8-Hydroxy-6-(1-hydroxy-4-methylpent-3-enyl)-5-methoxynaphthalene-1,4-dione

Details

• Internal ID: 279f6ea3-9942-4259-aa4f-09d788b40f46
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 8-hydroxy-6-(1-hydroxy-4-methylpent-3-enyl)-5-methoxynaphthalene-1,4-dione
• SMILES (Canonical): CC(=CCC(C1=CC(=C2C(=O)C=CC(=O)C2=C1OC)O)O)C
• SMILES (Isomeric): CC(=CCC(C1=CC(=C2C(=O)C=CC(=O)C2=C1OC)O)O)C
• InChI: InChI=1S/C17H18O5/c1-9(2)4-5-11(18)10-8-14(21)15-12(19)6-7-13(20)16(15)17(10)22-3/h4,6-8,11,18,21H,5H2,1-3H3
• InChI Key: ILTIJHIVTUMMEE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₅
• Molecular Weight: 302.32 g/mol
• Exact Mass: 302.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.73
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7218	72.18%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7846	78.46%
OATP2B1 inhibitior	-	0.5826	58.26%
OATP1B1 inhibitior	+	0.9304	93.04%
OATP1B3 inhibitior	+	0.9111	91.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5639	56.39%
P-glycoprotein inhibitior	-	0.6894	68.94%
P-glycoprotein substrate	-	0.9168	91.68%
CYP3A4 substrate	+	0.5223	52.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8242	82.42%
CYP3A4 inhibition	-	0.7089	70.89%
CYP2C9 inhibition	+	0.5925	59.25%
CYP2C19 inhibition	+	0.7576	75.76%
CYP2D6 inhibition	+	0.5069	50.69%
CYP1A2 inhibition	+	0.8453	84.53%
CYP2C8 inhibition	-	0.8951	89.51%
CYP inhibitory promiscuity	+	0.6567	65.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8707	87.07%
Carcinogenicity (trinary)	Non-required	0.6863	68.63%
Eye corrosion	-	0.9907	99.07%
Eye irritation	+	0.5309	53.09%
Skin irritation	-	0.7557	75.57%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5119	51.19%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.5700	57.00%
skin sensitisation	-	0.6623	66.23%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7088	70.88%
Acute Oral Toxicity (c)	III	0.6747	67.47%
Estrogen receptor binding	+	0.8431	84.31%
Androgen receptor binding	-	0.5602	56.02%
Thyroid receptor binding	-	0.5532	55.32%
Glucocorticoid receptor binding	+	0.7543	75.43%
Aromatase binding	-	0.4843	48.43%
PPAR gamma	+	0.7404	74.04%
Honey bee toxicity	-	0.8358	83.58%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9891	98.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.62%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.30%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.83%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.67%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.86%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.39%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.06%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.60%	97.21%
CHEMBL4208	P20618	Proteasome component C5	82.91%	90.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.40%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	82.34%	94.73%
CHEMBL2535	P11166	Glucose transporter	81.47%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.22%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.00%	96.00%

Plants that contains it

• Onosma hispida

Cross-Links

• PubChem: 85101045
• LOTUS: LTS0003214
• wikiData: Q105115461