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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24N2O4
Molecular Weight 368.4271
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PTEROPODINE

SMILES

C[C@@]1([H])[C@]2([H])CN3CC[C@@]4(c5ccccc5N=C4O)[C@]3([H])C[C@]2([H])C(=CO1)C(=O)OC

InChI

InChIKey=JMIAZDVHNCCPDM-QLMFUGSGSA-N
InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14-,18-,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H24N2O4
Molecular Weight 368.4271
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Pteropodine is a heterohimbine-type oxindole alkaloid specifically isolated from ‘Cat’s claw’ (Uncaria tomentosa), a plant that has shown cytostatic, anti-inflammatory and antimutagenic properties and is used in traditional medicine to cure a number of diseases. Pteropodine positively modulate the function of rat muscarinic M1 and 5-HT2 receptors expressed in Xenopus oocyte but further studies are necessary to elucidate the exact mechanism by which Pteropodine positively modulates muscarinic M1 and 5-HT2 receptor functions. Pteropodine reduced the sister-chromatid exchanges and micronucleated polychromatic erythrocytes production by doxorubicin in mouse, showing a protective effect on the in vivo DNA damage. Pteropodine exhibited a significant pro-apoptotic effect on Medullary thyroid carcinoma cells. Moreover, anti-proliferative effect of pteropodine was demonstrated on the acute lymphoblastic leukaemia cells and ovarian carcinoma cells.

Approval Year

PubMed

PubMed

TitleDatePubMed
Alkaloids and procyanidins of an Uncaria sp. from Peru.
1976 Jul
Two stereoisomeric pentacyclic oxindole alkaloids from Uncaria tomentosa: uncarine C and uncarine E.
2001 Apr
Investigation of Uña De Gato I. 7-Deoxyloganic acid and 15N NMR spectroscopic studies on pentacyclic oxindole alkaloids from Uncaria tomentosa.
2001 Jul
Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells.
2006 Mar
Patents

Sample Use Guides

Mice: 40 mg/kg
Route of Administration: Intraperitoneal
CEM-C7H2 cells were incubated for 24, 48 and 72 h with increasing concentrations (50–200 uM/l) of pteropodine. Dex, a standard chemotherapeutic agent for T-ALL cells, served as positive control. A dose of 50 uM/l pteropodine increased the sub-G1 population after 24 h by 31% compared with controls.
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:19:54 UTC 2021
Edited
by admin
on Sat Jun 26 10:19:54 UTC 2021
Record UNII
W24PZJ9QRZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PTEROPODINE
Common Name English
UNCARINE C
Common Name English
UNCARIN C
Common Name English
FORMOSANAN-16-CARBOXYLIC ACID, 19-METHYL-2-OXO-, METHYL ESTER, (19.ALPHA.,20.ALPHA.)
Common Name English
ALLO-PTEROPODINE
Common Name English
NSC-113093
Code English
PTEROPODIN
Common Name English
PTEROPOIDINE (UNCARINE C) (CONSTITUENT OF CAT'S CLAW) [DSC]
Common Name English
METHYL (19.ALPHA.,20.ALPHA.)-19-METHYL-2-OXOFORMOSANAN-16-CARBOXYLATE
Systematic Name English
Code System Code Type Description
CAS
5629-60-7
Created by admin on Sat Jun 26 10:19:54 UTC 2021 , Edited by admin on Sat Jun 26 10:19:54 UTC 2021
PRIMARY
PUBCHEM
10429112
Created by admin on Sat Jun 26 10:19:54 UTC 2021 , Edited by admin on Sat Jun 26 10:19:54 UTC 2021
PRIMARY
FDA UNII
W24PZJ9QRZ
Created by admin on Sat Jun 26 10:19:54 UTC 2021 , Edited by admin on Sat Jun 26 10:19:54 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Constituent of Uncaria tomentosa stem?s inner bark of Uncaria tomentosa stem.
PARENT -> CONSTITUENT ALWAYS PRESENT