Butylshikonin

Details

• Internal ID: 271c11cf-73b0-4a93-9a4b-762dc4629b92
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] butanoate
• SMILES (Canonical): CCCC(=O)OC(CC=C(C)C)C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O
• SMILES (Isomeric): CCCC(=O)O[C@H](CC=C(C)C)C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O
• InChI: InChI=1S/C20H22O6/c1-4-5-17(24)26-16(9-6-11(2)3)12-10-15(23)18-13(21)7-8-14(22)19(18)20(12)25/h6-8,10,16,21-22H,4-5,9H2,1-3H3/t16-/m1/s1
• InChI Key: FMXUZLUFNDEQPM-MRXNPFEDSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.14163842 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.47
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] butanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.5464	54.64%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8160	81.60%
OATP2B1 inhibitior	-	0.7164	71.64%
OATP1B1 inhibitior	+	0.9085	90.85%
OATP1B3 inhibitior	+	0.8834	88.34%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8011	80.11%
P-glycoprotein inhibitior	-	0.6126	61.26%
P-glycoprotein substrate	-	0.8169	81.69%
CYP3A4 substrate	+	0.5229	52.29%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.7226	72.26%
CYP2C9 inhibition	+	0.5507	55.07%
CYP2C19 inhibition	+	0.6716	67.16%
CYP2D6 inhibition	-	0.7669	76.69%
CYP1A2 inhibition	+	0.7355	73.55%
CYP2C8 inhibition	-	0.6974	69.74%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8883	88.83%
Carcinogenicity (trinary)	Non-required	0.6683	66.83%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.6785	67.85%
Skin irritation	-	0.7892	78.92%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6887	68.87%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6600	66.00%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5405	54.05%
Acute Oral Toxicity (c)	III	0.5371	53.71%
Estrogen receptor binding	+	0.6274	62.74%
Androgen receptor binding	+	0.5727	57.27%
Thyroid receptor binding	-	0.5641	56.41%
Glucocorticoid receptor binding	+	0.7938	79.38%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8364	83.64%
Honey bee toxicity	-	0.8823	88.23%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
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
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.89%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.86%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.30%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.27%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.84%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.26%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.94%	99.17%
CHEMBL255	P29275	Adenosine A2b receptor	82.20%	98.59%

Plants that contains it

• Arnebia hispidissima
• Lithospermum erythrorhizon

Cross-Links

• PubChem: 10089766
• NPASS: NPC306835
• ChEMBL: CHEMBL8806
• LOTUS: LTS0106242
• wikiData: Q104998132