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

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

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, glutathione conjugate)mousebileunknownC30H45N3O11S655.277480455 Publications
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