Chelidonine

Details

• Internal ID: b726928d-2412-4a4e-a2ab-c95baed7aef1
• Taxonomy: Alkaloids and derivatives > Benzophenanthridine alkaloids > Hexahydrobenzophenanthridine alkaloids
• IUPAC Name: (1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol
• SMILES (Canonical): CN1CC2=C(C=CC3=C2OCO3)C4C1C5=CC6=C(C=C5CC4O)OCO6
• SMILES (Isomeric): CN1CC2=C(C=CC3=C2OCO3)[C@@H]4[C@H]1C5=CC6=C(C=C5C[C@@H]4O)OCO6
• InChI: InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1
• InChI Key: GHKISGDRQRSCII-ZOCIIQOWSA-N
• Popularity: 402 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.40 g/mol
• Exact Mass: 353.12632271 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 2.20

Synonyms

• 476-32-4
• Stylophorin
• Chelidonin
• (+)-Chelidonine
• Khelidonin
• Helidonine
• Chelidoniny
• Stylophorine
• CHEBI:31389
• UNII-8K7EK8446J
• Chelidonin [German]
• Chelidoniny [Polish]
• 8K7EK8446J
• EINECS 207-504-1
• 4UDG3LY0GT
• CHELIDONINE (+)-FORM
• DTXSID10878474
• (+/-)-chelidonine
• (1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL, 5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL-, (5BR,6S,12BS)-
• (5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol
• CHELIDONINE (+)
• Chelidonine (+-)-
• UNII-4UDG3LY0GT
• NSC646661
• (1)-Chelidonine
• (1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL, 5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL-, (5BR,6S,12BS)-REL-
• [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-
• [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-rel-
• EINECS 243-662-8
• Prestwick0_000587
• Prestwick1_000587
• Prestwick2_000587
• Prestwick3_000587
• CHELIDONINE [INCI]
• BSPBio_000434
• CHELIDONINE [WHO-DD]
• DIPHYLLINE (ALKALOID)
• SCHEMBL563820
• SPBio_002653
• BPBio1_000478
• CHEMBL496867
• MEGxp0_001421
• Chelidonine ((+)-Chelidonine)
• ACon1_000007
• CHELIDONINE, (+/-)-
• GHKISGDRQRSCII-ZOCIIQOWSA-N
• DTXCID501016520
• HMS3886N18
• HY-N2369
• CHELIDONINE (+)-FORM [MI]
• Chelidonine, >=97.0% (HPLC)
• BDBM50480259
• MFCD00069660
• s9154
• AKOS016010202
• CCG-208430
• CHELIDONINE (+/-)-FORM [MI]
• NCGC00167959-01
• NCGC00167959-02
• NCGC00167959-03
• NCGC00167959-05
• NCGC00167959-12
• AC-34033
• MS-25483
• CS-0022550
• SR-05000002251
• Q-100506
• Q1069066
• SR-05000002251-2
• BRD-K32828673-001-01-5
• BRD-K32828673-002-03-9
• (1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol
• (5BR-(5B.ALPHA.,6.BETA.,12B.ALPHA.))-5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL(1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL
• (5BR-(5Balpha,6beta,12Balpha))-5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL(1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL
• 5b,6,7,12b,13,14-Hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenan-thridin-6-ol

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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.46%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.82%	96.77%
CHEMBL2581	P07339	Cathepsin D	93.91%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.79%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.61%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.60%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.96%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.07%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.01%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.70%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.05%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	82.91%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.52%	100.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.48%	80.96%
CHEMBL4208	P20618	Proteasome component C5	80.53%	90.00%

Plants that contains it

• Chelidonium majus
• Glaucium fimbrilligerum
• Glaucium flavum
• Haplophyllum acutifolium
• Sarcocapnos baetica
• Sarcocapnos crassifolia
• Sarcocapnos enneaphylla
• Stylophorum diphyllum
• Stylophorum lasiocarpum
• Symphoricarpos albus

Cross-Links

• PubChem: 197810
• NPASS: NPC294790
• ChEMBL: CHEMBL496867
• LOTUS: LTS0219440
• wikiData: Q1069066