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rescinnamine   Click here for help

GtoPdb Ligand ID: 7098

Approved drug
rescinnamine is an approved drug
Compound class: Natural product
Comment: Rescinnamine is an angiotensin-converting enzyme (ACE) inhibitor. There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 117.78
Molecular weight 634.29
XLogP 3.9
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1ccc2c(c1)[nH]c1c2CCN2C1CC1C(C2)CC(C(C1C(=O)OC)OC)OC(=O)C=Cc1cc(OC)c(c(c1)OC)OC
Isomeric SMILES COc1ccc2c(c1)[nH]c1c2CCN2[C@@H]1C[C@H]1[C@@H](C2)C[C@H]([C@@H]([C@H]1C(=O)OC)OC)OC(=O)/C=C/c1cc(OC)c(c(c1)OC)OC
InChI InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1
InChI Key SZLZWPPUNLXJEA-QEGASFHISA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes.
IUPAC Name Click here for help
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
International Nonproprietary Names Click here for help
INN number INN
683 rescinnamine
Database Links Click here for help
CAS Registry No. 24815-24-5
ChEBI CHEBI:28572
ChEMBL Ligand CHEMBL1668
DrugBank Ligand DB01180
DrugCentral Ligand 2369
GtoPdb PubChem SID 178103676
PubChem CID 5280954
Search Google for chemical match using the InChIKey SZLZWPPUNLXJEA-QEGASFHISA-N
Search Google for chemicals with the same backbone SZLZWPPUNLXJEA
Search PubMed clinical trials rescinnamine
Search PubMed titles rescinnamine
Search PubMed titles/abstracts rescinnamine
UniChem Compound Search for chemical match using the InChIKey SZLZWPPUNLXJEA-QEGASFHISA-N
UniChem Connectivity Search for chemical match using the InChIKey SZLZWPPUNLXJEA-QEGASFHISA-N
Wikipedia Rescinnamine