Phytonadione

Details

• Internal ID: 41561663-db92-4dfa-837d-5474cfaa264c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin K compounds
• IUPAC Name: 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
• SMILES (Canonical): CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C
• SMILES (Isomeric): 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
• InChI Key: MBWXNTAXLNYFJB-NKFFZRIASA-N
• Popularity: 3,574 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₆O₂
• Molecular Weight: 450.70 g/mol
• Exact Mass: 450.349780706 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 10.90
• Atomic LogP (AlogP): 9.16
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 14

Synonyms

• phytonadione
• 84-80-0
• Phylloquinone
• Phytomenadione
• Phytylmenadione
• 3-Phytylmenadione
• Phyllochinon
• Mephyton
• Monodion
• Synthex P
• Fitomenadiona
• Kinadion
• Kephton
• 2-Methyl-3-phytyl-1,4-naphthoquinone
• Mono-Kay
• Combinal K1
• Kativ N
• alpha-Phylloquinone
• K-Ject
• Phyllochinonum
• Phytomenadionum
• Phytonadionum
• trans-Phylloquinone
• Aqua mephyton
• Antihemorrhagic vitamin
• Fitomenadione
• Vitamin K 1
• Vitamin K1(20)
• Orakay
• 2',3'-trans-Vitamin K1
• 2-Methyl-3-phytyl-1,4-naphthochinon
• Kanavit
• Neokay
• DTXSID8023472
• CHEBI:18067
• Konakion mm
• Konakion mm paed
• S5Z3U87QHF
• NSC-270681
• 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
• 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione
• 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione
• DTXCID003472
• 2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone
• NSC270681
• vitaminum k1
• 2-Methyl-3-((2E)-3,7,11,15-tetramethyl-2-hexadecenyl)naphthoquinone
• Phylloquinone e-
• 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione
• 2-methyl-3-((E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl)naphthalene-1,4-dione
• Vitamin K1 Injectable
• RefChem:6141
• VEDA-K1
• VETA-K1
• VITAMIN K1 PHYTONADIONE
• VITAMIN K1-PHYTONADIONE
• PHYTONADIONE PHYTONADIONE
• VITAMIN K1, PHYTONADIONE
• B02BA01
• A034SE7857
• 2-Methyl-3-((2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl)-1,4-naphthoquinone
• Aquamephyton
• Konakion
• 79083-00-4
• Aqua-Mephytin
• 11104-38-4
• MFCD00214063
• Phylloquinone e-form
• 1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-
• NSC 270681
• VitaminK1
• 1,4-Naphthoquinone, 2-methyl-3-phytyl-
• 2-Methyl-3-((7R,11R,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione
• Phythyl-menadion
• MLF3D1712D
• Phytonadione, (E)-(+/-)-
• C31H46O2
• 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-, (R-(R*,R*-(E)))-
• 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-
• 2-Methyl-3-phythyl-1,4-naphthochinon
• CAS-84-80-0
• rel-2-Methyl-3-((7R,11R,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl)naphthalene-1,4-dione
• Phytonadione, K1
• 1,4-Naphthalenedione, 2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-, [R-[R*,R*-(E)]]-
• 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
• Phyllochinon [German]
• Fitomenadione [DCIT]
• Vitamin K1 (VAN)
• Phytonadione [USP:JAN]
• UNII-S5Z3U87QHF
• Phytomenadione; Phytonadione; Vitamin K1; Phylloquinone
• Fitomenadiona [INN-Spanish]
• Phytomenadionum [INN-Latin]
• a-Phylloquinone
• HSDB 3162
• (E)-phytonadione
• Vitamin K?
• NCGC00159423-02
• EINECS 201-564-2
• EINECS 234-330-3
• EINECS 279-052-3
• Vitamin K1 (contains up to 20% cis isomer)
• vitamin K1, 11
• Vitamin K1 (generic)
• Vitamin K1 (Standard)
• Phytomenadion/Vitamin K1
• PHYTONADIONE [JAN]
• 2-Methyl-3-phytyl-1,4-naphthochinon [German]
• phylloquinone;2-METHYL-3-PHYTYL-1,4-NAPHTHOQUINONE
• Phylloquinone;Phytomenadione
• SCHEMBL3882
• Vitamin K1 (Phylloquinone)
• Vitamin K1, viscous liquid
• CHEMBL1550
• UNII-MLF3D1712D
• PHYTONADIONE, (E)-
• PHYLLOQUINONE, (E)-
• MLS001074732
• BIDD:GT0793
• PHYTOMENADIONE, (E)-
• orb1309849
• 2-Methyl-3-[(2E)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone #
• BDBM24782
• HY-N0684R
• MSK1513
• [r-[r*,R*-(E)]]-2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-napthalenedione
• [r-[r*,R*-(E)]]-2-Methyl-3-(3-7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione
• PHYLLOQUINONE E-FORM [MI]
• GLXC-21157
• HMS2094G09
• HMS2270J10
• Pharmakon1600-01505485
• 10485-69-5
• HY-N0684
• Tox21_111655
• BDBM50553259
• LMPR02030028
• NSC760373
• s4698
• 2-Methyl-3-phytyl-1,4-napthoquinone
• AKOS015841892
• Tox21_111655_1
• CCG-213568
• CS-6376
• DB01022
• FV28716
• NSC-760373
• (R*,R*-(E))-(1)-2-Methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone
• NCGC00159423-03
• Phylloquinone (K1), analytical standard
• AC-34846
• AS-13734
• SMR000112043
• SBI-0206926.P001
• trans-Phytomenadione 100 microg/mL in Ethanol
• AB00698065_04
• 214V063
• EN300-22411510
• F814464
• Q186093
• SR-05000001941
• C31H46O2 (2-methyl-3-phytyl-1,4-naphthoquinone)
• SR-05000001941-1
• BRD-K76661572-001-07-6
• BRD-K76661572-001-08-4
• Z2568644345
• 84C51B31-3CE2-476B-BE66-A84BDD46A513
• VITAMIN K1; 2-METHYL-3-PHYTYL-1,4-NAPHTHOQUINONE
• Phytomenadione, European Pharmacopoeia (EP) Reference Standard
• Phytonadione, United States Pharmacopeia (USP) Reference Standard
• 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalened- ione
• Vitamin K1, BioXtra, >=99.0% (sum of isomers, HPLC), mixtur of isomers
• 1,4-Naphthalenedione, 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl)-
• 1,4-Naphthalenedione, 2-methyl-3-((2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl)-
• Phytonadione, Pharmaceutical Secondary Standard; Certified Reference Material
• 1,4-NAPHTHALENEDIONE, 2-METHYL-3-((2E,7R,11R)-3,7,11,15-TETRAMETHYL-2-HEXADECEN-1-YL)-, REL-
• 2-METHYL-3-((2E,7R,11R)-3,7,11,15-TETRAMETHYL-2-HEXADECENYL)-1,4-NAPHTHALENEDIONE
• 2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenedione;Konakion;Mephyton

