Identification

PhytoHub ID
PHUB000915
Name
Cafestol (2-hydroxy-,3,4-epoxide)
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
348.439
Monoisotopic Mass
348.193674002
Chemical Formula
C20H28O5
IUPAC Name
(1S,13S,17R,18R)-18-(hydroxymethyl)-13-methyl-7,9-dioxahexacyclo[15.2.1.0^{1,14}.0^{4,13}.0^{5,10}.0^{6,8}]icos-5(10)-ene-11,18-diol
InChI Key
HTBXMMAMMYSHPY-UTHCWJHUSA-N
InChI Identifier
InChI=1S/C20H28O5/c1-18-7-12(22)15-14(16-17(24-15)25-16)11(18)4-5-19-6-10(2-3-13(18)19)20(23,8-19)9-21/h10-13,16-17,21-23H,2-9H2,1H3/t10?,11?,12?,13?,16?,17?,18-,19+,20+/m1/s1
SMILES
C[[email protected]@]12CC(O)C3=C(C4OC4O3)C1CC[[email protected]@]13C[[email protected]@H](CCC21)[[email protected]@](O)(CO)C3
Structure

Calculated Properties

Solubility (ALOGPS)
3.31e-01 g/l
LogS (ALOGPS)
-3.02
LogP (ALOGPS)
0.59
Hydrogen Acceptors
5
Hydrogen Donors
3
Rotatable Bond Count
1
Polar Surface Area
82.45
Refractivity
90.62429999999999
Polarizability
37.57473296615247
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-3.075750749555005
pKa (strongest acidic)
13.469958411618176
Number of Rings
6
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Precursor Taxonomy

PrecursorFamilyClassSub-class
CafestolTerpenoidsDiterpenoidsNot AvailableShow Precursor

Spectra

No spectra information available

Food Sources

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

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
Cafestol Cafestol (2-hydroxy-,3,4-epoxide)mousebileunknownC20H28O5348.193674002 Publications
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