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Record Information
Version2.0
Created at2022-09-08 23:54:04 UTC
Updated at2022-09-08 23:54:04 UTC
NP-MRD IDNP0275978
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,4s,5r,8r,10s,13r,14r,16s,17s,18r)-16-bromo-10-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-23-one
Description3Beta,13beta-Dihydroxy-12alpha-bromo-5alpha-oleanane-28-oic acid 28,13-lactone, also known as 3β,13β-dihydroxy-12α-bromo-5α-oleanane-28-Oate 28,13-lactone, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,4s,5r,8r,10s,13r,14r,16s,17s,18r)-16-bromo-10-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosan-23-one is found in Nernstia mexicana. Based on a literature review very few articles have been published on 3beta,13beta-Dihydroxy-12alpha-bromo-5alpha-oleanane-28-oic acid 28,13-lactone.
Structure
Thumb
Synonyms
ValueSource
3b,13b-Dihydroxy-12a-bromo-5a-oleanane-28-Oate 28,13-lactoneGenerator
3b,13b-Dihydroxy-12a-bromo-5a-oleanane-28-Oic acid 28,13-lactoneGenerator
3beta,13beta-Dihydroxy-12alpha-bromo-5alpha-oleanane-28-Oate 28,13-lactoneGenerator
3Β,13β-dihydroxy-12α-bromo-5α-oleanane-28-Oate 28,13-lactoneGenerator
3Β,13β-dihydroxy-12α-bromo-5α-oleanane-28-Oic acid 28,13-lactoneGenerator
Chemical FormulaC30H47BrO3
Average Mass535.6070 Da
Monoisotopic Mass534.27086 Da
IUPAC Name(1S,4S,5R,8R,10S,13R,14R,16S,17S,18R)-16-bromo-10-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-23-one
Traditional Name(1S,4S,5R,8R,10S,13R,14R,16S,17S,18R)-16-bromo-10-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-23-one
CAS Registry NumberNot Available
SMILES
CC1(C)CC[C@@]23CC[C@]4(C)[C@@](OC2=O)([C@@H]3C1)[C@@H](Br)C[C@@H]1[C@@]2(C)CC[C@H](O)C(C)(C)[C@@H]2CC[C@@]41C
InChI Identifier
InChI=1S/C30H47BrO3/c1-24(2)12-14-29-15-13-28(7)27(6)11-8-18-25(3,4)22(32)9-10-26(18,5)19(27)16-21(31)30(28,20(29)17-24)34-23(29)33/h18-22,32H,8-17H2,1-7H3/t18-,19+,20+,21-,22-,26-,27+,28-,29-,30+/m0/s1
InChI KeyAKRMZTJSFJYCJR-NVTHVPAHSA-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
Nernstia mexicanaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Caprolactone
  • Oxepane
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Alkyl bromide
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Alkyl halide
  • Organohalogen compound
  • Organobromide
  • Organooxygen compound
  • 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
logP7.05ChemAxon
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity138.13 m³·mol⁻¹ChemAxon
Polarizability57.88 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
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 Compound13876967
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]