U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H39N3O2
Molecular Weight 461.6389
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ECHINULINE

SMILES

C[C@@H]1NC(=O)[C@H](CC2=C(NC3=C(CC=C(C)C)C=C(CC=C(C)C)C=C23)C(C)(C)C=C)NC1=O

InChI

InChIKey=DIKMWTRJIZQJMY-CYFREDJKSA-N
InChI=1S/C29H39N3O2/c1-9-29(7,8)26-23(16-24-28(34)30-19(6)27(33)31-24)22-15-20(12-10-17(2)3)14-21(25(22)32-26)13-11-18(4)5/h9-11,14-15,19,24,32H,1,12-13,16H2,2-8H3,(H,30,34)(H,31,33)/t19-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula C29H39N3O2
Molecular Weight 461.6389
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Echinulin is an alkaloid isolated from the fungal extract, which inhibits the protein-tyrosine phosphatase 1B (PTP1B) and can be further investigated for the treatment of diabetes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
29.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Natural antimycobacterial metabolites: current status.
2004 Apr

Sample Use Guides

in mice: Twenty eight albino mice were fasted for 12 h prior to induction of hyperglycemia. Diabetes was induced using freshly prepared solution of alloxan monohydrate (i.p. at 120 mg/kg body weight). After the induction, the diabetic animals were randomly divided into seven groups (n = 4) and treated orally according to the following protocols: Group B: alloxan +20 mg/kg of 1/2 Compounds echinulin (1) and arestrictin B (2), (or 1/2), two isomeric indole-containing diketopiperazine alkaloids, were obtained as a mixture (56:54). They were thus evaluated as one sample.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:43:23 GMT 2023
Edited
by admin
on Fri Dec 15 19:43:23 GMT 2023
Record UNII
3DP19VPN8U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ECHINULINE
MI  
Common Name English
ECHINULINE [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m4816
Created by admin on Fri Dec 15 19:43:23 GMT 2023 , Edited by admin on Fri Dec 15 19:43:23 GMT 2023
PRIMARY Merck Index
FDA UNII
3DP19VPN8U
Created by admin on Fri Dec 15 19:43:23 GMT 2023 , Edited by admin on Fri Dec 15 19:43:23 GMT 2023
PRIMARY
MESH
C001132
Created by admin on Fri Dec 15 19:43:23 GMT 2023 , Edited by admin on Fri Dec 15 19:43:23 GMT 2023
PRIMARY
CAS
1859-87-6
Created by admin on Fri Dec 15 19:43:23 GMT 2023 , Edited by admin on Fri Dec 15 19:43:23 GMT 2023
PRIMARY
PUBCHEM
115252
Created by admin on Fri Dec 15 19:43:23 GMT 2023 , Edited by admin on Fri Dec 15 19:43:23 GMT 2023
PRIMARY