Tussilagone

Details

• Internal ID: 31f99094-da74-4fb2-b168-01223a7f14bc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,3aR,5R,7S,7aS)-1-[(1R)-1-acetyloxyethyl]-4-methylidene-2-oxo-7-propan-2-yl-3,3a,5,6,7,7a-hexahydro-1H-inden-5-yl] (E)-3-methylpent-2-enoate
• SMILES (Canonical): CCC(=CC(=O)OC1CC(C2C(C1=C)CC(=O)C2C(C)OC(=O)C)C(C)C)C
• SMILES (Isomeric): CC/C(=C/C(=O)O[C@@H]1C[C@H]([C@H]2[C@H](C1=C)CC(=O)[C@@H]2[C@@H](C)OC(=O)C)C(C)C)/C
• InChI: InChI=1S/C23H34O5/c1-8-13(4)9-21(26)28-20-11-17(12(2)3)23-18(14(20)5)10-19(25)22(23)15(6)27-16(7)24/h9,12,15,17-18,20,22-23H,5,8,10-11H2,1-4,6-7H3/b13-9+/t15-,17+,18+,20-,22+,23+/m1/s1
• InChI Key: CFUPNMDNSQIWBB-UUVDBSHOSA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.50 g/mol
• Exact Mass: 390.24062418 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 4.10

Synonyms

• 104012-37-5
• 95N0GBB2SX
• DTXSID801318139
• (7R,14R)-14-Acetoxy-7-((2'E)-3'-methylpent-2'-enoyloxy)-oplopanone
• L-652469
• RefChem:50674
• 14-acetoxy-7B-(3'-ethylcrotonoyloxy)-notonipetranone
• L-652,469
• DTXCID101747927
• oplopanone, (7R,14R)-14-acetoxy-7-((2E)-3'-methylpent-2'-enoyloxy)-
• 2-Pentenoic acid, 3-methyl-, 1-(1-(acetyloxy)ethyl)octahydro-4-methylene-7-(1-methylethyl)-2-oxo-1H-inden-5-yl ester, (1S-(1alpha(S*),3abeta,5beta(E),7alpha,7aalpha))-
• UNII-95N0GBB2SX
• (1S,3aR,5R,7S,7aS)-1-((R)-1-Acetoxyethyl)-7-isopropyl-4-methylene-2-oxooctahydro-1H-inden-5-yl (E)-3-methylpent-2-enoate
• [(1S,3Ar,5R,7S,7aS)-1-[(1R)-1-acetyloxyethyl]-4-methylidene-2-oxo-7-propan-2-yl-3,3a,5,6,7,7a-hexahydro-1H-inden-5-yl] (E)-3-methylpent-2-enoate
• Tussilagone (Standard)
• orb1300232
• SCHEMBL29384573
• HY-N1388R
• HY-N1388
• MSK159651
• AKOS040759061
• CCG-268534
• EBC-617099
• (1S,3aR,5R,7S,7aS)-1-[(1R)-1-(acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate
• AC-34378
• DA-68420
• MS-26511
• CS-0016808
• S9180
• Q27271803
• Tussilagone(7R,14R)-14-Acetoxy-7-((2'E)-3'-methylpent-2'-enoyloxy)-oplopanone
• (1S,3aR,5R,7S,7aS)-1-[(1R)-1-(Acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate
• 2-PENTENOIC ACID, 3-METHYL-, (1S,3AR,5R,7S,7AS)-1-((1R)-1-(ACETYLOXY)ETHYL)OCTAHYDRO-4-METHYLENE-7-(1-METHYLETHYL)-2-OXO-1H-INDEN-5-YL ESTER, (2E)-
• 2-Pentenoic acid, 3-methyl-, 1-(1-(acetyloxy)ethyl)octahydro-4-methylene-7-(1-methylethyl)-2-oxo-1H-inden-5-yl ester, (1S-(1-alpha(S*),3a-beta,5-beta(E),7-alpha,7a-alpha))-
• 2-PENTENOIC ACID, 3-METHYL-, 1-(1-(ACETYLOXY)ETHYL)OCTAHYDRO-4-METHYLENE-7-(1-METHYLETHYL)-2-OXO-1H-INDEN-5-YL ESTER, (1S-(1.ALPHA.(S*),3A.BETA.,5.BETA.(E),7.ALPHA.,7A.ALPHA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.25%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.90%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.27%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.02%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.27%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.69%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.42%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.87%	89.34%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.86%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	86.72%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.71%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.44%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.43%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.57%	89.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.08%	94.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.59%	89.50%

Plants that contains it

• Parasenecio petasitoides

Cross-Links

• PubChem: 13919185
• LOTUS: LTS0192080
• wikiData: Q27271803