Atractylenolide III

Details

• Internal ID: 3aee79ce-6acc-4650-9513-8f09004d51f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2CC3C(=C)CCCC3(CC2(OC1=O)O)C
• SMILES (Isomeric): CC1=C2C[C@H]3C(=C)CCC[C@@]3(C[C@@]2(OC1=O)O)C
• InChI: InChI=1S/C15H20O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h11,17H,1,4-8H2,2-3H3/t11-,14+,15-/m0/s1
• InChI Key: FBMORZZOJSDNRQ-GLQYFDAESA-N
• Popularity: 96 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.70
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 73030-71-4
• AtractylenolideIII
• Codonolactone
• 8beta-Hydroxyasterolide
• 8-Hydroxyasterolide
• CHEMBL486961
• CHEBI:69958
• HSDB 8108
• (4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• Naphtho(2,3-b)furan-2(4H)-one, 4a,5,6,7,8,8a,9,9a-octahydro-9a-hydroxy-3,8a-dimethyl-5-methylene-, (4aS,8aR,9aS)-
• Naphtho[2,3-b]furan-2(4H)-one,4a,5,6,7,8,8a,9,9a-octahydro-9a-hydroxy-3,8a-dimethyl-5-methylene-,(4aS,8aR,9aS)-
• Icodonolactone
• Atractylenolide beta
• Atractylenolide-III
• atractylenolide cento
• 8b-Hydroxyasterolide
• Atractylodes japonica
• MFCD00238543
• SCHEMBL19082784
• DTXSID50223308
• ICodonolactone;8-Hydroxyasterolide
• BCP18761
• HY-N0203
• BDBM50241945
• s9313
• AKOS015897171
• Atractylenolide III, >=98% (HPLC)
• CCG-266941
• CS-3671
• NCGC00385304-01
• AC-34013
• AS-77621
• C17887
• Q-100798
• Q27138303
• Z3234884883
• (4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one
• (4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one
• aphtho[2,3-b]furan-2(4H)-one, 4a,5,6,7,8,8a,9,9a-octahydro-9a-hydroxy-3,8a-dimethyl-5-methylene-, (4aS,8aR,9aS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.8305	83.05%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7052	70.52%
OATP2B1 inhibitior	-	0.8525	85.25%
OATP1B1 inhibitior	+	0.8723	87.23%
OATP1B3 inhibitior	+	0.9266	92.66%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.6151	61.51%
BSEP inhibitior	-	0.8591	85.91%
P-glycoprotein inhibitior	-	0.9081	90.81%
P-glycoprotein substrate	-	0.9085	90.85%
CYP3A4 substrate	+	0.5995	59.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8755	87.55%
CYP3A4 inhibition	-	0.5769	57.69%
CYP2C9 inhibition	-	0.8854	88.54%
CYP2C19 inhibition	-	0.7219	72.19%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.6139	61.39%
CYP2C8 inhibition	-	0.8653	86.53%
CYP inhibitory promiscuity	-	0.9165	91.65%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4626	46.26%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.7379	73.79%
Skin irritation	+	0.6002	60.02%
Skin corrosion	-	0.9009	90.09%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4012	40.12%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6900	69.00%
skin sensitisation	-	0.7371	73.71%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.5364	53.64%
Acute Oral Toxicity (c)	III	0.3566	35.66%
Estrogen receptor binding	-	0.7109	71.09%
Androgen receptor binding	+	0.6459	64.59%
Thyroid receptor binding	+	0.6532	65.32%
Glucocorticoid receptor binding	+	0.5914	59.14%
Aromatase binding	-	0.5842	58.42%
PPAR gamma	-	0.5371	53.71%
Honey bee toxicity	-	0.8948	89.48%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9946	99.46%

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	94.22%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.15%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.53%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.73%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.09%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.12%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.02%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.27%	93.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.68%	96.09%

Plants that contains it

• Actinidia chinensis var. deliciosa
• Atractylodes lancea
• Atractylodes macrocephala
• Chloranthus henryi
• Chloranthus tianmushanensis
• Codonopsis pilosula
• Codonopsis subglobosa
• Lepidium apetalum
• Lindera aggregata
• Papaver bracteatum
• Papaver somniferum
• Tetradium glabrifolium
• Trattinnickia aspera

Cross-Links

• PubChem: 155948
• NPASS: NPC10636
• LOTUS: LTS0024642
• wikiData: Q27138303