metabolite

Showing entry for 4-Caffeoylquinic-1,5-lactone

Identification

PhytoHub ID
PHUB002471
Name
4-Caffeoylquinic-1,5-lactone
Systematic Name
4-Caffeoylquinic-1,5-lactone
Synonyms
  • 4-Caffeoyl-1,5-quinolactone
CAS Number
Not Available
Average Mass
336.296
Monoisotopic Mass
336.084517475
Chemical Formula
C16H16O8
IUPAC Name
(1S,3R,4R,5R)-1,3-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
InChI Key
BMSNCTFPYHTXGU-JUHZACGLSA-N
InChI Identifier
InChI=1S/C16H16O8/c17-9-3-1-8(5-10(9)18)2-4-13(20)24-14-11(19)6-16(22)7-12(14)23-15(16)21/h1-5,11-12,14,17-19,22H,6-7H2/b4-2+/t11-,12-,14-,16+/m1/s1
SMILES
O[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
2.71e+00 g/l
LogS (ALOGPS)
-2.09
LogP (ALOGPS)
0.20
Hydrogen Acceptors
6
Hydrogen Donors
4
Rotatable Bond Count
4
Polar Surface Area
133.52
Refractivity
79.74250000000002
Polarizability
31.89933121543706
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-3.2468774105273144
pKa (strongest acidic)
9.208140363085006
Number of Rings
3
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Cinnamic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical

Spectra from Online Resources

No spectra information available

Spectra from Phytohub

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0917000000-cb8046a0df2dcea4c30c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i9-0901000000-3ab43acd2192f4bff2db2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-2900000000-5978440cfce3eb4bb0212016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0719000000-bca01da6d33ba1223a6b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0770-0901000000-fe77e7fdb32c939f9ab52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fu-2900000000-c3bc7f82cc7a007f389b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-b526b2a51afa8deb414c2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0906000000-026216b64d723e673db92021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-3910000000-be6b27dd1a97b0f0e0a82021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0109000000-f8be02ae1a18ee0311432021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0944000000-43c604d4a3d2303a7bcd2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03y1-2900000000-277eb7f9c13bcf28c2262021-09-25View Spectrum

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

No food source information available of its precursor(s)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Coffee Chlorogenic acids 4-Caffeoylquinic-1,5-lactonehumanplasmahost metabolism1h-3h<20 nmol/LNot AvailableC16H16O8336.084517475 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Back