Structure via PubChem · Public domain (PubChem)
menatetrenone
Sign in to saveAlso known as menaquinone 4, Menaquinone K4, 2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthoquinone, 2-Methyl-3-trans-tetraprenyl-1,4-naphthoquinone, 2-Methyl-3-geranylgeranyl-1,4-naphthoquinone, Vitamin MK 4, MK4, MK-4
Menatetrenone (INN), also known as menaquinone-4 (MK-4), is one of the nine forms of vitamin K2.
Chemical data
- Formula
- C31H40O2
- Molecular weight
- 444.6 g/mol
- IUPAC name
- 2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione
- SMILES
- CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
- InChIKey
- DKHGMERMDICWDU-GHDNBGIDSA-N
- XLogP
- 8.9
- Polar surface area
- 34.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- hepatocellular carcinoma, postmenopausal osteoporosis, osteoporosis, bone disease
via ChEMBL · EBI
Research
378 papers- Exploring Menatetrenone: Origin, Chemistry, Therapies and Delivery.Journal of the American Nutrition Association · 2025
- Menatetrenone for the treatment of osteoporosis.Expert opinion on pharmacotherapy · 2013
- The efficacy and safety of menatetrenone in the management of osteoporosis: a systematic review and meta-analysis of randomized controlled trials.Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA · 2019
- Menatetrenone (vitamin K2) and bone quality in the treatment of postmenopausal osteoporosis.Nutrition reviews · 2006
- Vitamin K.2006
via PubMed
Wikidata facts
- Subclass of
- menaquinone
- Mass
- 444.303
Show 6 more facts
- subject has role
- primary metabolite
- canonical SMILES
- CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C
- Commons category
- Menatetrenone
- chemical formula
- C₃₁H₄₀O₂
- isomeric SMILES
- CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
- World Health Organisation international non-proprietary name
- menatetrenone
Sources (6)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Biology
- As a medication
- Bioavailbility and dose
- References
Menatetrenone (INN), also known as menaquinone-4 (MK-4), is one of the nine forms of vitamin K2.
== Biology == MK-4 is the major form of Vitamin K in vertebrate animals, including humans and common forms of meat animals. It is produced via conversion of vitamin K1 in the body, specifically in the testes, pancreas and arterial walls. The conversion is not dependent on gut bacteria, occurring in germ-free rats and in parenterally-administered K1 in rats. Tissues that accumulate high amounts of MK-4 have a capacity to convert up to 90% of the available K1 into MK-4.
Excerpted from Wikipedia’s “menatetrenone” article, available under the CC BY-SA 4.0 licence.