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Record Information
Version1.0
Created at2022-09-12 02:23:04 UTC
Updated at2022-09-12 02:23:05 UTC
NP-MRD IDNP0323145
Secondary Accession NumbersNone
Natural Product Identification
Common Namedehydroergosterol acetate
DescriptionDehydroergosterol acetate belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. dehydroergosterol acetate is found in Chlorella vulgaris. It was first documented in 2006 (PMID: 17018531). Based on a literature review a small amount of articles have been published on Dehydroergosterol acetate (PMID: 30092384) (PMID: 29516493).
Structure
Thumb
Synonyms
ValueSource
Dehydroergosterol acetic acidGenerator
Chemical FormulaC30H44O2
Average Mass436.6800 Da
Monoisotopic Mass436.33413 Da
IUPAC Name(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),7,9-trien-5-yl acetate
Traditional Name(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),7,9-trien-5-yl acetate
CAS Registry NumberNot Available
SMILES
CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@H](CC[C@]4(C)C3=CC[C@]12C)OC(C)=O
InChI Identifier
InChI=1S/C30H44O2/c1-19(2)20(3)8-9-21(4)26-12-13-27-25-11-10-23-18-24(32-22(5)31)14-16-29(23,6)28(25)15-17-30(26,27)7/h8-11,15,19-21,24,26-27H,12-14,16-18H2,1-7H3/b9-8+/t20-,21+,24-,26+,27-,29-,30+/m0/s1
InChI KeyUSXNJOVHHSKEBV-RDQHZIOXSA-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
Chlorella vulgarisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgostane steroids
Alternative Parents
Substituents
  • Ergostane-skeleton
  • Steroid ester
  • Delta-7-steroid
  • Delta-5-steroid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP6.67ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity137.13 m³·mol⁻¹ChemAxon
Polarizability54.92 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID32699745
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound69827569
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lee S, Choi E, Yang SM, Ryoo R, Moon E, Kim SH, Kim KH: Bioactive compounds from sclerotia extract of Poria cocos that control adipocyte and osteoblast differentiation. Bioorg Chem. 2018 Dec;81:27-34. doi: 10.1016/j.bioorg.2018.07.031. Epub 2018 Jul 31. [PubMed:30092384 ]
  2. Modzel M, Solanko KA, Szomek M, Hansen SK, Dupont A, Nabo LJ, Kongsted J, Wustner D: Live-cell imaging of new polyene sterols for improved analysis of intracellular cholesterol transport. J Microsc. 2018 Jul;271(1):36-48. doi: 10.1111/jmi.12691. Epub 2018 Mar 8. [PubMed:29516493 ]
  3. Liou HL, Dixit SS, Xu S, Tint GS, Stock AM, Lobel P: NPC2, the protein deficient in Niemann-Pick C2 disease, consists of multiple glycoforms that bind a variety of sterols. J Biol Chem. 2006 Dec 1;281(48):36710-23. doi: 10.1074/jbc.M608743200. Epub 2006 Oct 2. [PubMed:17018531 ]
  4. LOTUS database [Link]