Isorhamnetin (YMDB01720)

Identification

YMDB ID

YMDB01720

Name

Isorhamnetin

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Isorhamnetin, also known as 3-methylquercetin, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, isorhamnetin is considered to be a flavonoid. Isorhamnetin exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Isorhamnetin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Isorhamnetol
3,5,7,4'-Tetrahydroxy-3'-methoxyflavone
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-benzopyran-4-one
3-Methylquercetin
Quercetin 3'-methyl ether
3'-Methoxy-3,4',5,7-tetrahydroxyflavone
3'-Methoxyquercetin
3'-Methylquercetin
3'-O-Methylquercetin
3,4',5,7-Tetrahydroxy-3'-methoxy-flavone
3,4',5,7-Tetrahydroxy-3'-methoxyflavone
3-Methylquercetine
4'-Methoxyquercetin
4'-Methylquercetin
4'-O-Methylquercetin
3-O-Methylquercetin
iso-Rhamnetin
Isorhamnetine
3-Methyl-quercetin
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
3,4’,5,7-Tetrahydroxy-3’-methoxyflavone
3’-Methoxyquercetin
3’-Methylquercetin
3’-O-Methylquercetin
Quercetin 3’-methyl ether

CAS number

480-19-3

Weight

Average: 316.2623
Monoisotopic: 316.058302738

InChI Key

IZQSVPBOUDKVDZ-UHFFFAOYSA-N

InChI

InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

Traditional IUPAC Name

isorhamnetin

Chemical Formula

C₁₆H₁₂O₇

SMILES

COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:6052 )
tetrahydroxyflavone (CHEBI:6052 )
7-hydroxyflavonol (CHEBI:6052 )
flavonols (C10084 )
Flavones and Flavonols (C10084 )
Flavones and Flavonols (LMPK12110002 )

Physical Properties

State

Solid

Charge

Melting point

311-314 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	1.96	ALOGPS
logP	2.3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.34 m³·mol⁻¹	ChemAxon
Polarizability	30.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Bitter	FDB000604

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-2219000000-20feeef38553ee7cdd29	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-2219000000-20feeef38553ee7cdd29	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0591000000-2e1f6e28bf0d47d5e240	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001u-0041090000-7e13d91dc4b2bd93fc17	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0udi-0394000000-f903b8df9b79e6a94f44	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0udi-0956000000-6286c6784746c9eba0e8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gb9-0219000000-c620190cc3878a4242f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-1941000000-10313269e61a0584f37f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gb9-0109000000-082620470bd7fd8a6897	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ufr-0491000000-da6ec11ed89cc64a7972	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0139000000-141b68c1e564685b35ce	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0139000000-8fa57905e16cdfcc4e9e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0493000000-2b88769e97319b5f076c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0udi-1940000000-51e0d426523f81faa98b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0gb9-0009000000-caca1c7784ed9828dfb4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-0233e63233dadf52ffc5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0zfr-0952000000-13e1d438b3f800cfc18a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0209000000-89d7fc697d82018c1228	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0gb9-0209000000-405d086d8e4de2b975b1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-0a4i-1910000000-170b80b866f2075e44e9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0029000000-a9da21c499e339f09ac6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0493000000-14bbb49d59d91543a76e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0029000000-3458ddb4f7ba64eb81c8	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0019000000-bb7cbcffdd9f296b6b9b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0079000000-c73663231834b1b1b79a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uds-3790000000-3b8ca78684ffcba51bf1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-57dd2505d869c8f411dc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0169000000-38b50b4081dff638023b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0frb-3890000000-3525a3f4676b6a964b71	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	6052
HMDB ID	HMDB02655
Pubchem Compound ID	5281654
Kegg ID	C10084
ChemSpider ID	4444973
FOODB ID	FDB000604
Wikipedia ID	Isorhamnetin
BioCyc ID	Not Available

Structure for #<Compound:0x9b504c18>