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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:51:18 UTC
HMDB IDHMDB0000878
Secondary Accession Numbers
  • HMDB00878
Metabolite Identification
Common NameErgosterol
DescriptionErgosterol, a sterol, 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
ValueSource
(22E)-Ergosta-5,7,22-trien-3-olHMDB
(24R)-Ergosta-5,7,22-trien-3b-olHMDB
(3beta)-Ergosta-5,7,22-trien-3-olHMDB
(3beta,22E)-Ergosta-5,7,22-trien-3-olHMDB
(3beta,2E)-Ergosta-5,7,22-trien-3-olHMDB
24-Methylcholesta-5,7,22-trien-3b-olHMDB
24-Methylcholesta-5,7,22-trien-3beta-olHMDB
24a-Methyl-22E-dehydrocholesterolHMDB
24alpha-Methyl-22E-dehydrocholesteroHMDB
24R-Methylcholesta-5,7,22E-trien-3b-olHMDB
24R-Methylcholesta-5,7,22E-trien-3beta-olHMDB
Ergosta-5,7,22-trien-3-olHMDB
ErgosterinHMDB
Provitamine D2HMDB
Chemical FormulaC28H44O
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
IUPAC Name(2R,5S,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional Name(2R,5S,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
CAS Registry Number57-87-4
SMILES
CC(C)[C@@H](C)\C=C\[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
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-KQYMERMZSA-N
Chemical Taxonomy
DescriptionThis compound 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 DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility16 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
logP7.39ALOGPS
logP6.63ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity127.13 m³·mol⁻¹ChemAxon
Polarizability49.94 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fsi-1019000000-1eb795b4071c3dc0a42cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udl-2003900000-c84feed3f7fbf11526ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0009000000-ca7841e724086fd88a01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05us-5891000000-5675b1af0ce9ff87b1a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-5920000000-6eca7b0791c4a09fb2e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1019000000-9682b479cb367468e4f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ss-6149000000-8fcdb7198ebd094e3658View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-9085000000-b5f06c3d8a32fea4fc08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-36b82459f90e5096bbffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-17e94d8c42f8b29d1d7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3019000000-d968e794cb4f844efc59View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.009326 (0.003782-0.014870) uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04038
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012612
KNApSAcK IDC00003652
Chemspider ID10477914
KEGG Compound IDC01694
BioCyc IDERGOSTEROL
BiGG IDNot Available
Wikipedia LinkErgosterol
METLIN ID5839
PubChem Compound21775588
PDB ID1BXM
ChEBI ID16933
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 ]