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Record Information
Version2.0
Created at2022-09-11 05:15:34 UTC
Updated at2022-09-11 05:15:34 UTC
NP-MRD IDNP0310151
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,3r,6s,9s,10s,11s,13e,17r,19s,20r)-17-hydroxy-3,6,19-trimethyl-9-(prop-1-en-2-yl)-16-oxapentacyclo[12.5.1.0³,¹¹.0⁶,¹⁰.0¹⁷,²⁰]icos-13-en-15-one
DescriptionVariecolactone belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (1s,3r,6s,9s,10s,11s,13e,17r,19s,20r)-17-hydroxy-3,6,19-trimethyl-9-(prop-1-en-2-yl)-16-oxapentacyclo[12.5.1.0³,¹¹.0⁶,¹⁰.0¹⁷,²⁰]icos-13-en-15-one is found in Aspergillus aurantiobrunneus and Aspergillus purpureus. (1s,3r,6s,9s,10s,11s,13e,17r,19s,20r)-17-hydroxy-3,6,19-trimethyl-9-(prop-1-en-2-yl)-16-oxapentacyclo[12.5.1.0³,¹¹.0⁶,¹⁰.0¹⁷,²⁰]icos-13-en-15-one was first documented in 2006 (PMID: 16462061). Based on a literature review very few articles have been published on Variecolactone (PMID: 29248948).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H36O3
Average Mass384.5600 Da
Monoisotopic Mass384.26645 Da
IUPAC Name(1S,3R,6S,9S,10S,11S,17R,19S,20R)-17-hydroxy-3,6,19-trimethyl-9-(prop-1-en-2-yl)-16-oxapentacyclo[12.5.1.0^{3,11}.0^{6,10}.0^{17,20}]icos-13-en-15-one
Traditional Name(1S,3R,6S,9S,10S,11S,17R,19S,20R)-17-hydroxy-3,6,19-trimethyl-9-(prop-1-en-2-yl)-16-oxapentacyclo[12.5.1.0^{3,11}.0^{6,10}.0^{17,20}]icos-13-en-15-one
CAS Registry NumberNot Available
SMILES
C[C@H]1C[C@@]2(O)OC(=O)\C3=C\C[C@H]4[C@@H]5[C@H](CC[C@@]5(C)CC[C@]4(C)C[C@@H]1[C@@H]23)C(C)=C
InChI Identifier
InChI=1S/C25H36O3/c1-14(2)16-8-9-23(4)10-11-24(5)13-18-15(3)12-25(27)20(18)17(22(26)28-25)6-7-19(24)21(16)23/h6,15-16,18-21,27H,1,7-13H2,2-5H3/b17-6+/t15-,16+,18-,19-,20-,21-,23-,24+,25+/m0/s1
InChI KeyFHJWMBGJDFBYNQ-SSPKKXFYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Emericella aurantiobrunneaLOTUS Database
Emericella purpureaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Hemiacetal
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.35ChemAxon
pKa (Strongest Acidic)11.58ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity110.92 m³·mol⁻¹ChemAxon
Polarizability44.34 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00032472
Chemspider ID8244156
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVariecolactone
METLIN IDNot Available
PubChem Compound10068616
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hosoe T, Itabashi T, Kobayashi N, Udagawa S, Kawai K: Three new types of indoloditerpenes, emindole PA-PC, from Emericella purpurea. Revision of the structure of emindole PA. Chem Pharm Bull (Tokyo). 2006 Feb;54(2):185-7. doi: 10.1248/cpb.54.185. [PubMed:16462061 ]
  2. Yodsing N, Lekphrom R, Sangsopha W, Aimi T, Boonlue S: Secondary Metabolites and Their Biological Activity from Aspergillus aculeatus KKU-CT2. Curr Microbiol. 2018 May;75(5):513-518. doi: 10.1007/s00284-017-1411-y. Epub 2017 Dec 16. [PubMed:29248948 ]
  3. LOTUS database [Link]