Cephalochromin

ID: ALA463175

Chembl Id: CHEMBL463175

Cas Number: 25908-26-3

PubChem CID: 160115

Max Phase: Preclinical

Molecular Formula: C28H22O10

Molecular Weight: 518.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cephalochromin | Cephalochromin|25908-26-3|Sch-45752|5,6,8-trihydroxy-2-methyl-9-(5,6,8-trihydroxy-2-methyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl)-2,3-dihydrobenzo[g]chromen-4-one|MLS000876993|CHEMBL463175|NSC201419|NSC627953|SMR000440611|Sch 45752|Compound NP-004604|cid_160115|MEGxm0_000312|SCHEMBL1111561|ACon0_000585|ACon1_000126|DTXSID60948813|CHEBI:181037|HMS2270H11|BDBM50269745|HB3825|AKOS040739787|NSC-201419|NSC-627953|NCGC00180856-01|NS00097065|SR-01000758207|SR-01000758207-2|2,2',3,3'-TeShow More⌵

Canonical SMILES:  CC1CC(=O)c2c(cc3c(-c4c(O)cc(O)c5c(O)c6c(cc45)OC(C)CC6=O)c(O)cc(O)c3c2O)O1

Standard InChI:  InChI=1S/C28H22O10/c1-9-3-13(29)25-19(37-9)5-11-21(15(31)7-17(33)23(11)27(25)35)22-12-6-20-26(14(30)4-10(2)38-20)28(36)24(12)18(34)8-16(22)32/h5-10,31-36H,3-4H2,1-2H3

Standard InChI Key:  JGQBYBXYRUCBQY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA463175

   CEPHALOCHROMIN

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: 518.47

Molecular Weight (Monoisotopic): 518.1213

AlogP: 4.60

#Rotatable Bonds: 1

Polar Surface Area: 173.98

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.49

CX Basic pKa:

CX LogP: 4.59

CX LogD: 4.28

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.21

Np Likeness Score: 1.10

References

1. Potterat O, Wagner K, Gemmecker G, Mack J, Puder C, Vettermann R, Streicher R..  (2004)  BI-32169, a bicyclic 19-peptide with strong glucagon receptor antagonist activity from Streptomyces sp.,  67  (9): [PMID:15387654] [10.1021/np040093o]

2. PubChem BioAssay data set, 

3. Cardellina JH, Roxas-Duncan VI, Montgomery V, Eccard V, Campbell Y, Hu X, Khavrutskii I, Tawa GJ, Wallqvist A, Gloer JB, Phatak NL, Höller U, Soman AG, Joshi BK, Hein SM, Wicklow DT, Smith LA..  (2012)  Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.,  3  (5): [PMID:24900483] [10.1021/ml200312s]

4. Hsiao CJ, Hsiao G, Chen WL, Wang SW, Chiang CP, Liu LY, Guh JH, Lee TH, Chung CL..  (2014)  Cephalochromin induces G0/G1 cell cycle arrest and apoptosis in A549 human non-small-cell lung cancer cells by inflicting mitochondrial disruption.,  77  (4): [PMID:24588135] [10.1021/np400517g]

5. Rana P, Ghouse SM, Akunuri R, Madhavi YV, Chopra S, Nanduri S..  (2020)  FabI (enoyl acyl carrier protein reductase) - A potential broad spectrum therapeutic target and its inhibitors.,  208  [PMID:32883635] [10.1016/j.ejmech.2020.112757]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays