3-methoxyjuglone

ID: ALA2204407

Cas Number: 15254-76-9

PubChem CID: 609303

Max Phase: Preclinical

Molecular Formula: C11H8O4

Molecular Weight: 204.18

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3-Methoxyjuglone | 8-hydroxy-2-methoxynaphthalene-1,4-dione|15254-76-9|1,4-Naphthalenedione, 8-hydroxy-2-methoxy-|8-Hydroxy-2-methoxy-1,4-naphthalenedione|1,4-Naphthoquinone, 8-hydroxy-2-methoxy-|3-Methoxyjuglone|8-Hydroxy-2-methoxy-1,4-naphthoquinone|SCHEMBL5174769|CHEMBL2204407|DTXSID90346065|HOFSOQDUZIZMBA-UHFFFAOYSA-N|8-Hydroxy-2-methoxynaphthoquinone #

Canonical SMILES:  COC1=CC(=O)c2cccc(O)c2C1=O

Standard InChI:  InChI=1S/C11H8O4/c1-15-9-5-8(13)6-3-2-4-7(12)10(6)11(9)14/h2-5,12H,1H3

Standard InChI Key:  HOFSOQDUZIZMBA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    1.0015  -21.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004  -22.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084  -22.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7066  -21.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4152  -21.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141  -22.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203  -22.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8321  -22.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8333  -21.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1226  -21.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1180  -23.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1226  -20.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7101  -23.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387  -22.8521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5364  -23.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  2  0
 10 12  2  0
  3 13  1  0
  8 14  1  0
 14 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2204407

   8-Hydroxy-2-methoxynaphthalene-1,4-dione

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: 204.18

Molecular Weight (Monoisotopic): 204.0423

AlogP: 1.30

#Rotatable Bonds: 1

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.09

CX Basic pKa: ┄

CX LogP: 1.43

CX LogD: 1.35

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.75

Np Likeness Score: 1.98

References

1. García A, Bocanegra-García V, Palma-Nicolás JP, Rivera G..  (2012)  Recent advances in antitubercular natural products.,  49  [PMID:22280816] [10.1016/j.ejmech.2011.12.029]

2. Pelageev DN, Dyshlovoy SA, Pokhilo ND, Denisenko VA, Borisova KL, Keller-von Amsberg G, Bokemeyer C, Fedorov SN, Honecker F, Anufriev VP..  (2014)  Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.,  77  [PMID:24631733] [10.1016/j.ejmech.2014.03.006]

3. Manickam M, Boggu PR, Cho J, Nam YJ, Lee SJ, Jung SH..  (2018)  Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity.,  28  (11): [PMID:29735338] [10.1016/j.bmcl.2018.04.060]

Source

Source(1):

• Scientific Literature