Cafestol
precursor
Showing entry for Cafestol
Identification
- PhytoHub ID
- PHUB000006
- Name
- Cafestol
- Systematic Name
- Not Available
- Synonyms
- (−)-cafestol
- Cafesterol
- CAS Number
- 469-83-0
- Average Mass
- 316.441
- Monoisotopic Mass
- 316.203844762
- Chemical Formula
- C20H28O3
- IUPAC Name
- (1S,4S,12S,13R,16S,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6-dien-17-ol
- InChI Key
- DNJVYWXIDISQRD-JTSSGKSMSA-N
- InChI Identifier
InChI=1S/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15+,17-,18+,19-,20-/m0/s1
- SMILES
C[[email protected]@]12CCC3=C(C=CO3)[[email protected]]1CC[[email protected]@]13C[[email protected]](CC[[email protected]@H]21)[[email protected]@](O)(CO)C3
- Structure
Calculated Properties
- Solubility (ALOGPS)
- 1.80e-02 g/l
- LogS (ALOGPS)
- -4.24
- LogP (ALOGPS)
- 3.04
- Hydrogen Acceptors
- 2
- Hydrogen Donors
- 2
- Rotatable Bond Count
- 1
- Polar Surface Area
- 53.60000000000001
- Refractivity
- 88.55009999999999
- Polarizability
- 75.87981266270646
- Formal Charge
- 0
- Physiological Charge
- 0
- pKa (strongest basic)
- -2.7454146697920976
- pKa (strongest acidic)
- 13.685426593369503
- Number of Rings
- 5
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- Yes
- Veber's Rule
- No
- MDDR-like Rule
- No
Taxonomy as Precursor
- Family
- Terpenoids
- Class
- Diterpenoids
- Sub-class
- Not Available
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Naphthofurans
- Super-class
- Organoheterocyclic compounds
- Sub-class
- Not Available
- Direct Parent Name
- Naphthofurans
- Alternative Parent Names
- ["1,2-diols", "Benzofurans", "Cyclic alcohols and derivatives", "Furans", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Oxacyclic compounds", "Primary alcohols", "Tertiary alcohols"]
- External Descriptor Annotations
- Not Available
- Substituent Names
- ["1,2-diol", "Alcohol", "Aromatic heteropolycyclic compound", "Benzofuran", "Cyclic alcohol", "Furan", "Heteroaromatic compound", "Hydrocarbon derivative", "Naphthofuran", "Organic oxygen compound", "Organooxygen compound", "Oxacycle", "Primary alcohol", "Tertiary alcohol"]
Spectra from Online Resources
No spectra information available
Food Sources
Name | Group | |||
---|---|---|---|---|
Arabica coffee | Coffee and coffee products | Publications | Show | |
Arabica coffee oil | Coffee and coffee products | Publications | Show | |
Coffee | Coffee and coffee products | Publications | Show | |
Robusta coffee | Coffee and coffee products | Publications | Show |
Metabolism
Precursor | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Cafestol | Cafestol | human | urine | unchanged | Not Available | Not Available | 1-5% | C20H28O3 | 316.203844762 | Detailed Intervention Studies | |||
Cafestol | Cafestol (2-hydroxy-, 3,4-epoxide, glutathione conjugate) | mouse | bile | unknown | Not Available | Not Available | Not Available | C30H45N3O11S | 655.277480455 | Publications | |||
Cafestol | Cafestol (2-hydroxy-) | mouse | bile | unknown | Not Available | Not Available | Not Available | C20H28O4 | 332.198759382 | Publications | |||
Cafestol | Cafestol (2-hydroxy-,3,4-epoxide) | mouse | bile | unknown | Not Available | Not Available | Not Available | C20H28O5 | 348.193674002 | Publications | |||
Cafestol | Cafestol glucuronide | human mouse | bile, blood, urine | host metabolism | Not Available | Not Available | Not Available | C26H36O9 | 492.5678392 | Publications | |||
Cafestol | Cafestol sulfate | human | urine | host metabolism | Not Available | Not Available | Not Available | C20H28O6S | 396.5042844 | Publications |
Inter-Individual Variations Metabolism
No data on inter-individual variations available