2-Methyl-[1,4]benzoquinone

ID: ALA358225

Cas Number: 553-97-9

PubChem CID: 11122

Product Number: S66415, Order Now?

Max Phase: Preclinical

Molecular Formula: C7H6O2

Molecular Weight: 122.12

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Methyl-[1,4]Benzoquinone | p-Toluquinone|553-97-9|Methyl-p-benzoquinone|2-METHYL-1,4-BENZOQUINONE|2-methylcyclohexa-2,5-diene-1,4-dione|Toluquinone|Methyl-1,4-benzoquinone|2-Methylquinone|2-Methyl-p-benzoquinone|1,4-Toluquinone|Tolylquinone|2-Methylbenzoquinone|Methylbenzoquinone|p-Benzoquinone, 2-methyl-|Methylquinone|2,5-Cyclohexadiene-1,4-dione, 2-methyl-|2-Methyl-1,4-quinone|2-Methylbenzoquinone-1,4|1,4-Toluchinon|2-Methyl-2,5-cyclohexadiene-1,4-dione|2-Methyl-1,4-benzochinon|2-Methyl-[1,4Show More⌵

Canonical SMILES:  CC1=CC(=O)C=CC1=O

Standard InChI:  InChI=1S/C7H6O2/c1-5-4-6(8)2-3-7(5)9/h2-4H,1H3

Standard InChI Key:  VTWDKFNVVLAELH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

  9  9  0  0  0  0  0  0  0  0999 V2000
   -1.0258  -10.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0270  -11.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126  -12.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035  -11.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4006  -10.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3144  -10.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3168   -9.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128  -13.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130  -10.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  2  3  1  0
  5  6  1  0
  6  1  1  0
  1  2  2  0
  6  7  2  0
  3  4  1  0
  3  8  2  0
  5  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA358225

   Cresoquinone

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: 122.12

Molecular Weight (Monoisotopic): 122.0368

AlogP: 0.64

#Rotatable Bonds: ┄

Polar Surface Area: 34.14

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.42

CX LogD: 1.42

Aromatic Rings: ┄

Heavy Atoms: 9

QED Weighted: 0.44

Np Likeness Score: 1.71

References

1. Mayalarp SP, Hargreaves RH, Butler J, O'Hare CC, Hartley JA..  (1996)  Cross-linking and sequence specific alkylation of DNA BY aziridinylquinones. 1. Quinone methides.,  39  (2): [PMID:8558523] [10.1021/jm950629q]

2. Moret EE, de Boer M, Hilbers HW, Tollenaere JP, Janssen LH, Holthuis JJ, Driebergen RJ, Verboom W, Reinhoudt DN..  (1996)  In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.,  39  (3): [PMID:8576915] [10.1021/jm9405147]

3. Kumar S, Malachowski WP, DuHadaway JB, LaLonde JM, Carroll PJ, Jaller D, Metz R, Prendergast GC, Muller AJ..  (2008)  Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors.,  51  (6): [PMID:18318466] [10.1021/jm7014155]

4. De Rosa S, De Giulio A, Iodice C..  (1994)  Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.,  57  (12): [PMID:7714539] [10.1021/np50114a015]

5. Mozaina K, Cantrell CL, Mims AB, Lax AR, Tellez MR, Osbrink WL..  (2008)  Activity of 1,4-benzoquinones against formosan subterranean termites (Coptotermes formosanus).,  56  (11): [PMID:18461966] [10.1021/jf800331r]

6. Bremer PT, Hixon MS, Janda KD..  (2014)  Benzoquinones as inhibitors of botulinum neurotoxin serotype A.,  22  (15): [PMID:24984937] [10.1016/j.bmc.2014.06.004]

7. Johnson-Ajinwo OR, Ullah I, Mbye H, Richardson A, Horrocks P, Li WW..  (2018)  The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents.,  28  (7): [PMID:29519737] [10.1016/j.bmcl.2018.02.051]

8. Calil FA, David JS, Chiappetta ERC, Fumagalli F, Mello RB, Leite FHA, Castilho MS, Emery FS, Nonato MC..  (2019)  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.,  167  [PMID:30776695] [10.1016/j.ejmech.2019.02.018]

Source

Source(1):

• Scientific Literature