(+)-Eleutherin

ID: ALA594153

Chembl Id: CHEMBL594153

Cas Number: 64869-73-4

PubChem CID: 10166

Max Phase: Preclinical

Molecular Formula: C16H16O4

Molecular Weight: 272.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-Eleutherin | Eleutherin|478-36-4|(+)-Eleutherin|BRN 0087122|(+/-)-Eleutherin|Eleutherin, (+/-)-|9J86WO1VYK|7FTP57M80A|CHEBI:4774|(1R,3S)-9-methoxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione|1H-Naphtho(2,3-c)pyran-5,10-dione, 3,4-dihydro-9-methoxy-1,3-dimethyl-, (1R-cis)-|64869-73-4|(1R,3S)-9-Methoxy-1,3-dimethyl-3,4-dihydro-1H-benzo(g)isochromene-5,10-dione|1H-Naphtho(2,3-C)pyran-5,10-dione, 3,4-dihydro-9-methoxy-1,3-dimethyl-, (1R,3S)-rel-|1H-Naphtho(2,3-C)pyran-5,10-dione, Show More⌵

Canonical SMILES:  COc1cccc2c1C(=O)C1=C(C[C@H](C)O[C@@H]1C)C2=O

Standard InChI:  InChI=1S/C16H16O4/c1-8-7-11-13(9(2)20-8)16(18)14-10(15(11)17)5-4-6-12(14)19-3/h4-6,8-9H,7H2,1-3H3/t8-,9+/m0/s1

Standard InChI Key:  IAJIIJBMBCZPSW-DTWKUNHWSA-N

Alternative Forms

1. Parent:

   

   ALA594153

   Eleutherin

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: 272.30

Molecular Weight (Monoisotopic): 272.1049

AlogP: 2.57

#Rotatable Bonds: 1

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.85

CX LogD: 1.85

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.79

Np Likeness Score: 1.50

References

1. Sperry J, Lorenzo-Castrillejo I, Brimble MA, Machín F..  (2009)  Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum.,  17  (20): [PMID:19783445] [10.1016/j.bmc.2009.08.064]

2. Heapy AM, Patterson AV, Smaill JB, Jamieson SM, Guise CP, Sperry J, Hume PA, Rathwell K, Brimble MA..  (2013)  Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions.,  21  (24): [PMID:24436995] [10.1016/j.bmc.2013.09.052]

Source

Source(1):

• Scientific Literature