Milk Composition Database: Showing metabocard for Ergocalciferol (BMDB0000900)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:19 UTC

Update Date

2020-06-04 20:39:02 UTC

MCDB ID

BMDB0000900

Secondary Accession Numbers

BMDB00900

Metabolite Identification

Common Name

Ergocalciferol

Description

Ergocalciferol, also known as vitamin D2 or viosterol, belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Thus, ergocalciferol is considered to be a secosteroid lipid molecule. Ergocalciferol is a drug which is used for use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin d resistant rickets). this drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin d dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with fanconi syndrome (with treatment of acidosis). Ergocalciferol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Ergocalciferol is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(3beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol	ChEBI
(5Z,7E,22E)-(3S)-9,10-Seco-5,7,10(19),22-ergostatetraen-3-ol	ChEBI
(5Z,7E,22E)-(3S)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol	ChEBI
Activated ergosterol	ChEBI
Calciferol	ChEBI
Ercalciol	ChEBI
Ergocalciferolum	ChEBI
Oleovitamin D2	ChEBI
Viosterol	ChEBI
Vitamina D2	ChEBI
Vitamin D2	Kegg
Drisdol	Kegg
(3b,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol	Generator
(3Β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol	Generator
(+)-Vitamin D2	HMDB
(5E,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraen-3-ol	HMDB
22-Tetraen 3beta 9,10,secoergosta-5,7,10(19)-ol	HMDB
4-Methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3ah)-indanylidene]ethylidene]-cyclohexanol	HMDB
9,10-Secoergosta-5,7,10(19),22-tetraen-3b-ol	HMDB
beta-Ol	HMDB
Buco-D	HMDB
Calciferon 2	HMDB
Condacaps	HMDB
Condocaps	HMDB
Condol	HMDB
Crtron	HMDB
Crystallina	HMDB
D-Arthin	HMDB
D-Tracetten	HMDB
Daral	HMDB
Davitamon D	HMDB
Davitin	HMDB
De-rat concentrate	HMDB
Decaps	HMDB
Dee-osterol	HMDB
Dee-ron	HMDB
Dee-ronal	HMDB
Dee-roual	HMDB
delta-Arthin	HMDB
delta-Tracetten	HMDB
Deltalin	HMDB
Deratol	HMDB
Detalup	HMDB
Diactol	HMDB
Divit urto	HMDB
Doral	HMDB
Ergocalciferol oil	HMDB
Ergorone	HMDB
Ergosterol activated	HMDB
Ergosterol irradiated	HMDB
Ertron	HMDB
Fortodyl	HMDB
Geltabs	HMDB
Hi-deratol	HMDB
Infron	HMDB
Irradiated ergosta-5,7,22-trien-3beta-ol	HMDB
Metadee	HMDB
Mina D2	HMDB
Mulsiferol	HMDB
Mykostin	HMDB
Novovitamin-D	HMDB
Oleovitamin D	HMDB
Osteil	HMDB
Ostelin	HMDB
Radiostol	HMDB
Radstein	HMDB
Radsterin	HMDB
Rodine C	HMDB
Shock-ferol	HMDB
Shock-ferol sterogyl	HMDB
Sterogyl	HMDB
Synthetic vitamin D	HMDB
Uvesterol D	HMDB
Uvesterol-D	HMDB
Vio D	HMDB
Vio-D	HMDB
Viostdrol	HMDB
Viosterol in oil	HMDB
Vitavel-D	HMDB
Calciferols	HMDB
Ergocalciferols	HMDB
D2, Vitamin	HMDB
Vitamin D 2	HMDB
Ergocalciferol	ChEBI

Chemical Formula

C₂₈H₄₄O

Average Molecular Weight

396.6484

Monoisotopic Molecular Weight

396.33921603

IUPAC Name

(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

Traditional Name

ergocalciferol

CAS Registry Number

50-14-6

SMILES

[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C

InChI Identifier

InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1

InChI Key

MECHNRXZTMCUDQ-RKHKHRCZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy seco-steroid (CHEBI:28934 )
seco-ergostane (CHEBI:28934 )
vitamin D (CHEBI:28934 )
Vitamin D2 and derivatives (C05441 )
Fat-soluble vitamins (C05441 )
Vitamin D2 and derivatives (LMST03010000 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	116.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.05 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.59	ALOGPS
logP	7.05	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.38	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.89 m³·mol⁻¹	ChemAxon
Polarizability	50.72 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-003u-3911000000-dba9e396497310b31715	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003u-3911000000-dba9e396497310b31715	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-3019000000-8a847f6179b3a364ad05	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0udl-4103900000-4c6f376ae6706d7e8556	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0129000000-77bd32807ec8ea97183b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0601-5902000000-ae4a4363ac10f9f0feb7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05mo-9800000000-1ea9f4fa17117a9e6515	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-01ot-9801000000-17d2120d47f9c718ea95	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01ot-9801000000-c10341d61ee2d6369219	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-1129000000-41a3f60b47798eb6bd6c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05ai-4694000000-95577608302dfef840b4	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gx9-9464000000-f7bcbdb6e805513cd661	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-819b52cfd84baf07f550	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-5ed8b1f535a88d73555c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3249000000-bf201c27d3bc67289adb	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006t-0398000000-dfcffd595ce9725ef52c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-4192000000-c93d9259f7db1789c50a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-015c-9340000000-aa858d8ca84ec1673a55	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-2f6aa9af0bd8878fb6c6	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0109000000-7977d6caa249a0925fb3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1759000000-2c5dd594802c53ac80a1	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.000504 uM	Pirjo H. Mattila,...	details
Detected and Quantified	0.00013 uM	Fooddata+, T...	details
Detected and Quantified	0.00013 uM	Fooddata+, T...	details
Detected and Quantified	0.00018 uM	Fooddata+, T...	details
Detected and Quantified	0.00192 uM	Fooddata+, T...	details
Detected and Quantified	0.00018 uM	Fooddata+, T...	details
Detected and Quantified	0.00252 uM	Fooddata+, T...	details
Detected and Quantified	0.00023 uM	Fooddata+, T...	details
Detected and Quantified	0.0002 uM	Fooddata+, T...	details
Detected and Quantified	0.0003 +/- 0.0001 uM	PMID: 30994344	details
Detected and Quantified	0.0003 +/- 0.0002 uM	PMID: 30994344	details
Detected and Quantified	0.0003 +/- 0.0001 uM	PMID: 30994344	details
Detected and Quantified	0.0003 +/- 0.0001 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000900

DrugBank ID

DB00153

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012811

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28934

References

Synthesis Reference

Okabe, Masami. Vitamin D2 from ergosterol (9,10-secoergosta-5,7,10(19),22-tetraen-3-ol,(3b)- from ergosta-5,7,22-trien-3-ol,(3b)-). Organic Syntheses (1999), 76 275-286.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen (1995). Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399. J. Agric. Food Chem.
Fooddata+, The Technical University of Denmark (DTU) [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Ergocalciferol (BMDB0000900)

Structure for BMDB0000900 (Ergocalciferol)