PQN

PHYLLOQUINONE

Created: 1999-07-08
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count79
Chiral Atom Count2
Bond Count80
Aromatic Bond Count6
2D diagram of PQN

Chemical Component Summary

NamePHYLLOQUINONE
SynonymsVITAMIN K1; 2-METHYL-3-PHYTYL-1,4-NAPHTHOQUINONE
Systematic Name (OpenEye OEToolkits)2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
FormulaC31 H46 O2
Molecular Weight450.696
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C2c1c(cccc1)C(=O)C(=C2C)C\C=C(/C)CCCC(C)CCCC(C)CCCC(C)C
SMILESCACTVS3.341CC(C)CCC[CH](C)CCC[CH](C)CCCC(C)=CCC1=C(C)C(=O)c2ccccc2C1=O
SMILESOpenEye OEToolkits1.5.0CC1=C(C(=O)c2ccccc2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C
Canonical SMILESCACTVS3.341 CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(/C)=C/CC1=C(C)C(=O)c2ccccc2C1=O
Canonical SMILESOpenEye OEToolkits1.5.0 CC1=C(C(=O)c2ccccc2C1=O)C\C=C(/C)\CCC[C@H](C)CCC[C@H](C)CCCC(C)C
InChIInChI1.03 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
InChIKeyInChI1.03 MBWXNTAXLNYFJB-NKFFZRIASA-N

Drug Info: DrugBank

DrugBank IDDB01022 
NamePhylloquinone
Groups
  • approved
  • investigational
DescriptionVitamin K1, also called phylloquinone or phytonadione, is a fat soluble vitamin.[L33319,L33345] Phylloquinone is a cofactor of the enzyme γ-carboxylase, which modifies and activates precursors to coagulation factors II, VII, IX, and X.[A234264,A234195,A234259] It is indicated in the treatment of coagulation disorders due to faulty formation of coagulation factors II, VII, IX, and X caused by deficiency or interference in the activity of vitamin K.[L33319] Phylloquinone has been synthesized since at least 1939,[A234384] and was approved by the FDA prior to 1955.[L33389]
Synonyms
  • 3-Phytylmenadione
  • 2-Methyl-3-phytyl-1,4-naphthoquinone
  • Phytonadione
  • 2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone
  • Phytonadionum
Brand Names
  • Mvc 9+4 Inj
  • Vitamin K1
  • Pro Pcos Citrus
  • Vitamin D2 and K1
  • Vitamin K1 Inj 10mg/ml USP
IndicationOral phylloquinone is indicated to treat prothrombin deficiency caused by coumarin or indanedione derivatives; and hypoprothrombinemia secondary to antibacterial therapy, salicylates, or obstructive jaundice or biliary fistulas with concomitant bile salt administration.[L33345] Parenteral (intravenous, intramuscular, and subcutaneous) phylloquinone is indicated to treat coagulation disorders due to faulty formation of coagulation factors II, VII, IX, and X caused by vitamin K deficiency or some interference with vitamin K activity.[L33319] These indications include the above indications as well as hypoprothrombinemia secondary to sprue, ulcerative colitis, celiac disease, intestinal resection, pancreatic cystic fibrosis, or regional enteritis; or hypoprothrombinemia caused by interference with vitamin k metabolism.[L33319]
Categories
  • Blood and Blood Forming Organs
  • Coagulants
  • Diet, Food, and Nutrition
  • Diterpenes
  • Drugs that are Mainly Renally Excreted
ATC-CodeB02BA01
CAS number84-80-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Vitamin K-dependent gamma-carboxylaseMAVSAGSARTSPSSDKVQKDKAELISGPRQDSRIGKLLGFEWTDLSSWRR...unknownsubstrate,inducer,cofactor
OsteocalcinMRALTLLALLALAALCIAGQAGAKPSGAESSKGAAFVSKQEGSEVVKRPR...unknownagonist
Leukotriene-B(4) omega-hydroxylase 1MSQLSLSWLGLWPVAASPWLLLLLVGASWLLAHVLAWTYAFYDNCRRLRC...unknownsubstrate
UbiA prenyltransferase domain-containing protein 1MAASQVLGEKINILSGETVKAGDRDPLGNDCPEQDRLPQRSWRQKCASYV...unknownsubstrate
Vitamin K epoxide reductase complex subunit 1MGSTWGSPGWVRLALCLTGLVLSLYALHVKAARARDRDYRALCDVGTAIS...unknownsubstrate,product of
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5284607
ChEMBL CHEMBL1550
ChEBI CHEBI:18067