Menadione
PubChem CID: 4055
Connections displayed (default: 10).
Loading graph...
| Compound Synonyms | menadione, 58-27-5, Vitamin K3, 2-Methyl-1,4-naphthoquinone, 2-methylnaphthalene-1,4-dione, Menaphthone, Kayquinone, 2-Methylnaphthoquinone, Thyloquinone, Kappaxin, Kayklot, Klottone, Kolklot, Panosine, Kanone, 2-Methyl-1,4-naphthalenedione, Menadion, Menaphthon, Kipca, Prokayvit, Aquakay, Aquinone, Hemodal, Kaergona, Mitenon, Mitenone, Karcon, Kareon, Kativ-G, Kaykot, Koaxin, Synkay, K-Thrombyl, K-Vitan, Kappaxan, Juva-K, Vitamin K 3, Menaquinone 0, 2-Methyl-1,4-naphthochinon, Vitamin K2(0), Vitamin K0, Memodol, Usaf ek-5185, 3-Methyl-1,4-naphthoquinone, Menaphtone, 2-Methyl-1,4-naftochinon, 1,4-Naphthalenedione, 2-methyl-, 2-methyl-1,4-dihydronaphthalene-1,4-dione, Menaphthene, Kaynone, 1,4-Naphthoquinone, 2-methyl-, Menadione (Vitamin K3), NSC 4170, MFCD00001681, CCRIS 6672, HSDB 3354, Menaquinone O, Methyl-1,4-naphthoquinone, NSC-4170, EINECS 200-372-6, UNII-723JX6CXY5, 723JX6CXY5, DTXSID4021715, MNQ, 1,4-naphthalenedione, 2-methyl, CHEBI:28869, AI3-14700, NSC4170, Menadione [USP:BAN], CHEMBL590, 2-Methyl-1,4-naphthalendione, MLS000069420, DTXCID801715, Menadionum, Menadione (Vitamin K3) 10 microg/mL in Acetonitrile, 34524-96-4, Kappaxan (VAN), VK3, CAS-58-27-5, Menadione semiquinone, NCGC00016258-02, Menadione (USP:BAN), SMR000059102, MENADIONE (MART.), MENADIONE [MART.], MENADIONE (USP-RS), MENADIONE [USP-RS], MENADIONE (EP MONOGRAPH), MENADIONE [EP MONOGRAPH], MENADIONE (USP MONOGRAPH), MENADIONE [USP MONOGRAPH], 2-Methyl-1,4-naftochinon [Czech], Menadione (USP), Kappaxin (TN), 2-Methyl-1,4-naphthochinon [German], PHYTOMENADIONE IMPURITY A (EP IMPURITY), PHYTOMENADIONE IMPURITY A [EP IMPURITY], SR-01000712386, 2-Methyl-1,4-naphthodione, Methyl-1,4-naphthalenedione, Mendione, 1,4-Dihydro-2-methylnaphthalene-1,4-dione, Menadione Phenolic, 2-methyl-1,4-naphthoquinone, 5, Menadione, 9, Menadione,(S), Phytomenadione Imp. A (EP), Menadione, 2-methylnaphthalene-1,4-dione, Phytomenadione Impurity A, Menadione1528, Prestwick_313, Menadione, 98%, Menadione (Standard), Menadione, crystalline, Spectrum_001228, SpecPlus_000191, MENADIONE [MI], MENADIONE [HSDB], Opera_ID_1802, Prestwick0_000459, Prestwick1_000459, Prestwick2_000459, Prestwick3_000459, Spectrum2_001194, Spectrum4_000722, Spectrum5_001764, MENADIONE [VANDF], M0373, NCIMech_000105, cid_4055, MENADIONE [WHO-DD], 2-methyl-1,4-napthoquinone, SCHEMBL25970, BSPBio_000538, KBioGR_000984, KBioGR_002527, KBioSS_001708, KBioSS_002535, 2-methyl-1,4 naphthoquinone, MLS001148443, BIDD:ER0556, DivK1c_000080, DivK1c_006287, SPECTRUM1502254, SPBio_001267, SPBio_002477, 3-methyl-1,4-naphthalenedione, BPBio1_000592, MENADIONE [ORANGE BOOK], 2-Methyl-[1,4]-naphthoquinone, BDBM24778, HMS500D22, HY-B0332R, KBio1_000080, KBio1_001231, KBio2_001708, KBio2_002527, KBio2_004276, KBio2_005095, KBio2_006844, KBio2_007663, KBio3_003005, WLN: L66 BV EVJ C1, cMAP_000077, NINDS_000080, Bio1_000471, Bio1_000960, Bio1_001449, HMS1569K20, HMS1921P06, HMS2092F12, HMS2096K20, HMS2232A09, HMS2234J16, HMS3371M08, HMS3373A12, HMS3655P03, HMS3869N03, Pharmakon1600-01502254, BCP25699, HY-B0332, STR01143, Tox21_110334, Tox21_301367, BBL027351, CCG-35354, Menadione (K3), analytical standard, NSC758200, s1949, STL377874, AKOS004910447, AKOS025244105, Tox21_110334_1, DB00170, FM11258, FS-2556, NSC-758200, SB17255, IDI1_000080, QTL1_000056, USEPA/OPP Pesticide Code: 006319, NCGC00016258-01, NCGC00016258-03, NCGC00016258-04, NCGC00016258-06, NCGC00016258-07, NCGC00016258-08, NCGC00094978-01, NCGC00094978-02, NCGC00255225-01, 