Acetylshikonin

Details

• Internal ID: 3b7da721-3379-4325-ab11-bd500b21f8e0
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
• SMILES (Canonical): CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C)C
• SMILES (Isomeric): CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C)C
• InChI: InChI=1S/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3
• InChI Key: WNFXUXZJJKTDOZ-UHFFFAOYSA-N
• Popularity: 61 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.30 g/mol
• Exact Mass: 330.11033829 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 54984-93-9
• DL-Acetylshikonin
• 24502-78-1
• Shikonin, acetyl
• CHEBI:81069
• [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
• NSC 291844
• NSC-291844
• acetyl shikonin
• alkannin acetate
• 1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-
• Alkannin, monoacetate
• NSC 110199
• ARNEBIN 3
• ARNEBIN-3
• ALKANNIN MONOACETATE
• CHEMBL28569
• SCHEMBL1240671
• HY-N2181A
• WNFXUXZJJKTDOZ-UHFFFAOYSA-
• DTXSID30909976
• (+)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone 2-acetate
• 1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-, (R)-
• WNFXUXZJJKTDOZ-UHFFFAOYSA-N
• BCP18130
• NSC110199
• NSC140376
• NSC291844
• AKOS015896725
• NSC-140376
• 23444-71-5
• LS-95641
• CS-0368744
• B671806K005
• C17413
• Q27155025
• B2703-342008
• 1, 2-[1-(acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-
• 1, 2-[1-(acetyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-, (R)-
• 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, 2-acetate, (+)-
• 2-(1-acetyloxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinone
• 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate
• 106295-33-4
• InChI=1/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	+	0.5783	57.83%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8414	84.14%
OATP2B1 inhibitior	-	0.7178	71.78%
OATP1B1 inhibitior	+	0.9323	93.23%
OATP1B3 inhibitior	+	0.8085	80.85%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7715	77.15%
P-glycoprotein substrate	-	0.9231	92.31%
CYP3A4 substrate	-	0.5068	50.68%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.8377	83.77%
CYP2C9 inhibition	+	0.7155	71.55%
CYP2C19 inhibition	+	0.5930	59.30%
CYP2D6 inhibition	-	0.7088	70.88%
CYP1A2 inhibition	+	0.6540	65.40%
CYP2C8 inhibition	-	0.8442	84.42%
CYP inhibitory promiscuity	+	0.6283	62.83%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8822	88.22%
Carcinogenicity (trinary)	Non-required	0.6287	62.87%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.5819	58.19%
Skin irritation	-	0.7548	75.48%
Skin corrosion	-	0.9690	96.90%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6868	68.68%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.6151	61.51%
skin sensitisation	-	0.5474	54.74%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6882	68.82%
Acute Oral Toxicity (c)	III	0.6717	67.17%
Estrogen receptor binding	+	0.7150	71.50%
Androgen receptor binding	+	0.6482	64.82%
Thyroid receptor binding	-	0.6217	62.17%
Glucocorticoid receptor binding	+	0.7782	77.82%
Aromatase binding	-	0.6027	60.27%
PPAR gamma	+	0.7366	73.66%
Honey bee toxicity	-	0.8905	89.05%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
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	97.82%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.19%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.05%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.95%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.54%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.13%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.59%	99.15%

Plants that contains it

• Alkanna cappadocica
• Arnebia decumbens
• Arnebia euchroma
• Arnebia guttata
• Arnebia hispidissima
• Echium italicum
• Echium plantagineum
• Lithospermum erythrorhizon
• Onosma paniculata

Cross-Links

• PubChem: 32464
• NPASS: NPC68752
• LOTUS: LTS0056709
• wikiData: Q27155025