Petasin
PubChem CID
5281526
Structure
Molecular Formula
Synonyms
- Petasin
- 26577-85-5
- (+)-Petasin
- UNII-9Z0Q32J0QC
- 9Z0Q32J0QC
Molecular Weight
316.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-06-24
- Modify:2025-01-25
Description
Petasin is an enoate ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of (1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-ol. It has a role as a plant metabolite, a vasodilator agent, an anti-allergic agent and an EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} activator. It is a sesquiterpenoid, an enone, an alicyclic ketone and an enoate ester. It is functionally related to an angelic acid.
Petasin has been reported in Tephroseris palustris, Sinacalia tangutica, and other organisms with data available.
Chemical Structure Depiction
[(1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-prop-1-en-2-yl-1,2,3,4,7,8-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3/b13-7-/t14-,16-,18+,20+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
ISTBXSFGFOYLTM-NZEDGPFZSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C/C=C(/C)\C(=O)O[C@@H]1CCC2=CC(=O)[C@@H](C[C@@]2([C@H]1C)C)C(=C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C20H28O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- (1R,2R,7R,8aR)-7-Isopropenyl-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-2-naphthalenyl (2Z)-2-methyl-2-butenoate
- (1R,2R,7S,8aR)-7-Isopropenyl-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-2-naphthalenyl (2Z)-3-(methylsulfanyl)acrylate
- neopetasin
- petasin
- S-petasin
- Petasin
- 26577-85-5
- (+)-Petasin
- UNII-9Z0Q32J0QC
- 9Z0Q32J0QC
- CHEBI:8030
- C09706
- [(1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-prop-1-en-2-yl-1,2,3,4,7,8-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
- 2-Butanoic acid, 2-methyl-, 1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenyl ester, (1R-(1alpha,2beta(Z),7beta,8aalpha))-
- 2-Butenoic acid, 2-methyl-, (1R,2R,7S,8aR)-1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenyl ester, (2Z)-
- AC1NQYL4
- PETAFORCE
- PETASINE
- O-Angeloylsencathenone
- SureCN12621121
- CHEMBL3291073
- SCHEMBL12621121
- DTXSID201030056
- ZINC05132525
- XP173205
- Q7171781
- (1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl (2Z)-2-methylbut-2-enoate
- [(1R,2R,7S,8aR)-7-isopropenyl-1,8a-dimethyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
- CROTONIC ACID, 2-METHYL-, ESTER WITH 3.ALPHA.-HYDROXY-EREMOPHILA-9,11-DIEN-8-ONE, (Z)-
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
316.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
316.20384475 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
316.20384475 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
43.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
596
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
1
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)
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
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
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- Japan Chemical Substance Dictionary (Nikkaji)
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- Natural Product Activity and Species Source (NPASS)
- Metabolomics Workbench
- SpectraBase#1;PETASIN;[1R-[1-ALPHA,2-ALPHA(Z),7-BETA,8A-ALPHA]-1,2,3,4,6,7,8,8A-OCTAHYDRO-1,8A-DIMETHYL-7-(1-METHYLETHENYL)-6-OXO-2-NAPHTHALENYL-2-METHYL-2-BUTENOIC-ACIDEhttps://spectrabase.com/spectrum/1zR9yOxKApx(+)-Petasinhttps://spectrabase.com/spectrum/G1NZ8nK0kEG
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- PubChem
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- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
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