Cheilanthifoline

Cheilanthifoline
Names
	IUPAC name 2-Methoxy-2′H-[1,3]dioxolo[4′,5′:9,10]berbin-3-ol
	Systematic IUPAC name (6aS)-9-Methoxy-6,6a,11,14-tetrahydro-2H,12H-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol
	Other names (S)-Cheilanthifoline
Identifiers
CAS Number	(S)-: 483-44-3 ;
3D model (JSmol)	rac: Interactive image ; (S)-: Interactive image ;
ChEBI	rac: CHEBI:140670 ; (S)-: CHEBI:16233 ;
ChemSpider	rac: 513559 ; (S)-: 62987502 ;
KEGG	(S)-: C05174 ;
PubChem CID	rac: 590762 ; (S)-: 101277425 ;
CompTox Dashboard (EPA)	rac: DTXSID70964044 ;
	InChI rac:InChI=1S/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3 Key: MKRKFSHHTKVRAR-UHFFFAOYSA-N; (S)-:InChI=1S/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1 Key: MKRKFSHHTKVRAR-HNNXBMFYSA-N;
	SMILES rac:COc1cc2c(cc1O)CCN3C2Cc4ccc5c(c4C3)OCO5; (S)-:COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O;
Properties
Chemical formula	C19H19NO4
Molar mass	325.364 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated March 18, 2025

(S)-Cheilanthifoline is a benzylisoquinoline alkaloid (BIA) which has been isolated from Corydalis dubia ^[1] and Argemone mexicana .^{[ citation needed ]} (S)-Cheilanthifoline is metabolically derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIAs. (S)-Cheilanthifoline is the immediate precursor of the BIA (S)-stylopine ((S)-stylopine synthase/CYP719A20), which is the precursor for the alkaloids protopine and sanguinarine.^[2]

References

↑ Wangchuk, P; Keller, PA; Pyne, SG; Willis, AC; Kamchonwongpaisan, S (2012). "Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia". Journal of Ethnopharmacology. 143 (1): 310–3. doi:10.1016/j.jep.2012.06.037. PMID 22796506.
↑ Hagel, Jillian; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Te (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15 (1): 227. Bibcode:2015BMCPB..15..227H. doi: 10.1186/s12870-015-0596-0 . PMC 4575454 . PMID 26384972.

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[1] Wangchuk, P; Keller, PA; Pyne, SG; Willis, AC; Kamchonwongpaisan, S (2012). "Antimalarial alkaloids from a Bhutanese traditional medicinal plant Corydalis dubia". Journal of Ethnopharmacology. 143 (1): 310–3. doi:10.1016/j.jep.2012.06.037. PMID 22796506.

[2] Hagel, Jillian; Morris, Jeremy S; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D; Chang, Limei; Chen, Xue; Farrow, Scott C; Zhang, Te (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biology. 15 (1): 227. Bibcode:2015BMCPB..15..227H. doi: 10.1186/s12870-015-0596-0 . PMC 4575454 . PMID 26384972.

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[2]

Names

IUPAC name 2-Methoxy-2′H-[1,3]dioxolo[4′,5′:9,10]berbin-3-ol
Systematic IUPAC name (6aS)-9-Methoxy-6,6a,11,14-tetrahydro-2H,12H-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol
Other names (S)-Cheilanthifoline
Identifiers
CAS Number	(S)-: 483-44-3
3D model (JSmol)	rac: Interactive image (S)-: Interactive image
ChEBI	rac: CHEBI:140670 (S)-: CHEBI:16233
ChemSpider	rac: 513559 (S)-: 62987502
KEGG	(S)-: C05174
PubChem CID	rac: 590762 (S)-: 101277425
CompTox Dashboard (EPA)	rac: DTXSID70964044
InChI rac:InChI=1S/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3 Key: MKRKFSHHTKVRAR-UHFFFAOYSA-N (S)-:InChI=1S/C19H19NO4/c1-22-18-8-13-12(7-16(18)21)4-5-20-9-14-11(6-15(13)20)2-3-17-19(14)24-10-23-17/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1 Key: MKRKFSHHTKVRAR-HNNXBMFYSA-N
SMILES rac:COc1cc2c(cc1O)CCN3C2Cc4ccc5c(c4C3)OCO5 (S)-:COC1=C(C=C2[C@@H]3CC4=C(CN3CCC2=C1)C5=C(C=C4)OCO5)O
Properties
Chemical formula	C₁₉H₁₉NO₄
Molar mass	325.364 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references