Milk Composition Database: Showing metabocard for Cholesterol (BMDB0000067)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:13 UTC

Update Date

2020-06-04 22:59:16 UTC

MCDB ID

BMDB0000067

Secondary Accession Numbers

BMDB00067

Metabolite Identification

Common Name

Cholesterol

Description

Cholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cholesterol is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta,14beta,17alpha)-Cholest-5-en-3-ol	ChEBI
Cholest-5-en-3beta-ol	ChEBI
Cholesterin	ChEBI
(3b,14b,17a)-Cholest-5-en-3-ol	Generator
(3Β,14β,17α)-cholest-5-en-3-ol	Generator
Cholest-5-en-3b-ol	Generator
Cholest-5-en-3β-ol	Generator
(3Β)-cholest-5-en-3-ol	HMDB
(3beta)-Cholest-5-en-3-ol	HMDB
3Β-hydroxycholest-5-ene	HMDB
3beta-Hydroxycholest-5-ene	HMDB
5:6-Cholesten-3β-ol	HMDB
5:6-Cholesten-3beta-ol	HMDB
(-)-Cholesterol	HMDB
Cholesterine	HMDB
Cholesterol base H	HMDB
Cholesteryl alcohol	HMDB
Cholestrin	HMDB
Cholestrol	HMDB
Cordulan	HMDB
Dastar	HMDB
Dusoline	HMDB
Dusoran	HMDB
Dythol	HMDB
Fancol CH	HMDB
Hydrocerin	HMDB
Kathro	HMDB
Lanol	HMDB
Super hartolan	HMDB
Tegolan	HMDB
Cholesterol	HMDB
delta5-Cholesten-3beta-ol	PhytoBank
Δ5-Cholesten-3β-ol	PhytoBank

Chemical Formula

C₂₇H₄₆O

Average Molecular Weight

386.6535

Monoisotopic Molecular Weight

386.354866094

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

57-88-5

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Cholesterol
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:16113 )
3beta-sterol (CHEBI:16113 )
cholestane (C00187 )
Cholesterol and derivatives (C00187 )
Cholestane and derivatives (C00187 )
Cholesterol and derivatives (LMST01010001 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.02	ALOGPS
logP	7.11	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	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	120.62 m³·mol⁻¹	ChemAxon
Polarizability	50.64 Å³	ChemAxon
Number of Rings	4	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)	splash10-004i-3911000000-52f5261007adc218f8f8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052b-2932000000-1667c83d002043a59fff	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000l-9527000000-5529a262047f5369c9c1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0mkr-2954000000-60e7d1f5973e4de33dec	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-1009000000-e82b8e23dedb45ce70e6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-056v-2900000000-04687c9f19ff52ba4654	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i3-1109000000-8cd386b595bd5151c5a2	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-3104900000-698223f49da0b0c1cf81	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 (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	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-052u-0690000000-36b4aea6637bdf069b5d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-014i-3639000000-18a9275beb9bae48c1d7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-014j-4934000000-f755ada933cfcf53c303	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0002-5921000000-e7d43c825b9f6d45e679	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0532-5910000000-ce90c49b7429a03a65da	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-05nb-8900000000-2e8913fec7126b5b2a62	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0apl-9600000000-3096c7a78c3dd2e6a538	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 50V, positive	splash10-067l-9400000000-1b57543b4cd0a05b9b3f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 60V, positive	splash10-0aru-9300000000-45a29b76dfefce3f01ca	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0009000000-dccd68f70545aeac4fab	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05p9-3149000000-7f25daf2b709c7e0d177	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c00-6269000000-5333d0216e01a3e43367	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-dc853b29b9e884bbb03b	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-09d9608700564a6fef78	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ldi-1009000000-96f6e67651380e1c959e	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-2d9cbc8b5b1fa392fb9b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abj-9173000000-9086873e4b65db1ced63	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8920000000-bd94fa538afb75d04765	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-c037f2d2f217e99b79ac	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-7de5154056e69e7319e1	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0009000000-96c53273291d4857bde4	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-7922000000-36e8a5e1a77d2e71d1d1	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-23	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	101 uM	PMID: 16859856	details
Detected and Quantified	362 uM	PMID: 11913692	details
Detected but not Quantified	Not Applicable	PMID: 1779072	details
Detected and Quantified	52 uM	USDA Food Co...	details
Detected and Quantified	52 uM	USDA Food Co...	details
Detected and Quantified	129 uM	USDA Food Co...	details
Detected and Quantified	52 uM	USDA Food Co...	details
Detected and Quantified	362 uM	USDA Food Co...	details
Detected and Quantified	103 uM	USDA Food Co...	details
Detected and Quantified	103 uM	USDA Food Co...	details
Detected and Quantified	129 uM	USDA Food Co...	details
Detected and Quantified	52 uM	USDA Food Co...	details
Detected and Quantified	52 uM	USDA Food Co...	details
Detected and Quantified	52 uM	USDA Food Co...	details
Detected and Quantified	52 uM	USDA Food Co...	details
Detected and Quantified	155 uM	Fooddata+, T...	details
Detected and Quantified	155 uM	Fooddata+, T...	details
Detected and Quantified	362 uM	USDA Food Co...	details
Detected and Quantified	206 uM	USDA Food Co...	details
Detected and Quantified	206 uM	USDA Food Co...	details
Detected and Quantified	206 uM	USDA Food Co...	details
Detected and Quantified	206 uM	USDA Food Co...	details
Detected and Quantified	206 uM	USDA Food Co...	details
Detected and Quantified	78 uM	Fooddata+, T...	details
Detected and Quantified	90 uM	Fooddata+, T...	details
Detected and Quantified	78 uM	Fooddata+, T...	details
Detected and Quantified	258 uM	USDA Food Co...	details
Detected and Quantified	258 uM	USDA Food Co...	details
Detected and Quantified	362 uM	Fooddata+, T...	details
Detected and Quantified	362 uM	Fooddata+, T...	details
Detected and Quantified	362 uM	Fooddata+, T...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details

External Links

HMDB ID

HMDB0000067

DrugBank ID

DB04540

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013269

KNApSAcK ID

C00003648

Chemspider ID

Not Available

KEGG Compound ID

C00187

BioCyc ID

CHOLESTEROL

BiGG ID

Not Available

Wikipedia Link

Cholesterol

METLIN ID

Not Available

PubChem Compound

5997

PDB ID

Not Available

ChEBI ID

16113

References

Synthesis Reference

Zhu, Yongming; Qin, Liena; Liu, Rui. Simple method for synthesis cholesterol from Diosgenin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Shi Y, Zhang JH, Shi D, Jiang M, Zhu YX, Mei SR, Zhou YK, Dai K, Lu B: Selective solid-phase extraction of cholesterol using molecularly imprinted polymers and its application in different biological samples. J Pharm Biomed Anal. 2006 Nov 16;42(5):549-55. doi: 10.1016/j.jpba.2006.05.022. Epub 2006 Jul 21. [PubMed:16859856 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
USDA Food Composition Databases [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Cholesterol (BMDB0000067)

Structure for BMDB0000067 (Cholesterol)