7  (17): [10.1016/S0960-894X(97)00415-0]

2. Mohammed R, Peng J, Kelly M, Hamann MT..  (2006)  Cyclic heptapeptides from the Jamaican sponge Stylissa caribica.,  69  (12): [PMID:17190452] [10.1021/np060006n]

3. Gao J, Caballero-George C, Wang B, Rao KV, Shilabin AG, Hamann MT..  (2009)  5-OHKF and NorKA, depsipeptides from a Hawaiian collection of Bryopsis pennata: binding properties for NorKA to the human neuropeptide Y Y1 receptor.,  72  (12): [PMID:19916528] [10.1021/np900287e]

4. Tilvi S, Moriou C, Martin MT, Gallard JF, Sorres J, Patel K, Petek S, Debitus C, Ermolenko L, Al-Mourabit A..  (2010)  Agelastatin E, agelastatin F, and benzosceptrin C from the marine sponge Agelas dendromorpha.,  73  (4): [PMID:20166736] [10.1021/np900539j]

5. Mahamed S, Motal R, Govender T, Dlamini N, Khuboni K, Hadeb Z, Shaik BB, Moodley K, Balaso Mohite S, Karpoormath R..  (2023)  A concise review on marine bromopyrrole alkaloids as anticancer agents.,  80  [PMID:36496202] [10.1016/j.bmcl.2022.129102]

6. Cockram PE, Smith TK..  (2018)  Active Natural Product Scaffolds against Trypanosomatid Parasites: A Review.,  81  (9): [PMID:30234295] [10.1021/acs.jnatprod.8b00159]

Source

Source(1):

• Scientific Literature