Phylloquinone (BioCAD00000016294)

plant natural products

Metabolite Card

Formula: C31H46O2 (450.3498)
SMILES: C12C=CC=CC=1C(C(=C(C)C2=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=O

Synonyms [en]

Phylloquinone; phytonadione; Vitamin K1; 2-Methyl-3-phytyl-1,4-naphthoquinone; Phytomenadione; 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Phylloquinone. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000016294). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

phylloquinone

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 11104-38-4
  • CAS Registry Number: 12001-79-5
  • CAS Registry Number: 27696-10-2
  • CAS Registry Number: 3055-96-7
  • CAS Registry Number: 79083-00-4
  • CAS Registry Number: 81818-54-4
  • CAS Registry Number: 84-80-0
  • PubChem: 5280483
  • PubChem: 5284607
  • ChEBI: ChEBI:18067
  • ChEBI: ChEBI:94399
  • HMDB: HMDB0003555
  • HMDB: HMDB0004198
  • LipidMaps: LMPR02030028
  • KEGG: C02059
  • BioCyc: 2-METHYL-3-PHYTYL-14-NAPHTHOQUINONE
  • NCBI MeSH: Vitamin K
  • NCBI MeSH: Vitamin K 1
  • Wikipedia: Phytomenadione
  • DrugBank: DB01022
  • RefMet: RM0135433
  • MoNA: BAF_UVA_POS000861
  • MoNA: BAF_UVA_POS001452
  • MoNA: BAF_UVA_POS001453
  • MoNA: BML81942
  • MoNA: CA000175
  • MoNA: CA000176
  • MoNA: HMDB0015157_c_ms_2301
  • MoNA: HMDB0015157_c_ms_2304
  • MoNA: HMDB0015157_c_ms_2313
  • MoNA: HMDB0015157_c_ms_2318
  • MoNA: HMDB0015157_c_ms_2321
  • MoNA: HMDB0015157_c_ms_2329
  • MoNA: HMDB0015157_c_ms_2332
  • Metlin: METLIN_228
  • Coconut NaturalProduct: CNP0273613.1
  • Coconut NaturalProduct: CNP0331230.1
  • Coconut NaturalProduct: CNP0406627.1
  • Coconut NaturalProduct: CNP0505711.0
  • Coconut NaturalProduct: CNP0600393.1
  • Coconut NaturalProduct: CNP0600393.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03510 1.14.99.20 phylloquinone,hydrogen-donor:oxygen oxidoreductase (2,3-epoxidizing)
KEGG:R03511 1.17.4.4 phylloquinone:oxidized-dithiothreitol oxidoreductase
KEGG:R03816 1.6.5.2 NADH:phylloquinone oxidoreductase
KEGG:R10728 1.14.14.78 phylloquinone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (omega-hydroxyphylloquinone forming)
Rhea:RHEA:13818 1.17.4.4 phylloquinone + [protein]-disulfide + H2O => 2,3-epoxyphylloquinone + [protein]-dithiol
Rhea:RHEA:13819 1.17.4.4 2,3-epoxyphylloquinone + [protein]-dithiol => phylloquinone + [protein]-disulfide + H2O
Rhea:RHEA:13820 1.17.4.4 phylloquinone + [protein]-disulfide + H2O <=> 2,3-epoxyphylloquinone + [protein]-dithiol
Rhea:RHEA:16746 1.14.99.20 phylloquinone + AH2 + O2 => 2,3-epoxyphylloquinone + A + H2O
Rhea:RHEA:16747 1.14.99.20 2,3-epoxyphylloquinone + A + H2O => phylloquinone + AH2 + O2
Rhea:RHEA:16748 1.14.99.20 phylloquinone + AH2 + O2 <=> 2,3-epoxyphylloquinone + A + H2O
Rhea:RHEA:41517 1.14.14.78 phylloquinone + reduced [NADPH—hemoprotein reductase] + O2 => ω-hydroxyphylloquinone + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:41518 1.14.14.78 ω-hydroxyphylloquinone + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => phylloquinone + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:41519 1.14.14.78 phylloquinone + reduced [NADPH—hemoprotein reductase] + O2 <=> ω-hydroxyphylloquinone + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:57745 1.17.4.4 phylloquinol + [protein]-disulfide => phylloquinone + [protein]-dithiol
Rhea:RHEA:57746 1.17.4.4 phylloquinone + [protein]-dithiol => phylloquinol + [protein]-disulfide
Rhea:RHEA:57747 1.17.4.4 phylloquinol + [protein]-disulfide <=> phylloquinone + [protein]-dithiol
Rhea:RHEA:71512 phylloquinone(out) => phylloquinone(in)
Rhea:RHEA:71513 phylloquinone(in) => phylloquinone(out)
Rhea:RHEA:71514 phylloquinone(out) <=> phylloquinone(in)
Rhea:RHEA:74076 phylloquinone + NADH + H+ => phylloquinol + NAD+
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Organism Source

