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Record Information
Version2.0
Created at2022-09-12 01:36:03 UTC
Updated at2022-09-12 01:36:03 UTC
NP-MRD IDNP0322683
Secondary Accession NumbersNone
Natural Product Identification
Common Namecalaxin
DescriptionCalaxin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. calaxin is found in Heliomeris obscura, Sclerocarpus sessilifolius and Dendroviguiera eriophora. calaxin was first documented in 2017 (PMID: 28883641). Based on a literature review a small amount of articles have been published on Calaxin (PMID: 33845135) (PMID: 31286071) (PMID: 31240264) (PMID: 29386625).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H20O6
Average Mass344.3630 Da
Monoisotopic Mass344.12599 Da
IUPAC Name(2Z,4R,8R,9R,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate
Traditional Name(2Z,4R,8R,9R,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate
CAS Registry NumberNot Available
SMILES
CC(=C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12
InChI Identifier
InChI=1S/C19H20O6/c1-9(2)17(21)24-14-8-19(5)15(20)7-12(25-19)10(3)6-13-16(14)11(4)18(22)23-13/h6-7,13-14,16H,1,4,8H2,2-3,5H3/b10-6-/t13-,14-,16+,19-/m1/s1
InChI KeyRYBHZNMPMHOBAR-IRNKKCRZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Heliomeris obscuraLOTUS Database
Sclerocarpus sessilifoliusLOTUS Database
Viguiera eriophoraLOTUS 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
  • Dicarboxylic acid or derivatives
  • 3-furanone
  • Gamma butyrolactone
  • Dihydrofuran
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP2.68ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.55 m³·mol⁻¹ChemAxon
Polarizability34.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003227
Chemspider ID4444778
KEGG Compound IDC09353
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281431
PDB IDNot Available
ChEBI ID3302
Good Scents IDNot Available
References
General References
  1. Huan P, Cui M, Wang Q, Liu B: CRISPR/Cas9-mediated mutagenesis reveals the roles of calaxin in gastropod larval cilia. Gene. 2021 Jun 30;787:145640. doi: 10.1016/j.gene.2021.145640. Epub 2021 Apr 21. [PubMed:33845135 ]
  2. Sasaki K, Shiba K, Nakamura A, Kawano N, Satouh Y, Yamaguchi H, Morikawa M, Shibata D, Yanase R, Jokura K, Nomura M, Miyado M, Takada S, Ueno H, Nonaka S, Baba T, Ikawa M, Kikkawa M, Miyado K, Inaba K: Erratum: Publisher Correction: Calaxin is required for cilia-driven determination of vertebrate laterality. Commun Biol. 2019 Jul 4;2:254. doi: 10.1038/s42003-019-0512-5. eCollection 2019. [PubMed:31286071 ]
  3. Sasaki K, Shiba K, Nakamura A, Kawano N, Satouh Y, Yamaguchi H, Morikawa M, Shibata D, Yanase R, Jokura K, Nomura M, Miyado M, Takada S, Ueno H, Nonaka S, Baba T, Ikawa M, Kikkawa M, Miyado K, Inaba K: Calaxin is required for cilia-driven determination of vertebrate laterality. Commun Biol. 2019 Jun 20;2:226. doi: 10.1038/s42003-019-0462-y. eCollection 2019. [PubMed:31240264 ]
  4. Shojima T, Hou F, Takahashi Y, Matsumura Y, Okai M, Nakamura A, Mizuno K, Inaba K, Kojima M, Miyakawa T, Tanokura M: Crystal structure of a Ca(2+)-dependent regulator of flagellar motility reveals the open-closed structural transition. Sci Rep. 2018 Jan 31;8(1):2014. doi: 10.1038/s41598-018-19898-7. [PubMed:29386625 ]
  5. Mizuno K, Shiba K, Yaguchi J, Shibata D, Yaguchi S, Pruliere G, Chenevert J, Inaba K: Calaxin establishes basal body orientation and coordinates movement of monocilia in sea urchin embryos. Sci Rep. 2017 Sep 7;7(1):10751. doi: 10.1038/s41598-017-10822-z. [PubMed:28883641 ]
  6. LOTUS database [Link]