Dihydroshikonofuran

Details

• Internal ID: ac40bc68-0155-4d60-9b21-c89bc1cdfcab
• Taxonomy: Benzenoids > Phenols > Benzenediols > Hydroquinones
• IUPAC Name: 2-[4-(4-methylpent-3-enyl)-2,5-dihydrofuran-2-yl]benzene-1,4-diol
• SMILES (Canonical): CC(=CCCC1=CC(OC1)C2=C(C=CC(=C2)O)O)C
• SMILES (Isomeric): CC(=CCCC1=CC(OC1)C2=C(C=CC(=C2)O)O)C
• InChI: InChI=1S/C16H20O3/c1-11(2)4-3-5-12-8-16(19-10-12)14-9-13(17)6-7-15(14)18/h4,6-9,16-18H,3,5,10H2,1-2H3
• InChI Key: RLSJCCIBFMIPMJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.33 g/mol
• Exact Mass: 260.14124450 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.84
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEBI:81532
• C18135
• Q27155448

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.6736	67.36%
Blood Brain Barrier	+	0.5928	59.28%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8986	89.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8858	88.58%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7032	70.32%
P-glycoprotein inhibitior	-	0.9059	90.59%
P-glycoprotein substrate	-	0.7074	70.74%
CYP3A4 substrate	+	0.5357	53.57%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	+	0.3556	35.56%
CYP3A4 inhibition	+	0.6225	62.25%
CYP2C9 inhibition	+	0.5489	54.89%
CYP2C19 inhibition	+	0.5458	54.58%
CYP2D6 inhibition	-	0.8025	80.25%
CYP1A2 inhibition	+	0.8894	88.94%
CYP2C8 inhibition	-	0.6403	64.03%
CYP inhibitory promiscuity	+	0.9394	93.94%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8728	87.28%
Carcinogenicity (trinary)	Non-required	0.5916	59.16%
Eye corrosion	-	0.9717	97.17%
Eye irritation	-	0.6330	63.30%
Skin irritation	-	0.7173	71.73%
Skin corrosion	-	0.9055	90.55%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5763	57.63%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.5401	54.01%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7353	73.53%
Acute Oral Toxicity (c)	III	0.6977	69.77%
Estrogen receptor binding	+	0.6286	62.86%
Androgen receptor binding	-	0.5724	57.24%
Thyroid receptor binding	+	0.5849	58.49%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5475	54.75%
PPAR gamma	+	0.7571	75.71%
Honey bee toxicity	-	0.8917	89.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9878	98.78%

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	99.32%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	94.57%	95.93%
CHEMBL2581	P07339	Cathepsin D	94.08%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.81%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.59%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	89.55%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.76%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.13%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.36%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.21%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.68%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.88%	100.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.44%	99.15%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.79%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.47%	86.33%

Plants that contains it

• Lithospermum erythrorhizon

Cross-Links

• PubChem: 46174050
• LOTUS: LTS0261685
• wikiData: Q27155448