Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate)
metabolite

Showing entry for Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate)

Identification

PhytoHub ID
PHUB000913
Name
Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate)
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
655.76
Monoisotopic Mass
655.277480455
Chemical Formula
C30H45N3O11S
IUPAC Name
2-amino-4-{[1-(carboxymethylcarbamoyl)-2-{[(1S,12S,17R)-6,10,17-trihydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-5(9)-en-7-yl]sulfanyl}ethyl]carbamoyl}butanoic acid
InChI Key
CWHSNVYWYFOEQJ-XOOUWMDMSA-N
InChI Identifier
InChI=1S/C30H45N3O11S/c1-28-9-18(35)24-22(15(28)6-7-29-8-14(2-4-19(28)29)30(43,12-29)13-34)23(39)27(44-24)45-11-17(25(40)32-10-21(37)38)33-20(36)5-3-16(31)26(41)42/h14-19,23,27,34-35,39,43H,2-13,31H2,1H3,(H,32,40)(H,33,36)(H,37,38)(H,41,42)/t14?,15?,16?,17?,18?,19?,23?,27?,28-,29+,30+/m1/s1
SMILES
C[[email protected]@]12CC(O)C3=C(C(O)C(O3)SCC(NC(=O)CCC(N)C(O)=O)C(=O)NCC(O)=O)C1CC[[email protected]@]13CC(CCC21)[[email protected]@](O)(CO)C3
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
4.18e-01 g/l
LogS (ALOGPS)
-3.20
LogP (ALOGPS)
-3.08
Hydrogen Acceptors
12
Hydrogen Donors
9
Rotatable Bond Count
12
Polar Surface Area
248.96999999999994
Refractivity
159.88000000000005
Polarizability
68.34345255860144
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
9.311345895281136
pKa (strongest acidic)
1.781959152250963
Number of Rings
5
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
Yes

Taxonomy as Metabolite

Family
Terpenoid metabolites
Class
Diterpenoid metabolites
Sub-class
Not Available

Taxonomy of its Precursor(s)

PrecursorFamilyClassSub-class
CafestolTerpenoidsDiterpenoidsNot AvailableShow Precursor

Spectra

No spectra information available

Food Sources

No food source information available

Food Sources of its Precursor(s)

PrecursorFood SourceFood Source Group
CafestolArabica coffeeCoffee and coffee products PublicationsShow
CafestolArabica coffee oilCoffee and coffee products PublicationsShow
CafestolCoffeeCoffee and coffee products PublicationsShow
CafestolRobusta coffeeCoffee and coffee products PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Cafestol Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate)mousebileunknownNot AvailableNot AvailableNot AvailableC30H45N3O11S655.277480455 Publications

Inter-Individual Variations Metabolism

No inter-individual variations available

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