Basic information
- CAS
21651-53-6- Standard SMILES
CC1=COC(=O)[C@H]2[C@@H](C)CC[C@@H]12- InChIKey
ZDKZHVNKFOXMND-XVYDVKMFSA-N- Molecular formula
- C10H14O2
- Average molar mass
- 166.22 g/mol
- Monoisotopic mass
- 166.09937969
Overview
Cis-cis-nepetalactone is a cyclopentapyran that is (4aR,7aS)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aR,7S,7aS-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It has a role as a plant metabolite. It is a cyclopentapyran and an iridoid monoterpenoid.
Names & identifiers
- Preferred name
- 4abeta,7alpha,7abeta-Nepetalactone
- IUPAC
- (4aR,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
Names & synonyms
(4aR,7S,7aS)-Nepetalactone21651-53-64abeta,7alpha,7abeta-NepetalactoneL488Q0FFC1Nepetalactone, (+)-(4aR,7S,7aS)-DTXSID1075197RefChem:1071746DTXCID2036530cis,cis-Nepetalactone(+)-cis,cis-Nepetalactonecis-cis-nepetalactoneNepetalactone, cis,cis
Show more names
UNII-L488Q0FFC1(+)-(4aR,7S,7aS)-nepetalactone(4aR,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-oneCyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aR,7S,7aS)-Cyclopenta[c]pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aR,7S,7aS)-4a.beta.,7.alpha.,7a.beta.-Nepetalactone(4aR,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-oneZ,Z-NEPETALACTONE
Database identifiers
- CAS
21651-53-6- PubChem CID
- 6431022
- DTXSID
DTXSID1075197- ChEBI
CHEBI:144482- UNII
- L488Q0FFC1
- Nikkaji
- J9.382C
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 242
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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