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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:06 UTC
HMDB IDHMDB0000878
Secondary Accession Numbers
  • HMDB00878
Metabolite Identification
Common NameErgosterol
DescriptionErgosterol, also known as provitamin D2, 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, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes.
Structure
Thumb
Synonyms
Chemical FormulaC28H44O
Average Molecular Weight396.659
Monoisotopic Molecular Weight396.339216037
IUPAC Name(1S,2R,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-7,9-dien-5-ol
Traditional Name(1S,2R,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-7,9-dien-5-ol
CAS Registry Number57-87-4
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C
InChI Identifier
InChI=1S/C28H44O/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/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
InChI KeyDNVPQKQSNYMLRS-APGDWVJJSA-N
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-hydroxy-delta-5-steroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling Point501.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility16 mg/mLNot Available
LogP9.300 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.009326 (0.003782-0.014870) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04038
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00023755
Chemspider ID392539
KEGG Compound IDC01694
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkErgosterol
METLIN IDNot Available
PubChem Compound444679
PDB IDNot Available
ChEBI ID16933
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1242781
References
Synthesis ReferenceHe, Xiuping; Zhang, Borun; Tan, Huarong. Overexpression of a sterol C-24(28) reductase increases ergosterol production in Saccharomyces cerevisiae. Biotechnology Letters (2003), 25(10), 773-778.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [PubMed:1287164 ]
  2. Liu TT, Lee RE, Barker KS, Lee RE, Wei L, Homayouni R, Rogers PD: Genome-wide expression profiling of the response to azole, polyene, echinocandin, and pyrimidine antifungal agents in Candida albicans. Antimicrob Agents Chemother. 2005 Jun;49(6):2226-36. [PubMed:15917516 ]
  3. Ferreira ME, Colombo AL, Paulsen I, Ren Q, Wortman J, Huang J, Goldman MH, Goldman GH: The ergosterol biosynthesis pathway, transporter genes, and azole resistance in Aspergillus fumigatus. Med Mycol. 2005 May;43 Suppl 1:S313-9. [PubMed:16110826 ]
  4. Akins RA: An update on antifungal targets and mechanisms of resistance in Candida albicans. Med Mycol. 2005 Jun;43(4):285-318. [PubMed:16110776 ]
  5. Matsumori N, Sawada Y, Murata M: Mycosamine orientation of amphotericin B controlling interaction with ergosterol: sterol-dependent activity of conformation-restricted derivatives with an amino-carbonyl bridge. J Am Chem Soc. 2005 Aug 3;127(30):10667-75. [PubMed:16045354 ]
  6. Kim DH, Jung SJ, Chung IS, Lee YH, Kim DK, Kim SH, Kwon BM, Jeong TS, Park MH, Seoung NS, Baek NI: Ergosterol peroxide from flowers of Erigeron annuus L. as an anti-atherosclerosis agent. Arch Pharm Res. 2005 May;28(5):541-5. [PubMed:15974439 ]