Deoxylapachol

Details

• Internal ID: 5dfa08ac-299e-4106-9fba-c9807bb577df
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin K compounds
• IUPAC Name: 2-(3-methylbut-2-enyl)naphthalene-1,4-dione
• SMILES (Canonical): CC(=CCC1=CC(=O)C2=CC=CC=C2C1=O)C
• SMILES (Isomeric): CC(=CCC1=CC(=O)C2=CC=CC=C2C1=O)C
• InChI: InChI=1S/C15H14O2/c1-10(2)7-8-11-9-14(16)12-5-3-4-6-13(12)15(11)17/h3-7,9H,8H2,1-2H3
• InChI Key: OSDFYZPKJKRCRR-UHFFFAOYSA-N
• Popularity: 26 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.27 g/mol
• Exact Mass: 226.099379685 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 3568-90-9
• 1,4-Naphthalenedione, 2-(3-methyl-2-butenyl)-
• 2-(3-methylbut-2-enyl)naphthalene-1,4-dione
• 2-Deoxylapachol
• CHEBI:4414
• M5RT9GV702
• CHEBI:28192
• NSC 123507
• NSC-123507
• 1,4-Naphthoquinone, 2-(3-methyl-2-butenyl)-
• prenylnaphthoquinone
• DESOXYLAPACHOL
• 2-demethylmenaquinones
• a 2-demethylmenaquinone
• UNII-M5RT9GV702
• CHEMBL32570
• SCHEMBL2682330
• DTXSID40189186
• BCP32056
• HY-N3733
• NSC123507
• AKOS032948786
• MS-23280
• CS-0024127
• E72228
• 2-(3-Methylbut-2-en-1-yl)naphthalene-1,4-dione
• 2-(3-METHYL-2-BUTENYL)-1,4-NAPHTHOQUINONE
• Q27106375
• 1,4-NAPHTHALENEDIONE, 2-(3-METHYL-2-BUTEN-1-YL)-
• 2-(3-methylbut-2-en-1-yl)-1,4-dihydronaphthalene-1,4-dione
• 2-Deoxylapachol;1,4-Naphthalenedione, 2-(3-methyl-2-butenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8650	86.50%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8147	81.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9462	94.62%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5231	52.31%
P-glycoprotein inhibitior	-	0.8380	83.80%
P-glycoprotein substrate	-	0.9241	92.41%
CYP3A4 substrate	-	0.6042	60.42%
CYP2C9 substrate	-	0.7739	77.39%
CYP2D6 substrate	-	0.8299	82.99%
CYP3A4 inhibition	-	0.7816	78.16%
CYP2C9 inhibition	+	0.9147	91.47%
CYP2C19 inhibition	+	0.8825	88.25%
CYP2D6 inhibition	+	0.6804	68.04%
CYP1A2 inhibition	+	0.9022	90.22%
CYP2C8 inhibition	-	0.9770	97.70%
CYP inhibitory promiscuity	+	0.9245	92.45%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8634	86.34%
Carcinogenicity (trinary)	Non-required	0.6432	64.32%
Eye corrosion	-	0.9860	98.60%
Eye irritation	+	0.9276	92.76%
Skin irritation	-	0.5761	57.61%
Skin corrosion	-	0.8951	89.51%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5547	55.47%
Micronuclear	-	0.7267	72.67%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	+	0.8980	89.80%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6084	60.84%
Acute Oral Toxicity (c)	III	0.5523	55.23%
Estrogen receptor binding	+	0.8542	85.42%
Androgen receptor binding	+	0.6184	61.84%
Thyroid receptor binding	-	0.5313	53.13%
Glucocorticoid receptor binding	+	0.7077	70.77%
Aromatase binding	+	0.7275	72.75%
PPAR gamma	+	0.7109	71.09%
Honey bee toxicity	-	0.8698	86.98%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9942	99.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.51%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.35%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	91.33%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.42%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.29%	82.69%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.38%	96.67%
CHEMBL3401	O75469	Pregnane X receptor	85.82%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	84.06%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.51%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.78%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.10%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.22%	85.14%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.01%	85.94%

Plants that contains it

• Catalpa ovata
• Cichorium intybus
• Handroanthus impetiginosus
• Lactuca serriola
• Tecomella undulata
• Tectona grandis

Cross-Links

• PubChem: 97448
• NPASS: NPC157778
• ChEMBL: CHEMBL32570
• LOTUS: LTS0163831
• wikiData: Q27106375