NP-MRD: Showing NP-Card for 2-Methyl-1,4-napthoquinone (NP0331764)

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Record Information

Version

1.0

Created at

2023-08-14 16:00:29 UTC

Updated at

2024-04-19 09:51:48 UTC

NP-MRD ID

NP0331764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Methyl-1,4-napthoquinone

Description

Menadione, also known as vitamin K3 or aquinone, belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Menadione is an extremely weak basic (essentially neutral) compound (based on its pKa). Menadione exists in all living organisms, ranging from bacteria to humans. In humans, menadione is involved in doxorubicin metabolism pathway. Outside of the human body, Menadione has been detected, but not quantified in, several different foods, such as wax gourds, garden rhubarbs, common buckwheats, chinese chives, and figs. This could make menadione a potential biomarker for the consumption of these foods. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin. Menadione is a potentially toxic compound. Moreover, menadione supplements have been banned by the FDA because of their high toxicity. Large doses have also been reported to cause brain damage. Menadione is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. It was first documented in 1961 (PMID: 13779073). Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement (PMID: 16140270) (PMID: 12895502) (PMID: 1857739) (PMID: 9728483) (PMID: 15265851) (PMID: 12665684).

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 170                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       5.747  -3.080   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.747   3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.080  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.080   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.413  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.413   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.457  -1.593   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.457   1.593   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.852  -0.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.852   0.802   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    4    6    9                                                  
CONECT    4    3    7   10                                                  
CONECT    5    6    8   11                                                  
CONECT    6    1    3    5                                                  
CONECT    7    2    4    8                                                  
CONECT    8    5    7                                                       
CONECT    9    3   12                                                       
CONECT   10    4   13                                                       
CONECT   11    5                                                            
CONECT   12    9   13                                                       
CONECT   13   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-Methyl-1,4-naphthalenedione	ChEBI
2-Methyl-1,4-naphthochinon	ChEBI
2-Methyl-1,4-naphthoquinone	ChEBI
Vitamin K3	ChEBI
Kappaxin	Kegg
2-Methyl-1,4-naftochinon	HMDB
2-Methyl-1,4-naphthalendione	HMDB
2-Methyl-1,4-naphthodione	HMDB
2-Methylnaphthoquinone	HMDB
3-Methyl-1,4-naphthoquinone	HMDB
Aquakay	HMDB
Aquinone	HMDB
Hemodal	HMDB
Juva-K	HMDB
K-Thrombyl	HMDB
K-Vitan	HMDB
Kaergona	HMDB
Kanone	HMDB
Kappaxan	HMDB
Karcon	HMDB
Kareon	HMDB
Kativ-g	HMDB
Kayklot	HMDB
Kaykot	HMDB
Kaynone	HMDB
Kayquinone	HMDB
Kipca	HMDB
Kipca-oil soluble	HMDB
Klottone	HMDB
Koaxin	HMDB
Kolklot	HMDB
Menadion	HMDB
Menaphthene	HMDB
Menaphthon	HMDB
Menaphthone	HMDB
Menaphtone	HMDB
Menaquinone	HMDB
Menaquinone O	HMDB
Mitenon	HMDB
Mitenone	HMDB
MNQ	HMDB
Panosine	HMDB
Prokayvit	HMDB
Synkay	HMDB
Thyloquinone	HMDB
Vitamin K0	HMDB
Vitamin K2	HMDB
Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene	HMDB
Bisulfite, menadione	HMDB
Vicasol	HMDB
Bisulfite, menadione sodium	HMDB
Menadione sodium bisulfite	HMDB
Vikasol	HMDB
Vitamin K 3	HMDB
Menadione sodium bisulfite, trihydrate	HMDB
Vitamin K3 sodium bisulfite	HMDB
Menadione bisulfite	HMDB
Sodium bisulfite, menadione	HMDB

Chemical Formula

C₁₁H₈O₂

Average Mass

172.1800 Da

Monoisotopic Mass

172.05243 Da

IUPAC Name

2-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional Name

menadione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

InChI Key

MJVAVZPDRWSRRC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-06	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-06	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-14	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:28869 )
vitamin K (C05377 )
Fat-soluble vitamins (C05377 )
a vitamin K (CPD-3766 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.91	ALOGPS
logP	1.89	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.94	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.54 m³·mol⁻¹	ChemAxon
Polarizability	17.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001892

