Shikonin acetate

Details

• Internal ID: 6694065f-1245-4361-ad40-716f99143cb0
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: [5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]-1,4-dioxo-3H-naphthalen-2-yl] acetate
• InChI: InChI=1S/C18H20O7/c1-9(2)4-7-14(23)18(25-10(3)19)8-13(22)15-11(20)5-6-12(21)16(15)17(18)24/h4-6,14,20-21,23H,7-8H2,1-3H3/t14-,18?/m1/s1
• InChI Key: MNGVKFABFGGTBC-IKJXHCRLSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₇
• Molecular Weight: 348.30 g/mol
• Exact Mass: 348.12090297 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.89
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	-	0.5717	57.17%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7454	74.54%
OATP2B1 inhibitior	-	0.7177	71.77%
OATP1B1 inhibitior	+	0.9209	92.09%
OATP1B3 inhibitior	+	0.8098	80.98%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7010	70.10%
P-glycoprotein inhibitior	-	0.8452	84.52%
P-glycoprotein substrate	-	0.8336	83.36%
CYP3A4 substrate	+	0.5267	52.67%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8544	85.44%
CYP3A4 inhibition	-	0.7245	72.45%
CYP2C9 inhibition	-	0.5807	58.07%
CYP2C19 inhibition	-	0.5652	56.52%
CYP2D6 inhibition	-	0.8537	85.37%
CYP1A2 inhibition	+	0.5158	51.58%
CYP2C8 inhibition	-	0.8491	84.91%
CYP inhibitory promiscuity	-	0.7092	70.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.6219	62.19%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.6257	62.57%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9474	94.74%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7251	72.51%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.6217	62.17%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6408	64.08%
Acute Oral Toxicity (c)	III	0.5593	55.93%
Estrogen receptor binding	-	0.5241	52.41%
Androgen receptor binding	+	0.6935	69.35%
Thyroid receptor binding	-	0.6587	65.87%
Glucocorticoid receptor binding	+	0.6680	66.80%
Aromatase binding	-	0.6991	69.91%
PPAR gamma	+	0.6467	64.67%
Honey bee toxicity	-	0.8440	84.40%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
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	98.60%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.45%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.62%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.94%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.80%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.02%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	85.09%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.52%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.40%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.01%	94.75%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.93%	85.30%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.53%	99.15%

Plants that contains it

• Arnebia decumbens

Cross-Links

• PubChem: 129650338
• LOTUS: LTS0272236
• wikiData: Q105168357