Euscaphic Acid
PubChem CID
471426
Structure
Molecular Formula
Synonyms
- Euscaphic acid
- 53155-25-2
- Acuminatic acid
- Jacarandic acid
- CHEBI:67914
Molecular Weight
488.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-08-01
- Modify:2025-01-18
Description
Euscaphic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 19 respectively (the 2alpha,3alpha-stereoisomer). It has been isolated from the leaves of Rosa laevigata. It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a hydroxy monocarboxylic acid and a triol. It derives from a hydride of an ursane.
Euscaphic acid has been reported in Rosa woodsii, Cotoneaster simonsii, and other organisms with data available.
Chemical Structure Depiction
(1R,2R,4aS,6aR,6aS,6bR,8aR,10S,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23-,26+,27-,28-,29-,30+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
OXVUXGFZHDKYLS-QUFHAEKXSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(C[C@H]([C@H](C5(C)C)O)O)C)C)[C@@H]2[C@]1(C)O)C)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C30H48O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- (2alpha,3beta)-isomer of euscaphic acid
- 2alpha-acetyl tormentic acid
- euscaphic acid
- jacarandic acid
- Euscaphic acid
- 53155-25-2
- Acuminatic acid
- Jacarandic acid
- CHEBI:67914
- (1R,2R,4aS,6aR,6aS,6bR,8aR,10S,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
- NSC-733507
- 2alpha,3alpha,19alpha-Trihydroxyurs-12-en-28-oic acid
- (2alpha,3alpha)-2,3,19-trihydroxyurs-12-en-28-oic acid
- LG23EX5V2J
- Euscaphate
- Jacarandate
- Euscapic acid
- Euscophic acid
- NSC 733507
- SCHEMBL869457
- CHEMBL239075
- DTXSID201317438
- HY-N2566
- BDBM50543759
- NSC733507
- AKOS032948559
- (2alpha,3beta)-Isomer OF euscaphic acid
- DA-73263
- MS-29089
- CS-0022899
- C17890
- Q27136388
- 2 alpha,3 alpha,19 alpha-trihydroxyurs-12-en-28-oic acid
- Urs-12-en-28-oic acid,3,19-trihydroxy-, (2.alpha.,3alpha.)-
- Urs-12-en-28-oic acid, 2,3,19-trihydroxy-, (2.alpha.,3.alpha.)-
- (1S,2S,4AS,6AS,6AS,6BR,8AR,10S,11R,12AS,14BS)-1,2,6A,6B,9,9,12A-HEPTAMETHYL-1,10,11-TRIS(OXIDANYL)-2,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-TETRADECAHYDROPICENE-4A-CARBOXYLIC ACID
- 1,10,11-Trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
488.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
488.35017463 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
488.35017463 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
98 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
35
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
956
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
11
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)
Solid
270 - 271 °C
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
PubMed Count
- Extracellular
- Membrane
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=OXVUXGFZHDKYLS-QUFHAEKXSA-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/Euscaphic acidhttps://commonchemistry.cas.org/detail?cas_rn=53155-25-2
- DTP/NCILICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuse
- EPA DSSToxEuscaphic acidhttps://comptox.epa.gov/dashboard/DTXSID201317438CompTox 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
- Human Metabolome Database (HMDB)LICENSEHMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.http://www.hmdb.ca/citingEuscaphic acidhttp://www.hmdb.ca/metabolites/HMDB0036651
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Euscaphic acidhttps://www.wikidata.org/wiki/Q27136388LOTUS 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
- FooDBLICENSEFooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.https://foodb.ca/aboutEuscaphic acidhttps://foodb.ca/compounds/FDB015576
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- Natural Product Activity and Species Source (NPASS)
- Metabolomics Workbench
- SpectraBase2-ALPHA,3-ALPHA,19-ALPHA-TRIHYDROXY-URS-12-EN-28-OIC-ACIDhttps://spectrabase.com/spectrum/9936y3DXl0E2-ALPHA,3-ALPHA,19-ALPHA-TRIHYDROXY-URS-12-EN-28-OIC-ACIDhttps://spectrabase.com/spectrum/Kmf2aNxqTAz
- Springer Nature
- Wikidataeuscaphic acidhttps://www.wikidata.org/wiki/Q27136388
- 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.htmleuscaphic acidhttps://www.ncbi.nlm.nih.gov/mesh/67007695
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 394149794https://pubchem.ncbi.nlm.nih.gov/substance/394149794
CONTENTS