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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H23NO4
Molecular Weight 341.4009
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CORYPALMINE

SMILES

COC1=CC2=C(CCN3CC4=C(C[C@@H]23)C=CC(OC)=C4OC)C=C1O

InChI

InChIKey=BMCZTYDZHNTKPR-INIZCTEOSA-N
InChI=1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3/t16-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H23NO4
Molecular Weight 341.4009
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Corypalmine (or (-)-corypalmine) is an alkaloid which has been isolated from the crude base fraction of Corydalis chaerophylla and can inhibit prolyl oligopeptidase, an enzyme that hydrolyzes proline-containing peptides at the carboxy terminus of proline residues. It has been associated with schizophrenia, bipolar affective disorder, and related neuropsychiatric disorders and therefore may have important clinical implications.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P48147
Gene ID: 5550.0
Gene Symbol: PREP
Target Organism: Homo sapiens (Human)
128.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Application of BACE1 immobilized enzyme reactor for the characterization of multifunctional alkaloids from Corydalis cava (Fumariaceae) as Alzheimer's disease targets.
2016-03
Isoquinoline alkaloids as prolyl oligopeptidase inhibitors.
2015-06
7,7-Dimethylaporphine alkaloids from the stem of Guatteriopsis friesiana.
2009-08
New alkaloids from Corydalis species.
2009
Efficacy of alkaloid (-)-corypalmine against spore germination of some fungi.
2002
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Inhibition activity of the alkaloid (-)-corypalmine on spore germination of plant pathogenic and saprophytic fungi (Alternaria solani, A brassicicola, A. brassicae, A. melongenae, Curvularia pallescens, C. lunata, C. maculans, Curvularisa sp., Colletotrichum sp., Helminthosporium speciferum, H. frumentacei, H. pennisetti, Heterosporium sp., Penicillum sp., Ustilago cynodontis) was determined. Spore germination of all the tested fungi was inhibited, Heterosporium sp. and Ustilago cynodontis being the most sensitive (complete inhibition of spore germination was observed at the very low concentration of 200 ppm). Curvularia palliscens, C. maculans and Curvularia sp. were less sensitive; complete inhibition of spore germination occurred at 400 ppm.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:23:52 GMT 2025
Edited
by admin
on Mon Mar 31 21:23:52 GMT 2025
Record UNII
28R31624GX
Record Status Validated (UNII)
Record Version
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Name Type Language
CORYPALMINE
MI  
Common Name English
(-)-CORYPALMINE
Preferred Name English
CORYPALMINE, (-)-
Common Name English
L-TETRAHYDROJATRORRHIZINE
Common Name English
3-HYDROXY-2,9,10-TRIMETHOXY-13A.ALPHA.-BERBINE
Common Name English
(13AS)-5,8,13,13A-TETRAHYDRO-2,9,10-TRIMETHOXY-6H-DIBENZO(A,G)QUINOLIZIN-3-OL
Systematic Name English
CORYPALMINE [MI]
Common Name English
CORYPALMINE L-FORM [MI]
Common Name English
(S)-TETRAHYDROJATRORRHIZINE
Common Name English
DISCRETININE
Common Name English
6H-DIBENZO(A,G)QUINOLIZIN-3-OL, 5,8,13,13A-TETRAHYDRO-2,9,10-TRIMETHOXY-, (13AS)-
Systematic Name English
CORYPALMIN
Common Name English
Code System Code Type Description
MERCK INDEX
m3806
Created by admin on Mon Mar 31 21:23:52 GMT 2025 , Edited by admin on Mon Mar 31 21:23:52 GMT 2025
PRIMARY Merck Index
PUBCHEM
11186895
Created by admin on Mon Mar 31 21:23:52 GMT 2025 , Edited by admin on Mon Mar 31 21:23:52 GMT 2025
PRIMARY
MERCK INDEX
m3806
Created by admin on Mon Mar 31 21:23:52 GMT 2025 , Edited by admin on Mon Mar 31 21:23:52 GMT 2025
PRIMARY Merck Index
CAS
6018-40-2
Created by admin on Mon Mar 31 21:23:52 GMT 2025 , Edited by admin on Mon Mar 31 21:23:52 GMT 2025
PRIMARY
FDA UNII
28R31624GX
Created by admin on Mon Mar 31 21:23:52 GMT 2025 , Edited by admin on Mon Mar 31 21:23:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID00975603
Created by admin on Mon Mar 31 21:23:52 GMT 2025 , Edited by admin on Mon Mar 31 21:23:52 GMT 2025
PRIMARY