Taxonomy Source

  1. Actinidia deliciosa [ncbi taxid: 3627]
  2. Apium graveolens [ncbi taxid: 4045]
  3. Arabidopsis thaliana [ncbi taxid: 3702]
  4. Brassica oleracea var. sabauda [ncbi taxid: 1216010]
  5. Calendula officinalis [ncbi taxid: 41496]
  6. Cannabis sativa [ncbi taxid: 3483]
  7. Castanea sativa [ncbi taxid: 21020]
  8. Changium smyrnioides [ncbi taxid: 386280]
  9. Cucumis sativus [ncbi taxid: 3659]
  10. Daucus carota [ncbi taxid: 4039]
  11. Hippophae rhamnoides [ncbi taxid: 193516]
  12. Homo sapiens [ncbi taxid: 9606]
  13. Medicago sativa [ncbi taxid: 3879]
  14. Adiantum capillus-veneris [ncbi taxid: 13818]

Pathway Synthetic

pathway id name
Plant Reactome:R-OSA-1119498 vitamin K1
Plant Reactome:R-OSA-2744345 Metabolism and regulation
Plant Reactome:R-OSA-2867929 Cofactor biosyntheses
PlantCyc:SORGHUMBICOLOR_PROUT-PWY L-proline degradation I
PlantCyc:SORGHUMBICOLOR_PWY-7211 superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis
PlantCyc:SPENNELLII_PWY-4261 glycerol degradation I
PlantCyc:SPENNELLII_PROUT-PWY L-proline degradation I
PlantCyc:SPENNELLII_PWY-7211 superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis
PlantCyc:SPENNELLII_PWY0-162 superpathway of pyrimidine ribonucleotides de novo biosynthesis
PlantCyc:SPENNELLII_PWY-6475 trans-lycopene biosynthesis II (oxygenic phototrophs and green sulfur bacteria)
PlantCyc:SPIRODELA_PROUT-PWY L-proline degradation I
PlantCyc:ACOERULEA_PWY-6922 L-Nδ-acetylornithine biosynthesis
PlantCyc:ACOERULEA_PROUT-PWY L-proline degradation I
PlantCyc:ACOERULEA_PWY-6118 glycerol-3-phosphate shuttle
PlantCyc:SUNFLOWER_PROUT-PWY L-proline degradation I
PlantCyc:ACOERULEA_PWY-5690 TCA cycle II (plants and fungi)
PlantCyc:SUNFLOWER_PWY-4261 glycerol degradation I
PlantCyc:SVIRIDIS_PWY-5690 TCA cycle II (plants and fungi)
PlantCyc:SVIRIDIS_PWY0-162 superpathway of pyrimidine ribonucleotides de novo biosynthesis
PlantCyc:AHALLERI_PWY-6475 trans-lycopene biosynthesis II (oxygenic phototrophs and green sulfur bacteria)
View All Pathways