Np mrd loader

Record Information
Version1.0
Created at2023-06-09 20:02:21 UTC
Updated at2024-05-13 01:10:25 UTC
NP-MRD IDNP0331682
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Methyl-1,4-Naphthoquinone
DescriptionMenadione, 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: 28166217) (PMID: 1650428) (PMID: 15052609) (PMID: 16469140).
Structure
Thumb
Synonyms
ValueSource
2-Methyl-1,4-naphthalenedioneChEBI
2-Methyl-1,4-naphthochinonChEBI
2-Methyl-1,4-naphthoquinoneChEBI
Vitamin K3ChEBI
KappaxinKegg
2-Methyl-1,4-naftochinonHMDB
2-Methyl-1,4-naphthalendioneHMDB
2-Methyl-1,4-naphthodioneHMDB
2-MethylnaphthoquinoneHMDB
3-Methyl-1,4-naphthoquinoneHMDB
AquakayHMDB
AquinoneHMDB
HemodalHMDB
Juva-KHMDB
K-ThrombylHMDB
K-VitanHMDB
KaergonaHMDB
KanoneHMDB
KappaxanHMDB
KarconHMDB
KareonHMDB
Kativ-gHMDB
KayklotHMDB
KaykotHMDB
KaynoneHMDB
KayquinoneHMDB
KipcaHMDB
Kipca-oil solubleHMDB
KlottoneHMDB
KoaxinHMDB
KolklotHMDB
MenadionHMDB
MenaphtheneHMDB
MenaphthonHMDB
MenaphthoneHMDB
MenaphtoneHMDB
MenaquinoneHMDB
Menaquinone OHMDB
MitenonHMDB
MitenoneHMDB
MNQHMDB
PanosineHMDB
ProkayvitHMDB
SynkayHMDB
ThyloquinoneHMDB
Vitamin K0HMDB
Vitamin K2HMDB
Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthaleneHMDB
Bisulfite, menadioneHMDB
VicasolHMDB
Bisulfite, menadione sodiumHMDB
Menadione sodium bisulfiteHMDB
VikasolHMDB
Vitamin K 3HMDB
Menadione sodium bisulfite, trihydrateHMDB
Vitamin K3 sodium bisulfiteHMDB
Menadione bisulfiteHMDB
Sodium bisulfite, menadioneHMDB
Chemical FormulaC11H8O2
Average Mass172.1800 Da
Monoisotopic Mass172.05243 Da
IUPAC Name2-methyl-1,4-dihydronaphthalene-1,4-dione
Traditional Namemenadione
CAS Registry NumberNot 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 KeyMJVAVZPDRWSRRC-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-05-11View Spectrum
Species
Species of OriginNot 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).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aryl ketone
  • Quinone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.91ALOGPS
logP1.89ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.94ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.54 m³·mol⁻¹ChemAxon
Polarizability17.64 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001892
DrugBank IDDB00170
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000953
KNApSAcK IDNot Available
Chemspider ID3915
KEGG Compound IDC05377
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMenadione
METLIN ID3910
PubChem Compound4055
PDB IDNot Available
ChEBI ID28869
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. ULBRICH AP: Topical application of menadione, a synthetic vitamin K: preliminary report. J Am Osteopath Assoc. 1961 Jan;60:370-4. [PubMed:13779073 ]
  4. 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 ]
  5. 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 ]