Alantolactone

Details

• Internal ID: eb521ef5-5e11-46c0-b290-b90defc97e6d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCCC2(C1=CC3C(C2)OC(=O)C3=C)C
• SMILES (Isomeric): C[C@H]1CCC[C@]2(C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)C
• InChI: InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1
• InChI Key: PXOYOCNNSUAQNS-AGNJHWRGSA-N
• Popularity: 459 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.24
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• helenine
• 546-43-0
• helenin
• Eupatal
• Alant camphor
• Inula camphor
• Elecampane camphor
• CHEBI:2540
• AI3-31147
• NSC93131
• EINECS 208-899-3
• NSC 93131
• UNII-M7GSN5Q1M6
• NSC 302289
• M7GSN5Q1M6
• CHEMBL136356
• NSC-93131
• (3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one
• (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one
• Alantic anhydride
• 4alphaH-Eudesma-5,11(13)-dien-12-oic acid, 8beta-hydroxy-, gamma-lactone
• (3AR-(3aalpha,5beta,8abeta,9aalpha))-3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylenenaphtho(2,3-b)furan-2(3H)-one
• Naphtho(2,3-b)furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR-(3a alpha,5beta,8a beta,9a alpha))-
• Alantcamphor
• [3aR-(3aalpha,5beta,8abeta,9aalpha)]-3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one
• Spectrum_000297
• (+)-Alantolactone; Alant camphor; Inula camphor
• Spectrum2_000297
• Spectrum3_001358
• Spectrum4_001772
• Spectrum5_000383
• ALANTOLACTONE [MI]
• Epitope ID:119691
• BSPBio_003175
• KBioGR_002284
• KBioSS_000777
• SPECTRUM310010
• SCHEMBL155169
• SPBio_000234
• KBio2_000777
• KBio2_003345
• KBio2_005913
• KBio3_002395
• DTXSID90877864
• Alantolactone, >=98% (HPLC)
• HY-N0038
• BDBM50096873
• CCG-39639
• s8318
• AKOS015906135
• CS-3595
• LMPR0103190013
• SDCCGMLS-0066583.P001
• NCGC00178225-01
• NCGC00178225-02
• NCGC00178225-05
• (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f]benzofuran-2-one
• AC-31414
• BS-17042
• LS-95330
• NCI60_042073
• C09289
• Q21099633
• 4.alpha.H-Eudesma-5, 8.beta.-hydroxy-, .gamma.-lactone
• 8-beta-hydroxy-4-alpha H-eudesm-5-en-12-oic acid gamma-lactone
• 8.BETA.-HYDROXY-4.ALPHA.H-EUDESM-5-EN-12-OIC ACID .GAMMA.-LACTONE
• (3aR,5S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one
• [3aR-(3a alpha,5 beta,8a beta,9a alpha)]-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one
• Naphtho(2,3-b)furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR-(3aalpha,5beta,8abeta,9aalpha))-
• Naphtho[2, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, [3aR-(3a.alpha.,5.beta.,8a.beta.,9a.alpha.)]-
• Naphtho[2,3-b]furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR,5S,8aR,9aR)-
• Naphtho[2,3-b]furan-2(3H)-one,3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-,(3aR,5S,8aR,9aR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8861	88.61%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4760	47.60%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.8809	88.09%
OATP1B3 inhibitior	+	0.9186	91.86%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.9450	94.50%
P-glycoprotein inhibitior	-	0.8808	88.08%
P-glycoprotein substrate	-	0.8813	88.13%
CYP3A4 substrate	+	0.5837	58.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	+	0.5078	50.78%
CYP2C9 inhibition	-	0.9487	94.87%
CYP2C19 inhibition	+	0.6954	69.54%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	+	0.7753	77.53%
CYP2C8 inhibition	-	0.7843	78.43%
CYP inhibitory promiscuity	-	0.8149	81.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4703	47.03%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.6676	66.76%
Skin irritation	+	0.4897	48.97%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6798	67.98%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6671	66.71%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5263	52.63%
Acute Oral Toxicity (c)	III	0.7603	76.03%
Estrogen receptor binding	-	0.6156	61.56%
Androgen receptor binding	-	0.5463	54.63%
Thyroid receptor binding	-	0.5241	52.41%
Glucocorticoid receptor binding	+	0.5505	55.05%
Aromatase binding	-	0.5938	59.38%
PPAR gamma	-	0.6272	62.72%
Honey bee toxicity	-	0.8547	85.47%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.9959	99.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.76%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.55%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.88%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.22%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.58%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.76%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	84.69%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.44%	82.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.02%	92.94%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.15%	93.03%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.76%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.83%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.58%	97.14%

Plants that contains it

• Abutilon indicum
• Ajania fruticulosa
• Aucklandia costus
• Bidens subalternans
• Chrysanthemum morifolium
• Dittrichia viscosa subsp. viscosa
• Eupatorium cannabinum
• Flourensia macrophylla
• Geigeria aspera
• Inula helenium
• Inula japonica
• Inula magnifica
• Inula racemosa
• Inula royleana
• Klasea latifolia
• Spilanthes leiocarpa
• Tanacetum parthenium
• Telekia speciosa

Cross-Links

• PubChem: 72724
• NPASS: NPC178676
• ChEMBL: CHEMBL136356
• LOTUS: LTS0175223
• wikiData: Q21099633