5-Hydroxy-7-methyl-[1,4]naphthoquinone

ID: ALA430853

Chembl Id: CHEMBL430853

Cas Number: 14787-38-3

PubChem CID: 26905

Max Phase: Preclinical

Molecular Formula: C11H8O3

Molecular Weight: 188.18

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 7-Methyljuglone | Ramentaceone | 7-Methyljuglone|Ramentaceone|14787-38-3|5-hydroxy-7-methylnaphthalene-1,4-dione|7-Methyljuglon|JUGLONE, 7-METHYL-|5-Hydroxy-7-methyl-1,4-naphthoquinone|5-Hydroxy-7-methyl-1,4-naphthalenedione|1,4-Naphthalenedione, 5-hydroxy-7-methyl-|NSC208733|ZS3RW9P6DY|1,4-NAPHTHOQUINONE, 5-HYDROXY-7-METHYL-|5-Hydroxy-7-methyl-2,3-dihydronaphthal-ene-1,4-dione|CHEBI:8773|CHEMBL430853|4-08-00-02374 (Beilstein Handbook Reference)|NSC624625|NSC-208733|NSC-624625|5-hydroxy-7-methylShow More⌵

Canonical SMILES:  Cc1cc(O)c2c(c1)C(=O)C=CC2=O

Standard InChI:  InChI=1S/C11H8O3/c1-6-4-7-8(12)2-3-9(13)11(7)10(14)5-6/h2-5,14H,1H3

Standard InChI Key:  OZUSCVSONBBWOR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA430853

   RAMENTACEONE

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: 188.18

Molecular Weight (Monoisotopic): 188.0473

AlogP: 1.64

#Rotatable Bonds: ┄

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.40

CX Basic pKa: ┄

CX LogP: 2.35

CX LogD: 2.31

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.67

Np Likeness Score: 1.43

References

1. Singh SB, Graham PL, Reamer RA, Cordingley MG..  (2001)  Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues.,  11  (24): [PMID:11720861] [10.1016/s0960-894x(01)00648-5]

2. Mahapatra A, Mativandlela SP, Binneman B, Fourie PB, Hamilton CJ, Meyer JJ, van der Kooy F, Houghton P, Lall N..  (2007)  Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase.,  15  (24): [PMID:17888665] [10.1016/j.bmc.2007.08.064]

3. Gu JQ, Graf TN, Lee D, Chai HB, Mi Q, Kardono LB, Setyowati FM, Ismail R, Riswan S, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kroll DJ, Falkinham JO, Wall ME, Wani MC, Kinghorn AD, Oberlies NH..  (2004)  Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia.,  67  (7): [PMID:15270571] [10.1021/np040027m]

4. Kawiak A, Zawacka-Pankau J, Wasilewska A, Stasilojc G, Bigda J, Lojkowska E..  (2012)  Induction of apoptosis in HL-60 cells through the ROS-mediated mitochondrial pathway by ramentaceone from Drosera aliciae.,  75  (1): [PMID:22250825] [10.1021/np200247g]

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. 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]

8. Sharma R, Panigrahi D, Mishra GP.  (2012)  QSAR studies of 7-methyljuglone derivatives as antitubercular agents,  21  (8): [10.1007/s00044-011-9731-0]

9. Kishore N, Binneman B, Mahapatra A, van de Venter M, du Plessis-Stoman D, Boukes G, Houghton P, Marion Meyer JJ, Lall N..  (2014)  Cytotoxicity of synthesized 1,4-naphthoquinone analogues on selected human cancer cell lines.,  22  (17): [PMID:25059501] [10.1016/j.bmc.2014.06.013]

10. Schroeder RL, Goyal N, Bratton M, Townley I, Pham NA, Tram P, Stone T, Geathers J, Nguyen K, Sridhar J..  (2016)  Identification of quinones as novel PIM1 kinase inhibitors.,  26  (13): [PMID:27173800] [10.1016/j.bmcl.2016.04.079]

11. Chaudhari K, Surana S, Jain P, Patel HM..  (2016)  Mycobacterium Tuberculosis (MTB) GyrB inhibitors: An attractive approach for developing novel drugs against TB.,  124  [PMID:27569197] [10.1016/j.ejmech.2016.08.034]

12. Ahenkorah S, Coertzen D, Tong JX, Fridianto K, Wittlin S, Birkholtz LM, Tan KSW, Lam Y, Go ML, Haynes RK..  (2020)  Antimalarial N ¹,N ³-Dialkyldioxonaphthoimidazoliums: Synthesis, Biological Activity, and Structure-activity Relationships.,  11  (1): [PMID:31938463] [10.1021/acsmedchemlett.9b00457]

13. Pullella GA,Vuong D,Lacey E,Piggott MJ.  (2020)  Total Synthesis of the Antitumor-Antitubercular 2,6'-Bijuglone Natural Product Diospyrin and Its 3,6'-Isomer.,  83  (12.0): [PMID:33314932] [10.1021/acs.jnatprod.0c00800]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays