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Record Information
Version2.0
Created at2021-01-05 23:23:06 UTC
Updated at2021-07-15 17:16:28 UTC
NP-MRD IDNP0014133
Secondary Accession NumbersNone
Natural Product Identification
Common Name5α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl ester
Provided ByNPAtlasNPAtlas Logo
Description 5α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl ester is found in Laetiporus sulphureus and Laetiporus sulphureus var. miniatus. 5α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl ester was first documented in 2015 (PMID: 25916960). Based on a literature review very few articles have been published on 5alpha-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl ester.
Structure
Thumb
Synonyms
ValueSource
5a-Hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioate 3-methyl esterGenerator
5a-Hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl esterGenerator
5alpha-Hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioate 3-methyl esterGenerator
5Α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioate 3-methyl esterGenerator
5Α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl esterGenerator
(2R)-2-[(1S,3R,3AR,6S,7S,9BR)-1-hydroxy-6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,3ah,4H,5H,6H,7H,8H,9H,9BH-cyclopenta[a]naphthalen-3-yl]-6-methylhept-5-enoateGenerator
Chemical FormulaC31H48O5
Average Mass500.7200 Da
Monoisotopic Mass500.35017 Da
IUPAC Name(2R)-2-[(1S,3R,3aR,6S,7S,9bR)-1-hydroxy-6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,9bH-cyclopenta[a]naphthalen-3-yl]-6-methylhept-5-enoic acid
Traditional Name(2R)-2-[(1S,3R,3aR,6S,7S,9bR)-1-hydroxy-6-(3-methoxy-3-oxopropyl)-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,4H,5H,7H,8H,9H-cyclopenta[a]naphthalen-3-yl]-6-methylhept-5-enoic acid
CAS Registry NumberNot Available
SMILES
COC(=O)CC[C@@]1(C)[C@@H](CCC2=C1CC[C@]1(C)[C@H](C[C@H](O)[C@@]21C)[C@@H](CCC=C(C)C)C(O)=O)C(C)=C
InChI Identifier
InChI=1S/C31H48O5/c1-19(2)10-9-11-21(28(34)35)25-18-26(32)31(7)24-13-12-22(20(3)4)29(5,16-15-27(33)36-8)23(24)14-17-30(25,31)6/h10,21-22,25-26,32H,3,9,11-18H2,1-2,4-8H3,(H,34,35)/t21-,22+,25-,26+,29+,30-,31-/m1/s1
InChI KeyVSJFQUBIVAVZFS-GQRJWNNGSA-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
Laetiporus sulphureusLOTUS Database
Laetiporus sulphureus var. miniatusNPAtlas
Chemical Taxonomy
ClassificationNot classified
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
logP5.86ALOGPS
logP5.73ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.78ChemAxon
pKa (Strongest Basic)-0.44ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity144.38 m³·mol⁻¹ChemAxon
Polarizability59.53 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA000841
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78440718
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583322
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yin X, Li ZH, Li Y, Feng T, Liu JK: Four lanostane-type triterpenes from the fruiting bodies of mushroom Laetiporus sulphureus var. miniatus. J Asian Nat Prod Res. 2015;17(8):793-9. doi: 10.1080/10286020.2015.1027694. Epub 2015 Apr 28. [PubMed:25916960 ]