N-(7-(dimethylamino)-2-hexadecyl-3H-phenothiazin-3-ylidene)-N-methylmethanaminium iodide

ID: ALA4129965

Chembl Id: CHEMBL4129965

PubChem CID: 145962257

Max Phase: Preclinical

Molecular Formula: C32H50IN3S

Molecular Weight: 508.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCc1cc2nc3ccc(N(C)C)cc3sc-2cc1=[N+](C)C.[I-]

Standard InChI:  InChI=1S/C32H50N3S.HI/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23-29-32(25-30(26)35(4)5)36-31-24-27(34(2)3)21-22-28(31)33-29;/h21-25H,6-20H2,1-5H3;1H/q+1;/p-1

Standard InChI Key:  PQCSJALMHHZARC-UHFFFAOYSA-M

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: 508.84

Molecular Weight (Monoisotopic): 508.3720

AlogP: 8.52

#Rotatable Bonds: 16

Polar Surface Area: 19.14

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 3.12

CX LogP: 6.44

CX LogD: 6.44

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.11

Np Likeness Score: -0.70

References

1. Khdour OM, Bandyopadhyay I, Chowdhury SR, Visavadiya NP, Hecht SM..  (2018)  Lipophilic methylene blue analogues enhance mitochondrial function and increase frataxin levels in a cellular model of Friedreich's ataxia.,  26  (12): [PMID:29773347] [10.1016/j.bmc.2018.05.005]

2. Khdour OM, Bandyopadhyay I, Visavadiya NP, Roy Chowdhury S, Hecht SM..  (2018)  Phenothiazine antioxidants increase mitochondrial biogenesis and frataxin levels in Friedreich's ataxia cells.,  9  (9): [PMID:30288223] [10.1039/C8MD00274F]

3. Liu J,Bandyopadhyay I,Zheng L,Khdour OM,Hecht SM.  (2020)  Antiferroptotic Activity of Phenothiazine Analogues: A Novel Therapeutic Strategy for Oxidative Stress Related Disease.,  11  (11): [PMID:33214825] [10.1021/acsmedchemlett.0c00293]

Source

Source(1):

• Scientific Literature