arteminorin C

Details

• Internal ID: a0b942e5-dd7d-4ef4-b4a6-2e6f62aaa691
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 6,7-dihydroxycoumarins
• IUPAC Name: 3-(6,7-dihydroxy-2-oxochromen-3-yl)-7-hydroxy-6,8-dimethoxychromen-2-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)C=C(C(=O)O2)C3=CC4=CC(=C(C=C4OC3=O)O)O)OC)O
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)C=C(C(=O)O2)C3=CC4=CC(=C(C=C4OC3=O)O)O)OC)O
• InChI: InChI=1S/C20H14O9/c1-26-15-6-9-4-11(20(25)29-17(9)18(27-2)16(15)23)10-3-8-5-12(21)13(22)7-14(8)28-19(10)24/h3-7,21-23H,1-2H3
• InChI Key: XFGGVXYNIBUVBK-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₄O₉
• Molecular Weight: 398.30 g/mol
• Exact Mass: 398.06378202 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• CHEMBL1085430
• BDBM50310442

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8441	84.41%
Caco-2	-	0.7219	72.19%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7992	79.92%
OATP2B1 inhibitior	-	0.5658	56.58%
OATP1B1 inhibitior	+	0.9080	90.80%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4762	47.62%
P-glycoprotein inhibitior	+	0.6097	60.97%
P-glycoprotein substrate	-	0.7841	78.41%
CYP3A4 substrate	+	0.5279	52.79%
CYP2C9 substrate	-	0.8321	83.21%
CYP2D6 substrate	-	0.8219	82.19%
CYP3A4 inhibition	-	0.8871	88.71%
CYP2C9 inhibition	-	0.7617	76.17%
CYP2C19 inhibition	-	0.8000	80.00%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.7545	75.45%
CYP2C8 inhibition	-	0.6423	64.23%
CYP inhibitory promiscuity	-	0.8167	81.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6040	60.40%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.5980	59.80%
Skin irritation	-	0.7325	73.25%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7357	73.57%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9382	93.82%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7423	74.23%
Acute Oral Toxicity (c)	III	0.4789	47.89%
Estrogen receptor binding	+	0.9178	91.78%
Androgen receptor binding	+	0.7959	79.59%
Thyroid receptor binding	+	0.5960	59.60%
Glucocorticoid receptor binding	+	0.8113	81.13%
Aromatase binding	-	0.5749	57.49%
PPAR gamma	+	0.7796	77.96%
Honey bee toxicity	-	0.8788	87.88%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9515	95.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1929	P47989	Xanthine dehydrogenase	7710 nM	IC50	PMID: 19476336

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.75%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.75%	94.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	94.35%	98.11%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	92.96%	80.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.73%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.31%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.95%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.40%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.56%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.88%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.26%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.94%	94.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.14%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.95%	96.21%
CHEMBL2535	P11166	Glucose transporter	82.03%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	80.83%	90.20%

Plants that contains it

• Artemisia minor
• Bulbophyllum crabro
• Dioscorea gracillima
• Echium rubrum
• Entada africana
• Entada polystachya
• Fumaria indica
• Iberis sempervirens
• Plectranthus verticillatus
• Pontederia crassipes
• Pseuduvaria trimera
• Pteris spinescens
• Roemeria carica
• Schumanniophyton magnificum
• Vitex limonifolia

Cross-Links

• PubChem: 44178672
• NPASS: NPC48366
• ChEMBL: CHEMBL1085430
• LOTUS: LTS0222254
• wikiData: Q105327011