MiMeDB: Showing metabocard for Ergosterol (MMDBc0000554)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:24 UTC

Update Date

2024-10-09 23:53:29 UTC

Metabolite ID

MMDBc0000554

Metabolite Identification

Common Name

Ergosterol

Description

Ergosterol, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(22E,24S)-24-Methylcholesta-5,7,22-trien-3beta-ol	ChEBI
Provitamin D2	ChEBI
(22E,24S)-24-Methylcholesta-5,7,22-trien-3b-ol	Generator
(22E,24S)-24-Methylcholesta-5,7,22-trien-3β-ol	Generator
Lumisterol	HMDB
Provitamin D 2	HMDB
D2, Pro-vitamin	HMDB
Pro vitamin D2	HMDB
Pro-vitamin D2	HMDB
(22E,24R)-Ergosta-5,7,22-trien-3beta-ol	HMDB
(22E,24R)-Ergosta-5,7,22-trien-3β-ol	HMDB
(24R)-Ergosta-5,7,22-trien-3beta-ol	HMDB
(24R)-Ergosta-5,7,22-trien-3β-ol	HMDB
(3beta,22E)-Ergosta-5,7,22-trien-3-ol	HMDB
(3Β,22E)-ergosta-5,7,22-trien-3-ol	HMDB
24-Methylcholesta-5,7,22-trien-3beta-ol	HMDB
24-Methylcholesta-5,7,22-trien-3β-ol	HMDB
24R-Methylcholesta-5,7,22E-trien-3beta-ol	HMDB
24R-Methylcholesta-5,7,22E-trien-3β-ol	HMDB
24alpha-Methyl-22E-dehydrocholesterol	HMDB
24Α-methyl-22E-dehydrocholesterol	HMDB
3beta-Hydroxyergosta-5,7,22-triene	HMDB
3Β-hydroxyergosta-5,7,22-triene	HMDB
Ergosterin	HMDB
Provitamin D	HMDB
Ergosterol	HMDB

Molecular Formula

C₂₈H₄₄O

Average Mass

396.659

Monoisotopic Mass

396.339216037

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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 Key

DNVPQKQSNYMLRS-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:16933 )
ergostanoid (CHEBI:16933 )
phytosterols (CHEBI:16933 )
Ergosterols and C24-methyl derivatives (C01694 )
Vitamin D2 and derivatives (C01694 )
Ergostane and derivatives (C01694 )
Ergosterols and C24-methyl derivatives (LMST01030093 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1		Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	6	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.009326	0.003782	0.014870	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	7499681
Human Blood	Detected and Quantified	0.009326	0.003782	0.014870	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	8791989
Human Blood	Detected and Quantified	0.009326	0.003782	0.014870	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	10705477
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000878

DrugBank ID

DB04038

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00023755

Chemspider ID

392539

KEGG Compound ID

C01694

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergosterol

METLIN ID

Not Available

PubChem Compound

444679

PDB ID

Not Available

ChEBI ID

16933

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. doi: 10.1080/02681219280000611. [PubMed:1287164 ]
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. doi: 10.1128/AAC.49.6.2226-2236.2005. [PubMed:15917516 ]
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. doi: 10.1007/BF02977755. [PubMed:15974439 ]
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. doi: 10.1021/ja051597r. [PubMed:16045354 ]
Akins RA: An update on antifungal targets and mechanisms of resistance in Candida albicans. Med Mycol. 2005 Jun;43(4):285-318. doi: 10.1080/13693780500138971. [PubMed:16110776 ]
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. doi: 10.1080/13693780400029114. [PubMed:16110826 ]

Showing metabocard for Ergosterol (MMDBc0000554)

MOL for #<Metabolite:0x00007fdb59a97540>

3D MOL for #<Metabolite:0x00007fdb59a97540>

3D SDF for #<Metabolite:0x00007fdb59a97540>

3D-SDF for #<Metabolite:0x00007fdb59a97540>

PDB for #<Metabolite:0x00007fdb59a97540>

3D PDB for #<Metabolite:0x00007fdb59a97540>

SMILES for #<Metabolite:0x00007fdb59a97540>

INCHI for #<Metabolite:0x00007fdb59a97540>

Structure for #<Metabolite:0x00007fdb59a97540>

3D Structure for #<Metabolite:0x00007fdb59a97540>