Identification

PhytoHub ID
PHUB000010
Name
Kahweol
Systematic Name
Not Available
Synonyms
Not Available
CAS Number
Not Available
Average Mass
314.425
Monoisotopic Mass
314.188194697
Chemical Formula
C20H26O3
IUPAC Name
(1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6,10-trien-17-ol
InChI Key
JEKMKNDURXDJAD-HWUKTEKMSA-N
InChI Identifier
InChI=1S/C20H26O3/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/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1
SMILES
C[[email protected]@]12C=CC3=C(C=CO3)[[email protected]]1CC[[email protected]@]13C[[email protected]@H](CC[[email protected]@H]21)[[email protected]@](O)(CO)C3
Structure

Calculated Properties

Solubility (ALOGPS)
2.01e-02 g/l
LogS (ALOGPS)
-4.19
LogP (ALOGPS)
2.97
Hydrogen Acceptors
2
Hydrogen Donors
2
Rotatable Bond Count
1
Polar Surface Area
53.60000000000001
Refractivity
89.51269999999998
Polarizability
35.49468732619253
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-2.7926234671860763
pKa (strongest acidic)
13.685413916695513
Number of Rings
5
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy

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", "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", "Cyclic alcohol", "Furan", "Heteroaromatic compound", "Hydrocarbon derivative", "Naphthofuran", "Organic oxygen compound", "Organooxygen compound", "Oxacycle", "Primary alcohol", "Tertiary alcohol"]

Spectra

No spectra information available

Food Sources

NameGroup
Arabica coffeeCoffee and coffee products PublicationsShow
CoffeeCoffee and coffee products PublicationsShow
Robusta coffeeCoffee and coffee products PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
Kahweol Kahweol glucuronidehumanurine (minor)host metabolismC26H34O9490.5518874 Publications
Kahweol Kahweol sulfatehumanurine (minor)host metabolismC20H26O6S394.4883325 Publications
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