Shikonofuran A

Details

• Internal ID: 95e7e4cc-8e2b-4c4e-898b-bbe6fa71a362
• Taxonomy: Benzenoids > Phenols > Benzenediols > Hydroquinones
• IUPAC Name: [1-[5-(2,5-dihydroxyphenyl)furan-3-yl]-4-methylpent-3-enyl] acetate
• SMILES (Canonical): CC(=CCC(C1=COC(=C1)C2=C(C=CC(=C2)O)O)OC(=O)C)C
• SMILES (Isomeric): CC(=CCC(C1=COC(=C1)C2=C(C=CC(=C2)O)O)OC(=O)C)C
• InChI: InChI=1S/C18H20O5/c1-11(2)4-7-17(23-12(3)19)13-8-18(22-10-13)15-9-14(20)5-6-16(15)21/h4-6,8-10,17,20-21H,7H2,1-3H3
• InChI Key: IMZVJDUASUPZQK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.13107373 g/mol
• Topological Polar Surface Area (TPSA): 79.90 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.32
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 85022-66-8
• [1-[5-(2,5-dihydroxyphenyl)furan-3-yl]-4-methylpent-3-enyl] acetate
• AKOS037514887
• FT-0775866

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9916	99.16%
Caco-2	+	0.6654	66.54%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8522	85.22%
OATP2B1 inhibitior	-	0.5853	58.53%
OATP1B1 inhibitior	+	0.8860	88.60%
OATP1B3 inhibitior	+	0.8258	82.58%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6895	68.95%
P-glycoprotein inhibitior	-	0.5947	59.47%
P-glycoprotein substrate	-	0.8014	80.14%
CYP3A4 substrate	+	0.5583	55.83%
CYP2C9 substrate	-	0.5973	59.73%
CYP2D6 substrate	-	0.8345	83.45%
CYP3A4 inhibition	-	0.6982	69.82%
CYP2C9 inhibition	+	0.7173	71.73%
CYP2C19 inhibition	+	0.8374	83.74%
CYP2D6 inhibition	-	0.8822	88.22%
CYP1A2 inhibition	+	0.6946	69.46%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.8938	89.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8364	83.64%
Carcinogenicity (trinary)	Non-required	0.5193	51.93%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8390	83.90%
Skin irritation	-	0.7872	78.72%
Skin corrosion	-	0.9651	96.51%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6499	64.99%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.6657	66.57%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.5989	59.89%
Acute Oral Toxicity (c)	III	0.5622	56.22%
Estrogen receptor binding	+	0.7748	77.48%
Androgen receptor binding	+	0.7374	73.74%
Thyroid receptor binding	+	0.5945	59.45%
Glucocorticoid receptor binding	+	0.7355	73.55%
Aromatase binding	+	0.7313	73.13%
PPAR gamma	+	0.8341	83.41%
Honey bee toxicity	-	0.7916	79.16%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	+	0.9960	99.60%

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	96.75%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.33%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.50%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.03%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.60%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	90.79%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.70%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.22%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.01%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.63%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.20%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.71%	96.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.21%	90.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.38%	97.21%
CHEMBL3194	P02766	Transthyretin	81.85%	90.71%

Plants that contains it

• Lithospermum erythrorhizon

Cross-Links

• PubChem: 5321286
• NPASS: NPC225086
• LOTUS: LTS0093394
• wikiData: Q105116032