DrugBank ID

DB00170

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000953

KNApSAcK ID

Not Available

Chemspider ID

3915

KEGG Compound ID

C05377

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Menadione

METLIN ID

3910

PubChem Compound

4055

PDB ID

Not Available

ChEBI ID

28869

Good Scents ID

Not Available

References

General References

Kwasnicka-Crawford DA, Vincent SR: Role of a novel dual flavin reductase (NR1) and an associated histidine triad protein (DCS-1) in menadione-induced cytotoxicity. Biochem Biophys Res Commun. 2005 Oct 21;336(2):565-71. [PubMed:16140270 ]
Snider BJ, Moss JL, Revilla FJ, Lee CS, Wheeler VC, Macdonald ME, Choi DW: Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Neuroscience. 2003;120(3):617-25. [PubMed:12895502 ]
Robertson DG, Bailey DL, Martin RA: Species differences in response to photohemolytic agents. Photochem Photobiol. 1991 Apr;53(4):455-61. [PubMed:1857739 ]
Chladek J, Martinkova J, Sispera L: An in vitro study on methotrexate hydroxylation in rat and human liver. Physiol Res. 1997;46(5):371-9. [PubMed:9728483 ]
Habu D, Shiomi S, Tamori A, Takeda T, Tanaka T, Kubo S, Nishiguchi S: Role of vitamin K2 in the development of hepatocellular carcinoma in women with viral cirrhosis of the liver. JAMA. 2004 Jul 21;292(3):358-61. [PubMed:15265851 ]
Lasalvia-Prisco E, Cucchi S, Vazquez J, Lasalvia-Galante E, Golomar W, Gordon W: Serum markers variation consistent with autoschizis induced by ascorbic acid-menadione in patients with prostate cancer. Med Oncol. 2003;20(1):45-52. [PubMed:12665684 ]
Harrington DJ, Soper R, Edwards C, Savidge GF, Hodges SJ, Shearer MJ: Determination of the urinary aglycone metabolites of vitamin K by HPLC with redox-mode electrochemical detection. J Lipid Res. 2005 May;46(5):1053-60. Epub 2005 Feb 1. [PubMed:15722567 ]
Usui Y, Tanimura H, Nishimura N, Kobayashi N, Okanoue T, Ozawa K: Vitamin K concentrations in the plasma and liver of surgical patients. Am J Clin Nutr. 1990 May;51(5):846-52. [PubMed:2333843 ]
Ono M, Ohta H, Ohhira M, Sekiya C, Namiki M: Measurement of immunoreactive prothrombin, des-gamma-carboxy prothrombin, and vitamin K in human liver tissues: overproduction of immunoreactive prothrombin in hepatocellular carcinoma. Am J Gastroenterol. 1990 Sep;85(9):1149-54. [PubMed:1697141 ]
Suzuki S, Iwata G, Sutor AH: Vitamin K deficiency during the perinatal and infantile period. Semin Thromb Hemost. 2001;27(2):93-8. [PubMed:11372776 ]
Wermuth B, Platts KL, Seidel A, Oesch F: Carbonyl reductase provides the enzymatic basis of quinone detoxication in man. Biochem Pharmacol. 1986 Apr 15;35(8):1277-82. [PubMed:3083821 ]
Price RJ, Mistry H, Wield PT, Renwick AB, Beamand JA, Lake BG: Comparison of the toxicity of allyl alcohol, coumarin and menadione in precision-cut rat, guinea-pig, cynomolgus monkey and human liver slices. Arch Toxicol. 1996;71(1-2):107-11. [PubMed:9010592 ]
Thijssen HH, Drittij-Reijnders MJ: Vitamin K status in human tissues: tissue-specific accumulation of phylloquinone and menaquinone-4. Br J Nutr. 1996 Jan;75(1):121-7. [PubMed:8785182 ]
Iioka H, Moriyama IS, Morimoto K, Akada S, Hisanaga H, Ishihara Y, Ichijo M: Pharmacokinetics of vitamin K in mothers and children in the perinatal period: transplacental transport of vitamin K2 (MK-4). Asia Oceania J Obstet Gynaecol. 1991 Mar;17(1):97-100. [PubMed:2064595 ]
Keller AN, Eckle SB, Xu W, Liu L, Hughes VA, Mak JY, Meehan BS, Pediongco T, Birkinshaw RW, Chen Z, Wang H, D'Souza C, Kjer-Nielsen L, Gherardin NA, Godfrey DI, Kostenko L, Corbett AJ, Purcell AW, Fairlie DP, McCluskey J, Rossjohn J: Drugs and drug-like molecules can modulate the function of mucosal-associated invariant T cells. Nat Immunol. 2017 Apr;18(4):402-411. doi: 10.1038/ni.3679. Epub 2017 Feb 6. [PubMed:28166217 ]
Varga JM, Kalchschmid G, Klein GF, Fritsch P: Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody. Mol Immunol. 1991 Jun;28(6):641-54. doi: 10.1016/0161-5890(91)90133-5. [PubMed:1650428 ]
ULBRICH AP: Topical application of menadione, a synthetic vitamin K: preliminary report. J Am Osteopath Assoc. 1961 Jan;60:370-4. [PubMed:13779073 ]
Osman AM, Rotteveel S, den Besten PJ, van Noort PC: In vivo exposure of Dreissena polymorpha mussels to the quinones menadione and lawsone: menadione is more toxic to mussels than lawsone. J Appl Toxicol. 2004 Mar-Apr;24(2):135-41. doi: 10.1002/jat.963. [PubMed:15052609 ]
Thijssen HH, Vervoort LM, Schurgers LJ, Shearer MJ: Menadione is a metabolite of oral vitamin K. Br J Nutr. 2006 Feb;95(2):260-6. doi: 10.1079/bjn20051630. [PubMed:16469140 ]
Chen Q, Cederbaum AI: Menadione cytotoxicity to Hep G2 cells and protection by activation of nuclear factor-kappaB. Mol Pharmacol. 1997 Oct;52(4):648-57. doi: 10.1124/mol.52.4.648. [PubMed:9380028 ]

Showing NP-Card for 2-Methyl-1,4-napthoquinone (NP0331764)

MOL for NP0331764 (2-Methyl-1,4-napthoquinone)

3D MOL for NP0331764 (2-Methyl-1,4-napthoquinone)

3D SDF for NP0331764 (2-Methyl-1,4-napthoquinone)

3D-SDF for NP0331764 (2-Methyl-1,4-napthoquinone)

PDB for NP0331764 (2-Methyl-1,4-napthoquinone)

3D PDB for NP0331764 (2-Methyl-1,4-napthoquinone)

SMILES for NP0331764 (2-Methyl-1,4-napthoquinone)

INCHI for NP0331764 (2-Methyl-1,4-napthoquinone)

Structure for NP0331764 (2-Methyl-1,4-napthoquinone)

3D Structure for NP0331764 (2-Methyl-1,4-napthoquinone)