Showing metabocard for Vitamin A (BMDB0000305)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:28:08 UTC
Update Date2020-06-04 20:56:12 UTC
MCDB ID BMDB0000305
Secondary Accession Numbers
  • BMDB00305
Metabolite Identification
Common NameVitamin A
DescriptionVitamin a, also known as (13cis)-retinol, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Thus, vitamin a is considered to be an isoprenoid lipid molecule. Vitamin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Vitamin a exists in all living organisms, ranging from bacteria to humans. Vitamin a participates in a number of enzymatic reactions, within cattle. In particular, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme diacylglycerol O-acyltransferase 1. In addition, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme acyl-CoA wax alcohol acyltransferase 1. In cattle, vitamin a is involved in the metabolic pathway called the retinol metabolism pathway. Vitamin a is a potentially toxic compound. Vitamin a has been found to be associated with several diseases known as pregnancy, hemodialysis, and thyroid cancer; also vitamin a has been linked to the inborn metabolic disorders including abetalipoproteinemia.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-olChEBI
all-trans-Retinyl alcoholChEBI
all-trans-Vitamin a alcoholChEBI
AlphalinChEBI
Chocola aChEBI
RetinolChEBI
Vitamin a1ChEBI
Aquasol aKegg
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-olHMDB
all-trans-RetinolHMDB
b-RetinolHMDB
beta-RetinolHMDB
trans-RetinolHMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomerHMDB
all trans RetinolHMDB
11-cis-RetinolHMDB
Vitamin aChEBI
Chemical FormulaC20H30O
Average Molecular Weight286.4516
Monoisotopic Molecular Weight286.229665582
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
Traditional Nameα-sol
CAS Registry Number68-26-8
SMILES
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChI KeyFPIPGXGPPPQFEQ-OVSJKPMPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoid skeleton
  • Diterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61 - 63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP5.68BIOBYTE (1995)
Predicted Properties
PropertyValueSource
logP6.38ALOGPS
logP4.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.92 m³·mol⁻¹ChemAxon
Polarizability36.54 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1190000000-7c2230ee88e04e8f37412017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-7139000000-7242603c3f7f12c824cd2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0290000000-25c523b646154b291da82012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05gj-3900000000-a63c286f931608f650a32012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9700000000-e627db30469c74bb037f2012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0490000000-97ed49d705440e4d32e72017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ks-3930000000-7c5bfbd8b838b97dc2aa2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fri-9820000000-6a49bab0c891ffe1e5b22017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-d0ff1cdc72141d0daa0e2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-c0a067ff8ed271b809452017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-4590000000-cfc35aba420e707075f72017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-fe93459d3069e264b77f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mx-0190000000-f81760535f6050971f922021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00li-0960000000-4dbc516b202b90a6c2652021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-1890000000-fb68e645ac6c84dc722c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a9-2910000000-aa07b89a9cfe132b87252021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dl-5900000000-6de72efc591b252620c92021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-052r-2950000000-c24ec8ff8d0ba6c1f23f2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-18View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.653 - 2.308 uM details
Detected and Quantified0.566 uM details
Detected and Quantified1 +/- 0.04 uM
  • International Dai...
 details
Detected and Quantified1.1 +/- 0.3 uM
  • International Dai...
 details
Detected and Quantified0.1 +/- 0.04 uM
  • International Dai...
 details
Detected and Quantified0.0524 uM details
Detected and Quantified0.0733 uM details
Detected and Quantified0.0733 uM details
Detected and Quantified4.797 uM details
Detected and Quantified2.126 uM details
Detected and Quantified2.053 uM details
Detected and Quantified2.126 uM details
Detected and Quantified2.241 uM details
Detected and Quantified2.136 uM details
Detected and Quantified1.99 uM details
Detected and Quantified0.492 uM details
Detected and Quantified1.099 uM details
Detected and Quantified2.136 uM details
Detected and Quantified0.157 uM details
Detected and Quantified0.471 uM details
Detected and Quantified0.663 uM details
Detected and Quantified1.445 uM details
Detected and Quantified2.136 uM details
Detected and Quantified0.785 uM details
Detected and Quantified1.068 uM details
Detected and Quantified0.105 uM details
Detected and Quantified0.147 uM details
Detected and Quantified0.105 uM details
Detected and Quantified1.697 uM details
Detected and Quantified1.697 uM details
Detected and Quantified1.082 uM details
Detected and Quantified1.061 uM details
Detected and Quantified1.187 uM details
Detected and Quantified126 IU/100 g
  • Park, Y. W; Juáre...
 details
Detected and Quantified0.586 - 59 uM
  • Chotyakul N, Pate...
 details
Detected and Quantified0.349 - 3.491 uM
  • Oste R, Jagerstad...
 details
Detected and Quantified1.3195 uM
  • Park, Y. W; Juáre...
 details
Detected and Quantified0.052 - 4.797 uM details
Detected and Quantified0.65 +/- 0.02 uM details
Detected and Quantified0.70 +/- 0.01 uM details
Detected and Quantified0.55 +/- 0.01 uM details
Detected and Quantified0.265 +/- 0.004 uM details
HMDB IDHMDB0000305
DrugBank IDDB00162
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023841
KNApSAcK IDC00031437
Chemspider IDNot Available
KEGG Compound IDC17276
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVitamin_A
METLIN IDNot Available
PubChem Compound445354
PDB IDNot Available
ChEBI ID17336
References
Synthesis ReferenceIsler, O.; Ronco, A.; Guex, W.; Hindley, N. C.; Huber, W.; Dialer, K.; Kofler, M. Esters and ethers of synthetic vitamin A. Helvetica Chimica Acta (1949), 32 489-505.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74. [PubMed:1333471 ]
  2. Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2. [PubMed:16772583 ]
  3. 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 ]
  4. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
  5. M.C. Herrero-Barbudo, F. Granado-Lorencio, I. Blanco-Navarro, B. Olmedilla-Alonso (2005). International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526. International Dairy Journal.
  6. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
  7. 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.
  8. Nattaporn Chotyakul, Miriam Pateiro-Moure, Jorge Alexandre Saraiva, J. Antonio Torres, Concepción Pérez-Lamela (2014). Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 . European Food Research and Technology.
  9. Oste R, Jagerstad M, Anderson I (1997). Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman & Hall, pp 347–402, 1997. Chapman & Hall.
  10. USDA Food Composition Databases [Link]
  11. Fooddata+, The Technical University of Denmark (DTU) [Link]