Cnicin

Details

• Internal ID: aa189a37-3756-49a3-8e4f-534014e2a009
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate
• SMILES (Canonical): CC1=CCCC(=CC2C(C(C1)OC(=O)C(=C)C(CO)O)C(=C)C(=O)O2)CO
• SMILES (Isomeric): C/C/1=C\CC/C(=C/[C@@H]2[C@@H]([C@H](C1)OC(=O)C(=C)[C@H](CO)O)C(=C)C(=O)O2)/CO
• InChI: InChI=1S/C20H26O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8,15-18,21-23H,2-4,6-7,9-10H2,1H3/b11-5+,14-8-/t15-,16-,17+,18+/m0/s1
• InChI Key: ZTDFZLVUIVPZDU-QGNHJMHWSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.16785316 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.20

Synonyms

• 24394-09-0
• C998MWY30L
• Centaurin
• Cynisin
• Cnicine
• UNII-C998MWY30L
• EINECS 246-221-8
• C09362
• CNICIN [MI]
• SCHEMBL1869092
• DTXSID90878518
• AKOS040760342
• HY-137984
• CS-0143484
• Q5137363
• (3R)-3,4-DIHYDROXY-2-METHYLENEBUTANOIC ACID (3AR,4S,6E,10Z,11AR)-2,3,3A,4,5,8,9,11A-OCTAHYDRO-10-(HYDROXYMETHYL)-6-METHYL-3-METHYLENE-2-OXOCYCLODECA(B)FURAN-4-YL ESTER
• (Z,E)-6.ALPHA.,8.ALPHA.,15-TRIHYDROXYGERMACRA-1(10),4,11(13)-TRIEN-12-OIC ACID 12,6-LACTONE 8-(3,4-DIHYDROXY-2-METHYLENEBUTYRATE)
• 2,3,3a,4,5,8,9,11a-Octahydro-10-(hydroxymethyl)-6-methyl-3-methylene-2-oxocyclodeca(b)furan-4-yl 3,4-dihydroxy-2-methylenebutyrate
• Butanoic acid, 3,4-dihydroxy-2-methylene-, 2,3,3a,4,5,8,9,11a-octahydro-10-(hydroxymethyl)-6-methyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4S*(R*),6E,10Z,11aR*))-
• Germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha,8-alpha,15-trihydroxy-, 12,6-lactone, 8-(3,4-dihydroxy-2-methylenebutyrate)

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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.53%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.58%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.02%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.90%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.48%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.74%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.80%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	83.54%	83.82%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.42%	96.47%
CHEMBL3401	O75469	Pregnane X receptor	82.91%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.97%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.91%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.21%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.20%	98.75%

Plants that contains it

• Centaurea aegialophila
• Centaurea affinis
• Centaurea alba
• Centaurea alexandrina
• Centaurea arenaria
• Centaurea calcitrapa
• Centaurea cineraria
• Centaurea cuneifolia
• Centaurea deusta
• Centaurea diffusa
• Centaurea napifolia
• Centaurea orphanidea
• Centaurea pallescens
• Centaurea paniculata
• Centaurea paui
• Centaurea sphaerocephala
• Centaurea spinosa
• Centaurea sulphurea
• Centaurea thessala
• Centaurea virgata subsp. squarrosa

Cross-Links

• PubChem: 5281435
• LOTUS: LTS0237446
• wikiData: Q5137363