5-O-{(Z)-Octadecenoyloxy}-1,4-naphthoquinone

ID: ALA1917198

Chembl Id: CHEMBL1917198

PubChem CID: 54597679

Max Phase: Preclinical

Molecular Formula: C28H38O4

Molecular Weight: 438.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC/C=C\CCCCCCCC(=O)Oc1cccc2c1C(=O)C=CC2=O

Standard InChI:  InChI=1S/C28H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-27(31)32-26-19-17-18-23-24(29)21-22-25(30)28(23)26/h9-10,17-19,21-22H,2-8,11-16,20H2,1H3/b10-9-

Standard InChI Key:  TUNHCPZKNYPWTH-KTKRTIGZSA-N

Alternative Forms

1. Parent:

   

   ALA1917198

   (5,8-dioxonaphthalen-1-yl) (Z)-octadec-9-enoate

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: 438.61

Molecular Weight (Monoisotopic): 438.2770

AlogP: 7.56

#Rotatable Bonds: 16

Polar Surface Area: 60.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 8.11

CX LogD: 8.11

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.12

Np Likeness Score: 0.77

References

1. Maruo S, Kuriyama I, Kuramochi K, Tsubaki K, Yoshida H, Mizushina Y..  (2011)  Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response.,  19  (19): [PMID:21903399] [10.1016/j.bmc.2011.08.023]

2. Fiorito S, Genovese S, Taddeo VA, Mathieu V, Kiss R, Epifano F..  (2016)  Novel juglone and plumbagin 5-O derivatives and their in vitro growth inhibitory activity against apoptosis-resistant cancer cells.,  26  (2): [PMID:26706169] [10.1016/j.bmcl.2015.12.017]

Source

Source(1):

• Scientific Literature