beta-Acetoxyisovalerylshikonin

Details

• Internal ID: a9af27c1-54f8-4712-be75-855a527a0dce
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-acetyloxy-3-methylbutanoate
• SMILES (Canonical): CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)CC(C)(C)OC(=O)C)C
• SMILES (Isomeric): CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)CC(C)(C)OC(=O)C)C
• InChI: InChI=1S/C23H26O8/c1-12(2)6-9-18(30-19(28)11-23(4,5)31-13(3)24)14-10-17(27)20-15(25)7-8-16(26)21(20)22(14)29/h6-8,10,18,25-26H,9,11H2,1-5H3/t18-/m1/s1
• InChI Key: BQSAGDWOHVQNFB-GOSISDBHSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₈
• Molecular Weight: 430.40 g/mol
• Exact Mass: 430.16276778 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.40
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• SCHEMBL5056231

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	-	0.6198	61.98%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8345	83.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	-	0.2848	28.48%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9328	93.28%
P-glycoprotein inhibitior	+	0.6844	68.44%
P-glycoprotein substrate	-	0.7552	75.52%
CYP3A4 substrate	+	0.5819	58.19%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.8511	85.11%
CYP2C9 inhibition	-	0.5073	50.73%
CYP2C19 inhibition	+	0.5480	54.80%
CYP2D6 inhibition	-	0.8871	88.71%
CYP1A2 inhibition	+	0.5904	59.04%
CYP2C8 inhibition	-	0.6669	66.69%
CYP inhibitory promiscuity	-	0.6269	62.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9012	90.12%
Carcinogenicity (trinary)	Non-required	0.6173	61.73%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.8439	84.39%
Skin irritation	-	0.7078	70.78%
Skin corrosion	-	0.9664	96.64%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7399	73.99%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.5695	56.95%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6893	68.93%
Acute Oral Toxicity (c)	III	0.5528	55.28%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.6229	62.29%
Thyroid receptor binding	+	0.6251	62.51%
Glucocorticoid receptor binding	+	0.8628	86.28%
Aromatase binding	+	0.5804	58.04%
PPAR gamma	+	0.7695	76.95%
Honey bee toxicity	-	0.8297	82.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL2581	P07339	Cathepsin D	98.19%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.02%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.97%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.74%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.08%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.57%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.56%	96.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.99%	96.09%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.66%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.65%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.57%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.04%	99.17%

Plants that contains it

• Alkanna tinctoria
• Arnebia euchroma
• Eucalyptus coccifera
• Lithospermum erythrorhizon
• Rhizomnium magnifolium

Cross-Links

• PubChem: 69295815
• NPASS: NPC152317
• LOTUS: LTS0049610
• wikiData: Q104944535