Phylloquinol (BioDeep_00000005172)

 

Secondary id: BioDeep_00000019517, BioDeep_00000639420

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


[R-[R*,r*-(e)]]-2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenediol

化学式: C31H48O2 (452.3654)
中文名称: 二氢维生素K1
谱图信息: 最多检出来源 Homo sapiens(plant) 6.59%

分子结构信息

SMILES: CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1C
InChI: InChI=1S/C31H48O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24,32-33H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1

描述信息

Phylloquinol, also known as vitamin k1 hydroquinone or phytonadiol, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Thus, phylloquinol is considered to be a quinone lipid molecule. Phylloquinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Phylloquinol can be found in a number of food items such as olive, sweet basil, mung bean, and yellow bell pepper, which makes phylloquinol a potential biomarker for the consumption of these food products.
Phylloquinol, also known as vitamin K1 hydroquinone or reduced vitamin K1, is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K is a family of phylloquinones that contain a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Several forms of vitamin K have been identified: vitamin K1 derived from plants, vitamin K2 (menaquinone) from bacteria and synthetic naphthoquinone provitamins, and vitamin K3 (menadione).

同义名列表

21 个代谢物同义名

[R-[R*,r*-(e)]]-2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenediol; [R-[R*,R*-(E)]]-2-methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)naphthalene-1,4-diol; 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-diol; 2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-1,4-naphthalenediol; 2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenediol; (e)-2-Methyl-3-phytyl-1,4-naphthalenediol; 2-Methyl-3-phytyl-1,4-naphthohydroquinone; alpha-Phyllohydroquinone; vitamin K1 hydroquinone; Vitamin K hydroquinone; Reduced phylloquinone; Dihydro-phylloquinone; Α-phyllohydroquinone; Dihydroxyvitamin K; Phyllohydroquinone; Reduced vitamin K1; Dihydrovitamin K1; Reduced vitamin K; Phylloquinol; Phytonadiol; Phylloquinol



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

258 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(4)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(251)

COVID-19 Disease Map(0)

PathBank(2)

  • Vitamin K Metabolism: Carbon dioxide + Oxygen + Peptidyl-4-carboxyglutamate + Phylloquinol ⟶ Peptidyl-glutamate + Vitamin K1 2,3-epoxide + Water
  • Phylloquinol Biosynthesis: 2-carboxy-1,4-naphthoquinone + Hydrogen Ion + Phytyl diphosphate ⟶ Carbon dioxide + Demethylphylloquinone + Pyrophosphate

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 6 BGLAP, GAS6, GLA, GRP, NQO1, TXN
Peripheral membrane protein 2 CYP1B1, HSD17B6
Endoplasmic reticulum membrane 8 CYP1B1, EBP, GLA, PROS1, SERP1, TYRO3, VKORC1, VKORC1L1
Nucleus 3 NQO1, TXN, TYRO3
cytosol 3 NQO1, SERP1, TXN
dendrite 2 BGLAP, NQO1
nucleoplasm 1 TXN
Cell membrane 2 AXL, TYRO3
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 4 EBP, TPRA1, VKORC1, VKORC1L1
Synapse 1 NQO1
cell surface 2 AXL, TYRO3
Golgi apparatus 2 GLA, SERPINA1
Golgi membrane 1 PROS1
neuronal cell body 1 NQO1
Cytoplasm, cytosol 1 NQO1
Lysosome 1 GLA
plasma membrane 6 AXL, F7, F9, PROS1, TPRA1, TYRO3
Membrane 7 AXL, CYP1B1, GLA, NQO1, SERP1, TPRA1, TYRO3
extracellular exosome 8 AXL, F9, GAS6, GLA, MGP, PROS1, SERPINA1, TXN
Lumenal side 1 HSD17B6
endoplasmic reticulum 7 EBP, HSD17B6, PROS1, SERP1, SERPINA1, VKORC1, VKORC1L1
extracellular space 8 AXL, BGLAP, F7, F9, GAS6, GRP, PROS1, SERPINA1
lysosomal lumen 1 GLA
mitochondrion 1 CYP1B1
intracellular membrane-bounded organelle 4 AXL, CYP1B1, HSD17B6, SERPINA1
Microsome membrane 2 CYP1B1, HSD17B6
Single-pass type I membrane protein 2 AXL, TYRO3
Secreted 7 BGLAP, F7, F9, GAS6, GRP, PROS1, TXN
extracellular region 9 BGLAP, F7, F9, GAS6, GLA, GRP, PROS1, SERPINA1, TXN
Single-pass membrane protein 1 SERP1
nuclear membrane 1 EBP
Secreted, extracellular space, extracellular matrix 1 GRP
actin cytoskeleton 1 AXL
perikaryon 1 BGLAP
cytoplasmic vesicle 1 EBP
COPII-coated ER to Golgi transport vesicle 1 SERPINA1
vesicle 2 BGLAP, F7
extracellular matrix 2 GRP, MGP
collagen-containing extracellular matrix 4 F7, F9, MGP, SERPINA1
receptor complex 2 AXL, TYRO3
Cell projection, neuron projection 1 GRP
neuron projection 1 GRP
blood microparticle 1 PROS1
nuclear envelope 2 EBP, TYRO3
Nucleus envelope 1 EBP
ficolin-1-rich granule lumen 1 SERPINA1
secretory granule lumen 1 GRP
Golgi lumen 5 BGLAP, F7, F9, GAS6, PROS1
endoplasmic reticulum lumen 5 BGLAP, F7, F9, GAS6, SERPINA1
platelet alpha granule lumen 3 GAS6, PROS1, SERPINA1
azurophil granule lumen 1 GLA
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GLA, SERPINA1
neuronal dense core vesicle 1 GRP
endoplasmic reticulum-Golgi intermediate compartment 1 GLA
cytoplasmic microtubule 1 SERP1
ribosome 1 SERP1
Cytoplasmic vesicle, secretory vesicle lumen 1 GRP
serine-type peptidase complex 1 F7


