PhytoHub: Showing entry for Isoxanthohumol

Isoxanthohumol

Identification

PhytoHub ID

PHUB000384

Name

Isoxanthohumol

Systematic Name

Not Available

Synonyms

5-Methyl-8-prenylnaringenin
7,4'-Dihydroxy-5-methoxy-8-prenylflavanone

CAS Number

70872-29-6

Average Mass

354.402

Monoisotopic Mass

354.146723808

Chemical Formula

C₂₁H₂₂O₅

IUPAC Name

7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

InChI Key

YKGCBLWILMDSAV-UHFFFAOYSA-N

InChI Identifier

InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3

SMILES

COC1=C2C(=O)CC(OC2=C(CC=C(C)C)C(O)=C1)C1=CC=C(O)C=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.42e-02 g/l
LogS (ALOGPS): -4.40
LogP (ALOGPS): 3.25
Hydrogen Acceptors: 5
Hydrogen Donors: 2
Rotatable Bond Count: 4
Polar Surface Area: 75.99000000000001
Refractivity: 100.01490000000001
Polarizability: 38.07423347262512
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -4.626074648338253
pKa (strongest acidic): 7.6644544444732565
Number of Rings: 3
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 513197
Phenol-Explorer: 224
FooDB (Compounds): FDB012290
PeakForestCompound: 000336

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Miscellaneous flavonoids

Taxonomy as Metabolite

Metabolite Family: (Poly)phenol metabolites
Metabolite Class: Flavonoid metabolites
Metabolite Sub-class: Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Xanthohumol	Polyphenols	Miscellaneous polyphenols	Not Available	Show Food Phytochemical

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

LC-MS/MS	LC-ESI-QTOF	Negative	low	View Spectrum	(233.0848,0.06406406);(353.1438,1.0);(354.1467,0.11611612)
LC-MS/MS	LC-ESI-QTOF	Negative	medium	View Spectrum	(119.0514,0.36636637);(120.0543,0.03003003);(233.0844,1.0);(234.0878,0.07107107);(251.0965,0.03303303);(353.1435,0.31031031);(354.1468,0.05705706)
LC-MS/MS	LC-ESI-QTOF	Negative	medium	View Spectrum	(119.0517,1.0);(120.0544,0.10710711);(133.0684,0.02902903);(163.0057,0.02802803);(165.0927,0.06006006);(175.0092,0.02702703);(189.0916,0.03503504);(218.0603,0.05005005);(233.0846,0.18618619);(234.088,0.02402402)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	low	View Spectrum	(233.085,0.064);(353.144,1.0);(354.147,0.116)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	medium	View Spectrum	(119.052,1.0);(120.054,0.107);(133.068,0.029);(163.006,0.028);(165.093,0.06);(175.009,0.027);(189.092,0.035);(218.06,0.05);(233.085,0.186);(234.088,0.024)
LC-MS/MS	LC-ESI-QTOF	Negative	medium	View Spectrum	(287.1314,0.1041041);(407.1882,1.0);(408.1917,0.18718719);(409.1945,0.02502503)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	medium	View Spectrum	(119.051,0.366);(120.054,0.03);(233.084,1.0);(234.088,0.071);(251.096,0.033);(353.144,0.31);(354.147,0.057)
LC-MS/MS	LC-ESI-QTOF	Negative	medium	View Spectrum	(119.0542,0.19119119);(201.1313,0.02202202);(219.1427,0.02802803);(243.1405,0.08108108);(244.144,0.02102102);(259.1372,0.03103103);(261.1515,0.02202202);(283.0645,0.04804805);(287.1319,1.0);(288.1351,0.14014014);(289.1384,0.02502503);(301.1461,0.04004004);(313.1468,0.04504505);(407.1882,0.41141141);(408.1913,0.09409409)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	low	View Spectrum	(407.188,1.0);(408.192,0.182);(409.194,0.024)
LC-MS/MS	LC-ESI-QTOF	Negative	high	View Spectrum	(119.0542,1.0);(120.0578,0.11111111);(137.0323,0.04304304);(163.0089,0.08008008);(176.0155,0.11211211);(177.0211,0.03903904);(177.1306,0.04404404);(201.1304,0.07907908);(202.1363,0.04204204);(219.141,0.07907908);(243.1409,0.10510511);(283.0635,0.07207207);(287.1328,0.32932933);(288.1344,0.06106106);(301.1478,0.05005005);(407.1939,0.03903904)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	medium	View Spectrum	(287.131,0.104);(407.188,1.0);(408.192,0.187);(409.194,0.025)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	medium	View Spectrum	(119.054,0.191);(201.131,0.022);(219.143,0.028);(243.14,0.081);(244.144,0.021);(259.137,0.031);(261.152,0.022);(283.064,0.048);(287.132,1.0);(288.135,0.14);(289.138,0.025);(301.146,0.04);(313.147,0.045);(407.188,0.411);(408.191,0.094)
LC-MS/MS	LC-ESI-UNKNOWN	Negative	high	View Spectrum	(119.054,1.0);(120.058,0.111);(137.032,0.043);(163.009,0.08);(176.016,0.112);(177.021,0.039);(177.131,0.044);(201.13,0.079);(202.136,0.042);(219.141,0.079);(243.141,0.105);(283.064,0.072);(287.133,0.329);(288.134,0.061);(301.148,0.05);(407.194,0.039)
LC-MS/MS	LC-ESI-QTOF	Negative	low	View Spectrum	(407.1882,1.0);(408.1917,0.18218218);(409.1937,0.02402402)

Food Sources

	Name	Group
	Beer	Beverages, Alcoholic	Publications	Show

Food Sources of its Food Phytochemical(s)

	Food Phytochemical	Food Source	Food Source Group
	Xanthohumol	Beer	Beverages, Alcoholic	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

	Food Phytochemical		Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
	Isoxanthohumol		8-Prenylnaringenin	rat	plasma, urine	Not Available	Not Available	Not Available	Not Available	C₂₀H₂₀O₅	340.131073744		Publications
	Xanthohumol		Isoxanthohumol	human	plasma (major)	Not Available	Not Available	Not Available	Not Available	C₂₁H₂₂O₅	354.146723808		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Isoxanthohumol