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Record Information
Version2.0
Created at2022-09-11 08:35:21 UTC
Updated at2022-09-11 08:35:21 UTC
NP-MRD IDNP0312098
Secondary Accession NumbersNone
Natural Product Identification
Common Namevariecolin
DescriptionVariecolin belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. variecolin is found in Aspergillus stellatus, Aspergillus aurantiobrunneus and Aspergillus purpureus. variecolin was first documented in 2004 (PMID: 15497939). Based on a literature review a small amount of articles have been published on Variecolin (PMID: 27806646) (PMID: 29298482) (PMID: 29248948) (PMID: 24096306).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H36O2
Average Mass368.5610 Da
Monoisotopic Mass368.27153 Da
IUPAC Name(1R,3S,4S,7R,8E,11S,12S,13S,16S)-1,4,16-trimethyl-6-oxo-13-(prop-1-en-2-yl)tetracyclo[9.7.0.0^{3,7}.0^{12,16}]octadec-8-ene-8-carbaldehyde
Traditional Name(1R,3S,4S,7R,8E,11S,12S,13S,16S)-1,4,16-trimethyl-6-oxo-13-(prop-1-en-2-yl)tetracyclo[9.7.0.0^{3,7}.0^{12,16}]octadec-8-ene-8-carbaldehyde
CAS Registry NumberNot Available
SMILES
C[C@H]1CC(=O)[C@@H]2[C@H]1C[C@@]1(C)CC[C@]3(C)CC[C@@H]([C@H]3[C@@H]1C\C=C2\C=O)C(C)=C
InChI Identifier
InChI=1S/C25H36O2/c1-15(2)18-8-9-24(4)10-11-25(5)13-19-16(3)12-21(27)22(19)17(14-26)6-7-20(25)23(18)24/h6,14,16,18-20,22-23H,1,7-13H2,2-5H3/b17-6-/t16-,18+,19-,20-,22-,23-,24-,25+/m0/s1
InChI KeyXAYQASOMEVLRKN-NOJNFTMQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus stellatusLOTUS Database
Emericella aurantiobrunneaLOTUS Database
Emericella purpureaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Variecolin sesterterpenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP5.22ChemAxon
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity110.93 m³·mol⁻¹ChemAxon
Polarizability43.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00033466
Chemspider ID4980914
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVariecolin
METLIN IDNot Available
PubChem Compound6480205
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yoganathan K, Rossant C, Glover RP, Cao S, Vittal JJ, Ng S, Huang Y, Buss AD, Butler MS: Inhibition of the human chemokine receptor CCR5 by variecolin and variecolol and isolation of four new variecolin analogues, emericolins A-D, from Emericella aurantiobrunnea. J Nat Prod. 2004 Oct;67(10):1681-4. doi: 10.1021/np049844c. [PubMed:15497939 ]
  2. Jouda JB, Fopossi JD, Kengne FM, Djama Mbazoa C, Golz C, Strohmann C, Fogue SK, Wandji J: Secondary metabolites from Aspergillus japonicus CAM231, an endophytic fungus associated with Garcinia preussii. Nat Prod Res. 2017 Apr;31(8):861-869. doi: 10.1080/14786419.2016.1250089. Epub 2016 Nov 3. [PubMed:27806646 ]
  3. Krout MR, Henry CE, Jensen T, Wu KL, Virgil SC, Stoltz BM: Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin. J Org Chem. 2018 Jul 6;83(13):6995-7009. doi: 10.1021/acs.joc.7b02972. Epub 2018 Jan 23. [PubMed:29298482 ]
  4. 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 ]
  5. Li K, Wang C, Yin G, Gao S: Construction of the basic skeleton of ophiobolin A and variecolin. Org Biomol Chem. 2013 Nov 21;11(43):7550-8. doi: 10.1039/c3ob41693c. [PubMed:24096306 ]
  6. LOTUS database [Link]