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Record Information
Version2.0
Created at2022-04-28 10:05:09 UTC
Updated at2022-04-28 10:05:09 UTC
NP-MRD IDNP0065896
Secondary Accession NumbersNone
Natural Product Identification
Common NamePeridininol
DescriptionPeridininol belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Peridininol is found in Amphidinium carterae, Anemonia sulcata, Corbicula japonica , Magallana gigas, Mytilus unguiculatus and Thoracosphaera heimii. Peridininol was first documented in 2005 (PMID: 16218688). Based on a literature review a small amount of articles have been published on Peridininol (PMID: 19053385) (PMID: 18952044).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC37H48O6
Average Mass588.7850 Da
Monoisotopic Mass588.34509 Da
IUPAC Name(5Z)-5-[(2E,4E,6E,8E)-11-[(2R,4S)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-2,9-dimethylundeca-2,4,6,8,10-pentaen-1-ylidene]-3-[(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]-2,5-dihydrofuran-2-one
Traditional Name(5Z)-5-[(2E,4E,6E,8E)-11-[(2R,4S)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-2,9-dimethylundeca-2,4,6,8,10-pentaen-1-ylidene]-3-[(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]furan-2-one
CAS Registry NumberNot Available
SMILES
C\C(=C/C=C/C=C/C=C(\C)/C=C1\OC(=O)C(\C=C\[C@@]23O[C@]2(C)C[C@@H](O)CC3(C)C)=C1)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O
InChI Identifier
InChI=1S/C37H48O6/c1-25(15-16-31-33(3,4)21-28(38)23-35(31,7)41)13-11-9-10-12-14-26(2)19-30-20-27(32(40)42-30)17-18-37-34(5,6)22-29(39)24-36(37,8)43-37/h9-15,17-20,28-29,38-39,41H,21-24H2,1-8H3/b11-9+,12-10+,18-17+,25-13+,26-14+,30-19-/t16?,28-,29-,35+,36+,37-/m0/s1
InChI KeyGWNBJBMUGIZCIP-VWLXYMLYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Amphidinium carteraeProtozoa
Anemonia sulcataAnimalia
Corbicula japonicaPlant
Magallana gigasLOTUS Database
Mytilus unguiculatusLOTUS Database
Thoracosphaera heimiiLOTUS 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
  • Cyclofarsesane sesquiterpenoid
  • Sesquiterpenoid
  • Oxepane
  • 2-furanone
  • Cyclic alcohol
  • Dihydrofuran
  • Enol ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxacycle
  • Organoheterocyclic compound
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • 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
logP6.71ALOGPS
logP4.81ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)14.01ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity179.55 m³·mol⁻¹ChemAxon
Polarizability69.79 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00023163
Chemspider ID59700174
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101764618
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Maoka T, Fujiwara Y, Hashimoto K, Akimoto N: Carotenoids in three species of Corbicula Clams, Corbicula japonica, Corbicula sandai, and Corbicula sp. (Chinese Freshwater Corbicula Clam). J Agric Food Chem. 2005 Oct 19;53(21):8357-64. doi: 10.1021/jf058088t. [PubMed:16218688 ]
  2. Maoka T, Akimoto N, Yim MJ, Hosokawa M, Miyashita K: New C37 skeletal carotenoid from the clam, Paphia amabillis. J Agric Food Chem. 2008 Dec 24;56(24):12069-72. doi: 10.1021/jf802717b. [PubMed:19053385 ]
  3. Sugawara T, Yamashita K, Asai A, Nagao A, Shiraishi T, Imai I, Hirata T: Esterification of xanthophylls by human intestinal Caco-2 cells. Arch Biochem Biophys. 2009 Mar 15;483(2):205-12. doi: 10.1016/j.abb.2008.10.007. Epub 2008 Oct 12. [PubMed:18952044 ]