2-Methyl-1,4-naphthoquinone, Vitamin K3, AC-34841, NCI60_003945, SMR000653532, SY018303, SBI-0051776.P002, Menadione, meets USP testing specifications, NS00010106, SW219798-1, C05377, D02335, EN300-125382, Q192471, 1,4-Naphthalenedione, 2-methyl-, radical ion(1-), SR-01000712386-2, SR-01000712386-5, SR-01000712386-6, VITAMIN K3, 2-METHYL-1,4-NAPHTHALENEDIONE, BRD-K78126613-001-16-0, BRD-K78126613-001-27-7, BRD-K78126613-001-28-5, BRD-K78126613-001-29-3, Vitamin K3, 2-Methyl-1,4-naphthoquinone, Menaphthone, Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalene, Z1255430959, Menadione, European Pharmacopoeia (EP) Reference Standard, 03AAE1E9-B215-45AF-976C-91E61894A467, Menadione, United States Pharmacopeia (USP) Reference Standard, Menadione, Pharmaceutical Secondary Standard, Certified Reference Material, InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H, 2-Methyl-1,4-naphthoquinone, Vitamin K2(0), Vitamin K3, 2-Methyl-1,4-dihydronaphthalene-1,4-dione, 200-372-6 |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 34.1 |
| Hydrogen Bond Donor Count | 0.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | CC1CCC(C)C2CCCCC12 |
| Np Classifier Class | Naphthoquinones |
| Deep Smiles | O=CC=CC)C=O)cc6cccc6 |
| Heavy Atom Count | 13.0 |
| Classyfire Class | Naphthalenes |
| Description | Prothrombogenic vitamin (synthetic) A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. -- Pubchem, 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. 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. Moreover, menadione supplements have been banned by the FDA because of their high toxicity., It is sometimes called vitamin K3, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13, It is also known as "menaphthone"., It is sometimes called vitamin K3, although derivatives of naphthoquinone without the side chain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation to yield menaquinones (MK-n, n=1-13, K2 vitamers), and hence, is better classified as a provitamin., K2 vitamers), and hence, is better classified as a provitamin. -- Wikipedia, Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin Kand is also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times., Menadione is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with a 2-methyl substituent. |
| Scaffold Graph Node Level | OC1CCC(O)C2CCCCC12 |
| Classyfire Subclass | Naphthoquinones |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 288.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Enzyme Uniprot Id | Q9BTZ2, P07225, P22891, Q9BQB6, Q8N0U8 |
| Uniprot Id | Q9BTZ2, Q06278, P16083, P47989, P16435, P42898, Q04771, P05181, P04798, P05177, P11509, P15559, P38435, P00740, P04070, P07225, P22891, P02818, P00742, P08709, Q9BQB6, Q9UHB4, Q8N0U8, n.a., P28593, P00469, P09623, P04818, P30307, P00390, O15770, P14902, P10275, P30305, Q64346, P28563, P09936, P15374, P02545, P04406, Q16637, P10636, P33261, P51450, P14618, Q16665, P00352, Q962Y6, Q9F4F7, P97697, P28482, Q03164, P00883, O97447, P15917, P00811, O75604, P15428, P04637, Q13315, P68871, P54132, P08684, P10635, P10253, P11712, O54754, Q9Z0U5, P80456, Q5FB27, Q8WTS1, O60240, Q96KQ7, Q9UIF8, P11473, Q9UNA4, Q9Y253, P84022, O94782, P27338, P21397, P25094, O75496, Q9HC16, Q99700, O42275, P81908, Q3B792, P46426, Q9NUW8, Q13148, Q9Y6L6, Q9NPD5, Q9NR56, O95398, P10845, P9WG47, P30304, Q16762, Q7BGE6, P61604, P0A6F5, P0DTD1, P37840, Q16236, Q03181, P04792, P19838, P05412 |
| Iupac Name | 2-methylnaphthalene-1,4-dione |
| Prediction Hob | 1.0 |
| Class | Naphthalenes |
| Veber Rule | True |
| Classyfire Superclass | Benzenoids |
