Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5202)
Drug Name
Phytonadione
Synonyms
Phyllochinon; Phyllohydroquinone; Phytomenadione; Fitomenadione [DCIT]; Phyllochinon [German]; LT00452032; Fitomenadiona [INN-Spanish]; Mephyton (TN); Phylloquinone (8CI); Phytomenadione (INN); Phytomenadionum [INN-Latin]; Phytonadione [USAN:JAN]; Vitamin K1 (TN); Vitamin K1 (VAN); Vitamin K1 (generic); Phythyl-menadion (GERMAN); Phytonadione (JP15/USP); 1,4-Naphthalenedione, 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl)-, radical ion(1-); 2-(3,7,11,15-Tetramethylhexadec-2-enyl)-3-methylnaphthalene-1,4-dione; 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalened-ione; 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione; 2-Methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone; 2-Methyl-3-phythyl-1,4-naphthochinon; 2-Methyl-3-phytyl-1,4-naphthochinon; 2-Methyl-3-phytyl-1,4-naphthochinon [German]; 2-methyl-3-(3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione; 2-methyl-3-[(E)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione; 3-Phytylmenadione
Indication Bleeding disorder [ICD11: GA20-GA21] Approved [1]
Vitamin K deficiency [ICD11: ICD11: 5B55-5B5F] Approved [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 450.7 Topological Polar Surface Area 34.1
Heavy Atom Count 33 Rotatable Bond Count 14
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5284607
ChEBI ID
CHEBI:18067
CAS Number
79083-00-4
TTD Drug ID
D00FSV
Formula
C31H46O2
Canonical SMILES
CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
InChI
InChI=1S/C31H46O2/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/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1
InChIKey
MBWXNTAXLNYFJB-NKFFZRIASA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Hydroxyvitamin K1 DM017132 N. A. Oxidation - Hydroxylation 1 [7] , [4] , [8] , [9] , [10]
Quinone DM006833 N. A. Unclear - Unclear 1 [5]
Vitamin K 5 Carbon Metabolite DM017134 N. A. Unclear - Unclear 1 [7] , [4] , [8] , [9] , [10]
Vitamin K 7 Carbon Metabolite DM017135 N. A. Unclear - Unclear 1 [7] , [4] , [8] , [9] , [10]
Hydroquinone DM005670
785
Unclear - Unclear 2 [5]
Phylloquinone carboxylic acid metabolite DM017133 N. A. Oxidation - Oxidation 2 [3]
Menatetrenone DM015432
5282367
Unclear - Unclear 3 [5]
Vitamin K epoxide DM015094
91577
Unclear - Unclear 4 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008145 Phytonadione Quinone Unclear - Unclear Unclear [5]
MR008149 Phytonadione Hydroxyvitamin K1 Oxidation - Hydroxylation CYP4F2 [7], [4], [8], [9], [10]
MR008151 Phytonadione Vitamin K 5 Carbon Metabolite Unclear - Unclear Unclear [7], [4], [8], [9], [10]
MR008152 Phytonadione Vitamin K 7 Carbon Metabolite Unclear - Unclear Unclear [7], [4], [8], [9], [10]
MR008150 Hydroxyvitamin K1 Phylloquinone carboxylic acid metabolite Oxidation - Oxidation Unclear [3]
MR008146 Quinone Hydroquinone Unclear - Unclear Unclear [5]
MR008147 Hydroquinone Menatetrenone Unclear - Unclear NQO1 ... [5]
MR008148 Menatetrenone Vitamin K epoxide Unclear - Unclear GGCX [11]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 4F2 (CYP4F2) DME0025 Homo sapiens
CP4F2_HUMAN
1.14.13.30
[3]
Cytochrome P450 4F2 (CYP4F2) DME0025 Homo sapiens
CP4F2_HUMAN
1.14.13.30
[4]
Quinone reductase 1 (NQO1) DME0097 Homo sapiens
NQO1_HUMAN
1.6.5.2
[5]
UbiA prenyltransferase domain-containing protein 1 (UBIAD1) DMEN750 Homo sapiens
UBIA1_HUMAN
2.5.1.-
[5]
UbiA prenyltransferase domain-containing protein 1 (UBIAD1) DMEN750 Homo sapiens
UBIA1_HUMAN
2.5.1.-
[4]
Vitamin K-dependent gamma-carboxylase (GGCX) DMEN212 Homo sapiens
VKGC_HUMAN
4.1.1.90
[6]
Vitamin K1 2,3-epoxide reductase 1 (VKOR) DME0149 Homo sapiens
VKOR1_HUMAN
1.17.4.4
[5]
VKORC1-like protein 1 (VKORC1L1) DME0440 Homo sapiens
VKORL_HUMAN
1.17.4.4
[5]
⏷ Show the Full List of 8  DME(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5286).
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5286).
3 DrugBank(Pharmacology-Metabolism):Phytonadione
4 Vitamin K nutrition, metabolism, and requirements: current concepts and future research
5 Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis
6 Structure and function of vitamin K epoxide reductase
7 Metabolism of vitamin K1 (phylloquinone) in man
8 Dietary reference values for vitamin K
9 Preparative isolation and characterization of the urinary aglycones of vitamin K1 (phylloquinone in man
10 Cytochrome P450-dependent catabolism of vitamin K: -hydroxylation catalyzed by human CYP4F2 and CYP4F11
11 VKORC1L1, an enzyme mediating the effect of vitamin K in liver and extrahepatic tissues. Nutrients. 2018 Jul 26;10(8). pii: E970.

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