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Record Information
Version2.0
Created at2022-09-12 10:32:30 UTC
Updated at2022-09-12 10:32:30 UTC
NP-MRD IDNP0327712
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3s,4s)-2-[(3r,3as,4r,5s,7r,8ar)-3,4,7-trihydroxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-5-yl]-4-(acetyloxy)-6-methylhept-5-en-3-yl acetate
Description(2R,3S,4S)-2-[(3R,3aS,4R,5S,7R,8aR)-3,4,7-trihydroxy-3-methyl-8-methylidene-3,3a,4,5,6,7,8,8a-octahydroazulen-5-yl]-4-(acetyloxy)-6-methylhept-5-en-3-yl acetate belongs to the class of organic compounds known as pachydictyane and cneorubin diterpenoids. These are diterpenoids with a structure that is based either on the pachydictyane or the cneorubin skeleton. Pachydictyane is a bicyclic compound consisting of a guaiane skeleton that carries a prenyl group attached to the C12 carbon atom. Cneorubin is a tricyclic compound consisting of a cycloprop[e]azulene where the cyclopropane carries a methyl group and a 4-methylpentyl group. (2r,3s,4s)-2-[(3r,3as,4r,5s,7r,8ar)-3,4,7-trihydroxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-5-yl]-4-(acetyloxy)-6-methylhept-5-en-3-yl acetate is found in Dictyota dichotoma. Based on a literature review very few articles have been published on (2R,3S,4S)-2-[(3R,3aS,4R,5S,7R,8aR)-3,4,7-trihydroxy-3-methyl-8-methylidene-3,3a,4,5,6,7,8,8a-octahydroazulen-5-yl]-4-(acetyloxy)-6-methylhept-5-en-3-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(2R,3S,4S)-2-[(3R,3AS,4R,5S,7R,8ar)-3,4,7-trihydroxy-3-methyl-8-methylidene-3,3a,4,5,6,7,8,8a-octahydroazulen-5-yl]-4-(acetyloxy)-6-methylhept-5-en-3-yl acetic acidGenerator
Chemical FormulaC24H36O7
Average Mass436.5450 Da
Monoisotopic Mass436.24610 Da
IUPAC Name(2R,3S,4S)-2-[(3R,3aS,4R,5S,7R,8aR)-3,4,7-trihydroxy-3-methyl-8-methylidene-3,3a,4,5,6,7,8,8a-octahydroazulen-5-yl]-4-(acetyloxy)-6-methylhept-5-en-3-yl acetate
Traditional Name(2R,3S,4S)-2-[(3R,3aS,4R,5S,7R,8aR)-3,4,7-trihydroxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-5-yl]-4-(acetyloxy)-6-methylhept-5-en-3-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@@H]([C@H](OC(C)=O)[C@@H](OC(C)=O)C=C(C)C)[C@@H]1C[C@@H](O)C(=C)[C@@H]2C=C[C@@](C)(O)[C@@H]2[C@@H]1O
InChI Identifier
InChI=1S/C24H36O7/c1-12(2)10-20(30-15(5)25)23(31-16(6)26)14(4)18-11-19(27)13(3)17-8-9-24(7,29)21(17)22(18)28/h8-10,14,17-23,27-29H,3,11H2,1-2,4-7H3/t14-,17+,18+,19-,20+,21+,22-,23+,24-/m1/s1
InChI KeyLFAMFSQHBFIPSM-PRRJLTTFSA-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
Dictyota dichotomaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pachydictyane and cneorubin diterpenoids. These are diterpenoids with a structure that is based either on the pachydictyane or the cneorubin skeleton. Pachydictyane is a bicyclic compound consisting of a guaiane skeleton that carries a prenyl group attached to the C12 carbon atom. Cneorubin is a tricyclic compound consisting of a cycloprop[e]azulene where the cyclopropane carries a methyl group and a 4-methylpentyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentPachydictyane and cneorubin diterpenoids
Alternative Parents
Substituents
  • Pachydictyane or cneorubin diterpenoid
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP1.21ChemAxon
pKa (Strongest Acidic)13.99ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity117.24 m³·mol⁻¹ChemAxon
Polarizability47.06 ųChemAxon
Number of Rings2ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162996281
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]