| Target Id | NPT2927, NPT1557, NPT1078, NPT911, NPT2663, NPT2662, NPT483, NPT1224, NPT93, NPT51, NPT213, NPT52, NPT211, NPT94, NPT282, NPT45, NPT151, NPT539, NPT524, NPT2930, NPT58, NPT109, NPT110, NPT60, NPT212, NPT2742, NPT208, NPT582, NPT261, NPT3060, NPT920 |
| Xlogp | 2.2 |
| Superclass | Benzenoids |
| Subclass | Naphthoquinones |
| Gsk 4 400 Rule | True |
| Molecular Formula | C11H8O2 |
| Scaffold Graph Node Bond Level | O=C1C=CC(=O)c2ccccc21 |
| Prediction Swissadme | 0.0 |
| Inchi Key | MJVAVZPDRWSRRC-UHFFFAOYSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.0909090909090909 |
| Logs | -3.221 |
| Rotatable Bond Count | 0.0 |
| State | Solid |
| Logd | 1.966 |
| Synonyms | 1, 4-Naphthoquinone, 2-methyl-, 1,4-Naphthalenedione, 2-methyl-, 1,4-Naphthalenedione, 2-methyl-, radical ion(1-), 1,4-Naphthoquinone, 2-methyl-, 2-Methyl-1,4-naftochinon, 2-Methyl-1,4-naphthalendione, 2-Methyl-1,4-naphthalenedione, 2-Methyl-1,4-naphthalenedione, 9CI, 2-Methyl-1,4-naphthochinon, 2-Methyl-1,4-naphthochinon (GERMAN), 2-Methyl-1,4-naphthodione, 2-Methyl-1,4-naphthoquinone, 2-methyl-1,4-naphthoquinone, 5, 2-methylnaphthalene-1,4-dione, 2-Methylnaphthoquinone, 3-Methyl-1,4-naphthoquinone, Aquakay, Aquinone, Hemodal, Juva-k, K-thrombyl, K-vitan, Kaergona, Kanone, Kappaxin, Kappaxin (TN), Karcon, Kareon, Kativ-g, Kayklot, Kaykot, Kaynone, Kayquinone, Kipca, Kipca-oil soluble, Kipca, oil soluble, Klottone, Koaxin, Kolklot, Memodol, Menadion, Menadione, Menadione (K3), Menadione (usp), Menadione [usan:ban], Menadione semiquinone, Menadione sodium bisulfite, Menadione, BAN, USAN, Menadionum, Menaphthene, Menaphthon, Menaphthone, Menaphtone, Menaquinone 0, Menaquinone o, Methyl-1,4-naphthalenedione, Methyl-1,4-naphthoquinone, Methylnaphthoquinone, Mitenon, Mitenone, MNQ, Naphthoquinone, methyl-, Panosine, Prokayvit, Synkay, Thyloquinone, Vicasol, Vikasol, Vitamin K 3, Vitamin K0, Vitamin k2, Vitamin K2(0), Vitamin K3, Vitamin K3 : 2-Methyl-1,4-naphthoquinone, Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalene, Juva-K, K-Thrombyl, K-Vitan, Kappaxan, Menaquinone, Menaquinone O, Vitamin K2, Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene, Bisulfite, menadione, Bisulfite, menadione sodium, Menadione sodium bisulfite, trihydrate, Vitamin K3 sodium bisulfite, Menadione bisulfite, Sodium bisulfite, menadione, 2-methyl-1,4-naphthoquinone, menadione, vitamin k3 |
| Substituent Name | Naphthoquinone, Aryl ketone, Quinone, Ketone, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aromatic homopolycyclic compound |
| Esol Class | Soluble |
| Functional Groups | CC1=CC(=O)ccC1=O |
| Compound Name | Menadione |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 172.052 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 172.052 |
| Hydrogen Bond Acceptor Count | 2.0 |
| Molecular Weight | 172.18 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Lipinski Rule Of 5 | True |
| Esol | -2.6350730615384617 |
| Inchi | InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 |
| Smiles | CC1=CC(=O)C2=CC=CC=C2C1=O |
| Nring | 2.0 |
| Np Classifier Biosynthetic Pathway | Polyketides |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Naphthoquinones |
| Np Classifier Superclass | Naphthalenes |
- 1. Outgoing r'ship
FOUND_INto/from Allium Stipitatum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Asplenium Yoshinagae (Plant) Rel Props:Reference:ISBN:9788185042114 - 3. Outgoing r'ship
FOUND_INto/from Juglans Regia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Typha Angustifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all