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7617	76.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9280	92.80%
OATP1B3 inhibitior	+	0.9142	91.42%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9757	97.57%
P-glycoprotein inhibitior	+	0.7584	75.84%
P-glycoprotein substrate	-	0.7250	72.50%
CYP3A4 substrate	+	0.5230	52.30%
CYP2C9 substrate	-	0.7707	77.07%
CYP2D6 substrate	-	0.8031	80.31%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8958	89.58%
CYP inhibitory promiscuity	+	0.7542	75.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6185	61.85%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6813	68.13%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	-	0.7137	71.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8917	89.17%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	+	0.6964	69.64%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7459	74.59%
Acute Oral Toxicity (c)	IV	0.6192	61.92%
Estrogen receptor binding	+	0.5732	57.32%
Androgen receptor binding	-	0.6936	69.36%
Thyroid receptor binding	-	0.5266	52.66%
Glucocorticoid receptor binding	-	0.4913	49.13%
Aromatase binding	-	0.5518	55.18%
PPAR gamma	+	0.6055	60.55%
Honey bee toxicity	-	0.9320	93.20%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.84%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.75%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.75%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	95.54%	94.73%
CHEMBL2039	P27338	Monoamine oxidase B	92.66%	92.51%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.19%	85.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.17%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.97%	93.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.94%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.58%	82.69%
CHEMBL1907	P15144	Aminopeptidase N	85.16%	93.31%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.64%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.48%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.99%	96.09%
CHEMBL3524	P56524	Histone deacetylase 4	81.40%	92.97%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.79%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.46%	99.17%

Plants that contains it

• Alhagi maurorum
• Arabidopsis thaliana
• Betonica officinalis
• Calendula officinalis
• Cannabis sativa
• Changium smyrnioides
• Coffea arabica
• Prunus domestica
• Secale cereale
• Spinacia oleracea
• Vigna radiata

Cross-Links

• PubChem: 5284607
• NPASS: NPC188844
• LOTUS: LTS0132253
• wikiData: Q186093