Milk Composition Database: Showing metabocard for Alpha-CEHC (BMDB0001518)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:06 UTC

Update Date

2020-04-22 15:08:32 UTC

MCDB ID

BMDB0001518

Secondary Accession Numbers

BMDB01518

Metabolite Identification

Common Name

Alpha-CEHC

Description

Alpha-Cehc, also known as Α-cehc, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Alpha-Cehc is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Alpha-Cehc exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
a-CEHC	Generator
Α-cehc	Generator
3-(6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoate	HMDB
α-Carboxyethyl hydrochroman	HMDB
alpha-Carboxyethyl hydrochroman	Generator
2,5,7,8-Tetramethyl-2(2'-carboxyethyl)-6-hydroxychroman	HMDB
2,5,7,8-Tetramethyl-2-(β-carboxyethyl)-6-hydroxychroman	Generator
2,5,7,8-Tetramethyl-2-(beta-carboxyethyl)-6-hydroxychroman	HMDB
6-Hydroxy-2-(2-carboxylethyl)-2,5,7,8-tetramethylchroman	HMDB
6-Hydroxy-2-carboxylethyl-2,5,7,8-tetramethylchroman	HMDB
alpha-CEHC	MeSH

Chemical Formula

C₁₆H₂₂O₄

Average Molecular Weight

278.3435

Monoisotopic Molecular Weight

278.151809192

IUPAC Name

3-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid

Traditional Name

α-cehc

CAS Registry Number

4072-32-6

SMILES

CC1=C(O)C(C)=C2CCC(C)(CCC(O)=O)OC2=C1C

InChI Identifier

InChI=1S/C16H22O4/c1-9-10(2)15-12(11(3)14(9)19)5-7-16(4,20-15)8-6-13(17)18/h19H,5-8H2,1-4H3,(H,17,18)

InChI Key

AXODOWFEFKOVSH-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Alkyl aryl ether
Benzenoid
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-11962 )

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	2.9	ALOGPS
logP	3.88	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.38 m³·mol⁻¹	ChemAxon
Polarizability	30.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08iu-4090000000-8ca9dbe51872599f7689	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0ab9-9104300000-89eb4eb596d64c263298	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
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0090000000-5984299071d9bd578a66	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0940000000-e94cb5537d42ecca8f25	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0490000000-5a4d681fd73f355a6058	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0930000000-b419f254c71bb6124ca1	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-07br-2900000000-5c87bdb630cb5c9afc3e	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-eb3543747e604b52ab09	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bw9-1490000000-1c600a1fe465c3eb7993	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9810000000-c76ff537508835c548e2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0190000000-5a9a1904b542c448007a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0790000000-0ce3fe0382fcea303038	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-7900000000-805173297214fa41fc0a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-54b37056d244a02c63ec	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-34fb2875b590a256850b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02tc-2490000000-b524618831ea011c0e2a	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28342601	details

External Links

HMDB ID

HMDB0001518

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022669

KNApSAcK ID

Not Available

Chemspider ID

8119154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9943542

PDB ID

Not Available

ChEBI ID

626842

References

Synthesis Reference

Pope, Simon A. S.; Burtin, Guillaume E.; Clayton, Peter T.; Madge, David J.; Muller, David P. R. Synthesis and analysis of conjugates of the major vitamin E metabolite, a-CEHC. Free Radical Biology & Medicine (2002), 33(6), 807-817.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Alpha-CEHC (BMDB0001518)

Structure for BMDB0001518 (Alpha-CEHC)