Np mrd loader

Record Information
Version1.0
Created at2022-02-14 20:48:31 UTC
Updated at2022-03-10 22:17:42 UTC
NP-MRD IDNP0044315
Secondary Accession NumbersNone
Natural Product Identification
Common Name5alpha-Campestan-3-one
Description5Alpha-campestan-3-one, also known as 3-dehydro-campestanol or methylcholestanone, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 5alpha-campestan-3-one is considered to be a sterol lipid molecule. 5Alpha-campestan-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5Alpha-Campestan-3-one is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
(24R)-24-Methyl-5alpha-cholestan-3-oneChEBI
(24R)-5alpha-Ergostan-3-oneChEBI
3-Dehydro-campestanolChEBI
Campestan-3-oneChEBI
MethylcholestanoneChEBI
(24R)-24-Methyl-5a-cholestan-3-oneGenerator
(24R)-24-Methyl-5α-cholestan-3-oneGenerator
(24R)-5a-Ergostan-3-oneGenerator
(24R)-5Α-ergostan-3-oneGenerator
5a-Campestan-3-oneGenerator
5Α-campestan-3-oneGenerator
(5alpha)-Campestan-3-oneHMDB
(5alpha,24R)-Ergostan-3-oneHMDB
(5α)-Campestan-3-oneHMDB
(5α,24R)-Ergostan-3-oneHMDB
5alpha-Campestan-3-oneHMDB
OstreastanoneHMDB
Chemical FormulaC28H48O
Average Mass400.6910 Da
Monoisotopic Mass400.37052 Da
IUPAC Name(1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
Traditional Name(1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
CAS Registry Number27212-88-0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C
InChI Identifier
InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-21,23-26H,7-17H2,1-6H3/t19-,20-,21+,23+,24-,25+,26+,27+,28-/m1/s1
InChI KeyDDJMOMHMVFXEQF-JBQSTXLYSA-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP6.41ALOGPS
logP8.01ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.29 m³·mol⁻¹ChemAxon
Polarizability52.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012116
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028780
KNApSAcK IDNot Available
Chemspider ID17221007
KEGG Compound IDC15786
BioCyc IDCPD-709
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061343
PDB IDNot Available
ChEBI ID18533
Good Scents IDNot Available
References
General References
  1. Kyselka J, Honzikova T, Vachalova T, Jiraskova T, Alishevich K, Rottnerova Z, Brychova V, Bercikova M, Hradkova I, Filip V: Formation of 5alpha-Sitostan-3-one, 5alpha-Campestan-3-one, and Steroidal Hydrocarbons in Edible Oils during Catalytic Hydrogenation. J Agric Food Chem. 2019 Sep 4;67(35):9916-9925. doi: 10.1021/acs.jafc.9b03054. Epub 2019 Aug 22. [PubMed:31398025 ]
  2. Nomura T, Jager CE, Kitasaka Y, Takeuchi K, Fukami M, Yoneyama K, Matsushita Y, Nyunoya H, Takatsuto S, Fujioka S, Smith JJ, Kerckhoffs LH, Reid JB, Yokota T: Brassinosteroid deficiency due to truncated steroid 5alpha-reductase causes dwarfism in the lk mutant of pea. Plant Physiol. 2004 Aug;135(4):2220-9. doi: 10.1104/pp.104.043786. Epub 2004 Jul 30. [PubMed:15286289 ]