ID: ALA480099

Max Phase: Preclinical

Molecular Formula: C11H8O4

Molecular Weight: 204.18

Molecule Type: Small molecule

Representations

Synonyms (1): 2-Methoxyjuglone
Synonyms from Alternative Forms(1):

Canonical SMILES:  COC1=CC(=O)c2c(O)cccc2C1=O

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

Standard InChI Key:  GATGZQSBJAZYRT-UHFFFAOYSA-N

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

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: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.18

CX Basic pKa:

CX LogP: 1.43

CX LogD: 1.37

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.75

Np Likeness Score: 1.92

References

1. Kim SH, Lee KS, Son JK, Je GH, Lee JS, Lee CH, Cheong CJ..  (1998)  Cytotoxic compounds from the roots of Juglans mandshurica.,  61  (5): [PMID:9599266] [10.1021/np970413m]

2. 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]

3. Yu HY, Zhang XQ, Li X, Zeng FB, Ruan HL..  (2013)  2-methoxyjuglone induces apoptosis in HepG2 human hepatocellular carcinoma cells and exhibits in vivo antitumor activity in a H22 mouse hepatocellular carcinoma model.,  76  (5): [PMID:23597099] [10.1021/np400025b]

4. 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]

5. 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]

6. Li Q,Xu W,Fan R,Zhang J,Li Y,Wang X,Han S,Liu W,Pan M,Cheng Z.  (2020)  Penithoketone and Penithochromones A-L, Polyketides from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3.,  83  (9): [PMID:32902982] [10.1021/acs.jnatprod.0c00571]

Source

Source(1):

• Scientific Literature