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Human Metabolome Database Version 3.5

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Showing metabocard for Brassicasterol (HMDB11181)

Record Information
Version 3.5
Creation Date 2008-10-30 07:54:46 -0600
Update Date 2013-02-08 17:25:51 -0700
HMDB ID HMDB11181
Secondary Accession Numbers None
Metabolite Identification
Common Name Brassicasterol
Description Brassicasterol is a 28 carbon sterol synthesised by several unicellular algae (phytoplankton) and some terrestrial plants (oilseed rape). This compound has frequently been used as a biomarker for the presence of (marine) algal matter in the environment.Wikipedia.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 24(R)-Methylcholesta-5,22E-dien-3beta-ol
  2. 24-Methylcholesta-5,22-dien-3beta-ol
  3. 5,22-Ergostadien-3beta-ol
  4. 5,22-Ergostadienol
  5. Brassicasterin
  6. Brassicasterol
  7. Ergosta-5,22(E)-dien-3beta-ol
  8. Ergosta-5,22-dien-3beta-ol
Chemical Formula C28H46O
Average Molecular Weight 398.6642
Monoisotopic Molecular Weight 398.354866094
IUPAC Name (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional IUPAC Name (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number 474-67-9
SMILES CC(C)[C@H](C)\C=C\[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
InChI Identifier InChI=1S/C28H46O/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/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1
InChI Key OILXMJHPFNGGTO-SDMVIZLASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Ergosterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Secondary Alcohol
Direct Parent Ergosterols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 150 - 151 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.470E-05 g/L ALOGPS
LogP 6.48 ALOGPS
LogP 7.04 ChemAxon
LogS -7.06 ALOGPS
pKa (strongest acidic) 18.2 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 126.28 ChemAxon
Polarizability 51.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.57 (0.25-1.8) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012496
KNApSAcK ID C00003646 Link_out
Chemspider ID 4446752 Link_out
KEGG Compound ID C08813 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Brassicasterol Link_out
NuGOwiki Link HMDB11181 Link_out
Metagene Link HMDB11181 Link_out
METLIN ID Not Available
PubChem Compound 5283660 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available