Artemin

Details

• Internal ID: 90c0ac0e-9218-45e8-a913-54aa5e7da683
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C2CCC3(C(CCC(=C)C3(C2OC1=O)O)O)C
• SMILES (Isomeric): CC1C2CCC3(C(CCC(=C)C3(C2OC1=O)O)O)C
• InChI: InChI=1S/C15H22O4/c1-8-4-5-11(16)14(3)7-6-10-9(2)13(17)19-12(10)15(8,14)18/h9-12,16,18H,1,4-7H2,2-3H3
• InChI Key: CJLHTKGWEUGORV-UHFFFAOYSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzofuran-2-one
• 6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-dodecahydronaphtho[1,2-b]furan-2-one
• 22149-38-8
• Artemine
• 11S-Artemin
• Artemin (sesquiterpene)
• Oprea1_752585
• MLS001195108
• CHEMBL1595875
• CHEBI:168328
• HMS1607C03
• HMS2864H06
• AKOS001483012
• AKOS021983219
• NCGC00245791-01
• SMR000554415
• (11a)-1b,5a-Dihydroxy-4(15)-eudesmen-12,6a-olide
• 6,9a-dihydroxy-3,5a-dimethyl-9-methylenedecahydronaphtho[1,2-b]furan-2(3H)-one
• [3S-(3alpha,3aalpha,5abeta,6beta,9aalpha,9bbeta)]-Decahydro-6,9a-dihydroxy-3,5a-dimethyl-9-methylenenaphtho[1,2-b]furan-2(3H)-one
• 6,9a-dihydroxy-3,5a-dimethyl-9-methylidene-3,3a,4,5,6,7,8,9b-octahydrobenzo[g][1]benzouran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9744	97.44%
Caco-2	+	0.5316	53.16%
Blood Brain Barrier	+	0.5527	55.27%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6535	65.35%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8824	88.24%
OATP1B3 inhibitior	+	0.8865	88.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6420	64.20%
BSEP inhibitior	-	0.9397	93.97%
P-glycoprotein inhibitior	-	0.9396	93.96%
P-glycoprotein substrate	-	0.8393	83.93%
CYP3A4 substrate	+	0.6168	61.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.6762	67.62%
CYP2C9 inhibition	-	0.9049	90.49%
CYP2C19 inhibition	-	0.8609	86.09%
CYP2D6 inhibition	-	0.9393	93.93%
CYP1A2 inhibition	-	0.7282	72.82%
CYP2C8 inhibition	-	0.9214	92.14%
CYP inhibitory promiscuity	-	0.9049	90.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5251	52.51%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9584	95.84%
Skin irritation	+	0.6199	61.99%
Skin corrosion	-	0.8962	89.62%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8275	82.75%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.7283	72.83%
skin sensitisation	-	0.8087	80.87%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5767	57.67%
Acute Oral Toxicity (c)	I	0.4497	44.97%
Estrogen receptor binding	+	0.7780	77.80%
Androgen receptor binding	+	0.6559	65.59%
Thyroid receptor binding	-	0.5119	51.19%
Glucocorticoid receptor binding	+	0.7632	76.32%
Aromatase binding	+	0.5373	53.73%
PPAR gamma	-	0.6714	67.14%
Honey bee toxicity	-	0.8475	84.75%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9920	99.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.61%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.11%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.00%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.86%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.62%	93.04%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.93%	96.09%
CHEMBL1871	P10275	Androgen Receptor	83.83%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.59%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.17%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.10%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	81.98%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.55%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	81.05%	91.49%

Plants that contains it

• Artemisia campestris subsp. campestris
• Artemisia giraldii
• Artemisia gmelinii
• Artemisia halophila
• Artemisia pontica
• Artemisia sericea
• Seriphidium caerulescens subsp. gallicum
• Seriphidium diffusum
• Seriphidium herba-alba
• Seriphidium ifranensis
• Seriphidium saissanicum
• Seriphidium turcomanicum
• Tanacetum cadmeum

Cross-Links

• PubChem: 3678270
• LOTUS: LTS0265485
• wikiData: Q104252396