(1aR,7aS,10aS,10bS)-1a,5-dimethyl-8-methylidene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one

Details

• Internal ID: 40ec40cd-fb35-456e-abae-bd40cd2bad3c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
• SMILES (Canonical): CC1=CCCC2(C(O2)C3C(CC1)C(=C)C(=O)O3)C
• SMILES (Isomeric): C/C/1=C\CC[C@@]2([C@@H](O2)[C@@H]3[C@@H](CC1)C(=C)C(=O)O3)C
• InChI: InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1
• InChI Key: KTEXNACQROZXEV-SLXBATTESA-N
• Popularity: 1,424 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): 38.80 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.76
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• (-)-Parthenolide
• 20554-84-1
• (1aR,7aS,10aS,10bS)-1a,5-dimethyl-8-methylidene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
• DTXSID2040579
• NSC157035
• NSC-157035
• SCHEMBL8219
• MEGxp0_000050
• SCHEMBL5487404
• ACon1_001961
• Parthenolide ((-)-Parthenolide)
• 4,5-alpha-Epoxy-6-beta-hydroxygermacra-1(10),11(13)-dien-12-oic acid gamma-lactone
• 4,5alpha-epoxy-6beta-hydroxy-germacra-1(10),11(13)-dien-12-oic acid gamma-lactone
• CHEBI:181553
• KTEXNACQROZXEV-SLXBATTESA-N
• HMS3266B13
• HMS3411K04
• HMS3675K04
• Germacra-1(10),11(13)-dien-12-oic acid, 4,5.alpha.-epoxy-6.beta.-hydroxy-, .gamma.-lactone
• Oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one, 2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-, (1aR,4E,7aS,10aS,10bS)-
• Oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one, 2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-, [1aR-(1aR*,4E,7aS*,10aS*,10bR*)]-
• PTL
• s2341
• AKOS015969726
• AKOS022168211
• CCG-266943
• DB13063
• NCGC00024683-03
• NCGC00024683-20
• P1982
• C07609
• EN300-26868926
• SR-01000597658
• SR-01000597658-1
• BRD-K98548675-001-04-2
• Q63409339
• 4,5alpha-Epoxy-6beta-hydroxygermacra-1(10),11(13)-dien-12-oic Acid gamma-Lactone
• (1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0,2,4]tetradec-7-en-13-one
• (1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
• [1aR-(1aR*,4E,7aS*,10aS*,-10bR*)]-2,3-6,7,7a,8,10a,10b-Octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
• 503551-53-9
• Germacra-1(10),11(13)-dien-12-oic acid, 4,5.alpha.-epoxy-6.beta.-hydroxy-, gamma.-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.9067	90.67%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5903	59.03%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	-	0.9230	92.30%
P-glycoprotein inhibitior	-	0.8673	86.73%
P-glycoprotein substrate	-	0.8867	88.67%
CYP3A4 substrate	+	0.6041	60.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8455	84.55%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9348	93.48%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.5896	58.96%
CYP inhibitory promiscuity	-	0.9287	92.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5354	53.54%
Eye corrosion	-	0.9692	96.92%
Eye irritation	-	0.6890	68.90%
Skin irritation	-	0.5315	53.15%
Skin corrosion	-	0.8673	86.73%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3904	39.04%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.7320	73.20%
skin sensitisation	-	0.6307	63.07%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6742	67.42%
Acute Oral Toxicity (c)	III	0.4919	49.19%
Estrogen receptor binding	-	0.5491	54.91%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.5397	53.97%
Glucocorticoid receptor binding	+	0.6223	62.23%
Aromatase binding	-	0.7438	74.38%
PPAR gamma	-	0.5241	52.41%
Honey bee toxicity	-	0.7963	79.63%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9818	98.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4801	P29466	Caspase-1	10600 nM	Ki	PMID: 25418070
CHEMBL230	P35354	Cyclooxygenase-2	800 nM	IC50	PMID: 16038536
CHEMBL1293235	P02545	Prelamin-A/C	251.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.16%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.19%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.02%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.97%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.34%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.74%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.63%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.78%	95.89%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.67%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.32%	90.17%
CHEMBL2581	P07339	Cathepsin D	80.53%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.48%	93.40%

Plants that contains it

• Arctotis arctotoides
• Asteraceae
• Carpesium longifolium
• Cyathocline purpurea
• Lychnophora blanchetii
• Magnolia baillonii
• Magnolia champaca
• Magnolia compressa
• Magnolia grandiflora
• Magnolia rajaniana
• Rhodanthe stricta
• Tanacetum larvatum
• Tanacetum parthenium

Cross-Links

• PubChem: 6473881
• NPASS: NPC50362
• ChEMBL: CHEMBL540445
• LOTUS: LTS0201566
• wikiData: Q63409339