Akuammigine
PubChem CID
1268096
Structure
Molecular Formula
Synonyms
- akuammigine
- 642-17-1
- UNII-1E21YYE0UM
- 1E21YYE0UM
- CHEMBL122404
Molecular Weight
352.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-07-10
- Modify:2025-01-18
Description
Akuammigine is a monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from Vinca sardoa and Uncaria rhynchophylla. It has a role as a plant metabolite. It is a monoterpenoid indole alkaloid, a methyl ester and an organic heteropentacyclic compound.
Akuammigine has been reported in Uncaria tomentosa, Uncaria rhynchophylla, and other organisms with data available.
See also: Cat's Claw (part of).
Chemical Structure Depiction
methyl (1R,15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
GRTOGORTSDXSFK-BMYCAMMWSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C[C@H]1[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C21H24N2O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 19-epiajmalicine
- ajmalicine
- ajmalicine hydrochloride
- ajmalicine, (19alpha,20alpha)-isomer
- ajmalicine, (19beta)-isomer
- ajmalicine, (19beta,20alpha)-isomer
- ajmalicine, (3-beta,19beta)-isomer
- ajmalicine, (3beta,19alpha)-isomer
- ajmalicine, (3beta,19alpha,20alpha)-isomer
- ajmalicine, (hydrochloride(19beta,20alpha))-isomer
- ajmalicine, hydrochloride(19alpha)-isomer
- ajmalicine, PO4(19alpha)-isomer
- akuammigine
- delta-yohimbine
- Lamuran
- raubasine
- raubasine HCl
- raubasine hydrochloride
- rauvasan
- tetrahydro-alstonine
- tetrahydroalstonine
- akuammigine
- 642-17-1
- UNII-1E21YYE0UM
- 1E21YYE0UM
- CHEMBL122404
- 4H-Indolo(2,3-a)pyrano(3,4-g)quinolizine-1-carboxylic acid, 4a,5,7,8,13,13b,14,14a-octahydro-4-methyl-, methyl ester, (4S,4aS,13bR,14aS)-
- CHEBI:141878
- methyl (1R,15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
- Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (3beta,19alpha,20alpha)-
- methyl (3beta,19alpha,20alpha)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
- SCHEMBL563799
- GRTOGORTSDXSFK-BMYCAMMWSA-N
- DTXSID001318228
- HY-N2833
- BDBM50030622
- PDSP1_001665
- AKOS032948886
- FS-9280
- (3beta,20alpha)-16,17-Didehydro-19alpha-methyl-18-oxayohimban-16-carboxylic acid methyl ester
- DA-50297
- CS-0023407
- Q27252310
- (7aS,8S,11aS,12aR)-8-Methyl-5,6,7a,8,11a,12,12a,13-octahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester
- OXAYOHIMBAN-16-CARBOXYLIC ACID, 16,17-DIDEHYDRO-19-METHYL-, METHYL ESTER, (3.BETA.,19.ALPHA.,20.ALPHA.)-
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
352.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
352.17869263 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
352.17869263 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
54.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
26
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
606
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
353.186
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks
144.080154 100
143.072662 15.82
117.067345 14.89
145.083496 13.81
115.053787 10.97
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Cat's Claw (part of)
Vasodilator Agents
Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=GRTOGORTSDXSFK-BMYCAMMWSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Akuammiginehttps://www.wikidata.org/wiki/Q27252310LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- Japan Chemical Substance Dictionary (Nikkaji)
- Natural Product Activity and Species Source (NPASS)
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/about(7aS,8S,11aS,12aR)-8-Methyl-5,6,7a,8,11a,12,12a,13-octahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl esterhttps://pharos.nih.gov/ligands/6YFBSBFMLKDU
- SpectraBaseAKUAMMIGINEhttps://spectrabase.com/spectrum/Ig5TQIIPLs1
- Therapeutic Target Database (TTD)
- Thieme ChemistryLICENSEThe Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc-nd/4.0/
- Wikidataakuammiginehttps://www.wikidata.org/wiki/Q27252310
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlVasodilator Agentshttps://www.ncbi.nlm.nih.gov/mesh/68014665
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 394319250https://pubchem.ncbi.nlm.nih.gov/substance/394319250
CONTENTS