文献列表

  • Anton S M Dofferhoff, Ianthe Piscaer, Leon J Schurgers, Margot P J Visser, Jody M W van den Ouweland, Pim A de Jong, Reinoud Gosens, Tilman M Hackeng, Henny van Daal, Petra Lux, Cecile Maassen, Esther G A Karssemeijer, Cees Vermeer, Emiel F M Wouters, Loes E M Kistemaker, Jona Walk, Rob Janssen. Reduced Vitamin K Status as a Potentially Modifiable Risk Factor of Severe Coronavirus Disease 2019. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America. 2021 12; 73(11):e4039-e4046. doi: 10.1093/cid/ciaa1258. [PMID: 32852539]
  • Dion Groothof, Adrian Post, Reinold O B Gans, Stephan J L Bakker. Reduced Vitamin K Status and Coronavirus Disease 2019: An Epiphenomenon of Impaired Kidney Function?. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America. 2021 10; 73(7):1324-1325. doi: 10.1093/cid/ciab164. [PMID: 33630997]
  • Toshiro Sato, Rumi Ozaki, Shuichi Kamo, Yusuke Hara, Satoru Konishi, Yosuke Isobe, Sanshiroh Saitoh, Hiroshi Harada. The biological activity and tissue distribution of 2',3'-dihydrophylloquinone in rats. Biochimica et biophysica acta. 2003 Aug; 1622(3):145-50. doi: 10.1016/s0304-4165(03)00135-1. [PMID: 12928110]
  • A Bridge, R Barr, D J Morré. The plasma membrane NADH oxidase of soybean has vitamin K(1) hydroquinone oxidase activity. Biochimica et biophysica acta. 2000 Feb; 1463(2):448-58. doi: 10.1016/s0005-2736(99)00239-4. [PMID: 10675521]
  • S L Booth, K W Davidson, A H Lichtenstein, J A Sadowski. Plasma concentrations of dihydro-vitamin K1 following dietary intake of a hydrogenated vitamin K1-rich vegetable oil. Lipids. 1996 Jul; 31(7):709-13. doi: 10.1007/bf02522886. [PMID: 8827693]
  • S L Booth, J A Pennington, J A Sadowski. Dihydro-vitamin K1: primary food sources and estimated dietary intakes in the American diet. Lipids. 1996 Jul; 31(7):715-20. doi: 10.1007/bf02522887. [PMID: 8827694]
  • Y Haroon, D S Bacon, J A Sadowski. Liquid-chromatographic determination of vitamin K1 in plasma, with fluorometric detection. Clinical chemistry. 1986 Oct; 32(10):1925-9. doi: 10.1093/clinchem/32.10.1925. [PMID: 3757212]