General
Preferred name
(+/-)-Eriodictyol
Synonyms
ERIODYCTOL ()
Huazhongilexone ()
(±)-Huazhongilexone ()
Dihydroluteolin ()
(±)-Eriodictyol ()
P&D ID
PD000600
CAS
4049-38-1
Tags
available
natural product
Structure
PD000600
(+/-)-Eriodictyol
RO5
MW
288.06
HBA
6
HBD
4
RB
1
LOGP
2.22
56
4
0
20
Structure formats
SMILES
O=C1CC(c2ccc(O)c(O)c2)Oc2cc(O)cc(O)c21
InChI
InChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2
InChIkey
SBHXYTNGIZCORC-UHFFFAOYSA-N
MOL
(+/-)-Eriodictyol RDKit 2D 21 23 0 0 0 0 0 0 0 0999 V2000 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 2 0 4 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 16 18 2 0 18 19 1 0 19 20 1 0 19 21 2 0 21 2 1 0 12 5 1 0 21 14 1 0 M END > <ID> PD000600 > <Name> (+/-)-Eriodictyol
Description
(extracted from source data)
DESCRIPTION Eriodictyol is a natural plant compound that is present in Prunus campanulata (cherry tree) and Lawsonia inermis (henna tree). (GtoPdb)
DESCRIPTION Endogenous retinoic acid receptor agonist (Tocris Bioactive Compound Library)
Protein targets
20
8.1
MAPK1 Mitogen-activated protein kinase 1 BIOCHEM 75.9x
62
1
6.22
CYP19A1 Aromatase
3
1
5
ALOX15 Polyunsaturated fatty acid lipoxygenase ALOX15
10
1
4.95
PKM Pyruvate kinase PKM
4
1
4.9
GAA Lysosomal alpha-glucosidase
3
1
4.9
HPGD 15-hydroxyprostaglandin dehydrogenase [NAD(+)]
4
1
4.8
APEX1 DNA repair nuclease/redox regulator APEX1
6
1
4.57
KDM4E Lysine-specific demethylase 4E
1
1
4.55
MAPT Microtubule-associated protein tau
3
1
4.5
ALDH1A1 Aldehyde dehydrogenase 1A1
3
1
4.45
POLB DNA polymerase beta
7
1
4.45
RECQL ATP-dependent DNA helicase Q1
0
1
4.4
TGR thioredoxin-disulfide reductase
0
1
4.4
CYP3A4 Cytochrome P450 3A4
7
1
4.4
HSD17B10 3-hydroxyacyl-CoA dehydrogenase type-2
5
1
4.3
ALPI Intestinal-type alkaline phosphatase
3
2
4.27
ALPI Intestinal-type alkaline phosphatase 1
0
1
4.22
ALPG Alkaline phosphatase, germ cell type
1
2
4.21
TAS2R14 Taste receptor type 2 member 14 agonist
3
1
4.09
ALPL Alkaline phosphatase, tissue-nonspecific isozyme
1
2
Target pathways
117
Abasic sugar-phosphate removal via the single-nucleotide replacement pathway
R-HSA-73930
POLB
APEX1
Activation of AMPK downstream of NMDARs
R-HSA-9619483
MAPT
Activation of the AP-1 family of transcription factors
R-HSA-450341
MAPK1
Advanced glycosylation endproduct receptor signaling
R-HSA-879415
MAPK1
Aflatoxin activation and detoxification
R-HSA-5423646
CYP3A4
APEX1-Independent Resolution of AP Sites via the Single Nucleotide Replacement Pathway
R-HSA-5649702
POLB
Aspirin ADME
R-HSA-9749641
CYP3A4
Atorvastatin ADME
R-HSA-9754706
CYP3A4
Biosynthesis of D-series resolvins
R-HSA-9018676
HPGD
Biosynthesis of DHA-derived SPMs
R-HSA-9018677
ALOX15
Biosynthesis of DPAn-3-derived protectins and resolvins
R-HSA-9026286
ALOX15
Biosynthesis of DPAn-6 SPMs
R-HSA-9025106
ALOX15
Biosynthesis of E-series 18(R)-resolvins
R-HSA-9023661
ALOX15
Biosynthesis of E-series 18(S)-resolvins
R-HSA-9018896
ALOX15
HPGD
Biosynthesis of Lipoxins (LX)
R-HSA-2142700
HPGD
Biosynthesis of maresin-like SPMs
R-HSA-9027307
CYP3A4
Biosynthesis of protectins
R-HSA-9018681
ALOX15
Branched-chain amino acid catabolism
R-HSA-70895
HSD17B10
Caspase-mediated cleavage of cytoskeletal proteins
R-HSA-264870
MAPT
Class C/3 (Metabotropic glutamate/pheromone receptors)
R-HSA-420499
TAS2R14
Defective CYP19A1 causes AEXS
R-HSA-5579030
CYP19A1
Digestion
R-HSA-8935690
ALPI
Displacement of DNA glycosylase by APEX1
R-HSA-110357
APEX1
Downregulation of SMAD2/3:SMAD4 transcriptional activity
R-HSA-2173795
MAPK1
Endogenous sterols
R-HSA-211976
CYP19A1
ERK/MAPK targets
R-HSA-198753
MAPK1
ERKs are inactivated
R-HSA-202670
MAPK1
ESR-mediated signaling
R-HSA-8939211
MAPK1
Estrogen biosynthesis
R-HSA-193144
CYP19A1
Estrogen-dependent nuclear events downstream of ESR-membrane signaling
R-HSA-9634638
MAPK1
Estrogen-stimulated signaling through PRKCZ
R-HSA-9634635
MAPK1
Ethanol oxidation
R-HSA-71384
ALDH1A1
FCERI mediated MAPK activation
R-HSA-2871796
MAPK1
FCGR3A-mediated phagocytosis
R-HSA-9664422
MAPK1
Frs2-mediated activation
R-HSA-170968
MAPK1
Fructose catabolism
R-HSA-70350
ALDH1A1
G alpha (i) signalling events
R-HSA-418594
TAS2R14
Gastrin-CREB signalling pathway via PKC and MAPK
R-HSA-881907
MAPK1
Glycogen breakdown (glycogenolysis)
R-HSA-70221
GAA
Glycogen storage disease type II (GAA)
R-HSA-5357609
GAA
Glycolysis
R-HSA-70171
PKM
Golgi Cisternae Pericentriolar Stack Reorganization
R-HSA-162658
MAPK1
Growth hormone receptor signaling
R-HSA-982772
MAPK1
IFNG signaling activates MAPKs
R-HSA-9732724
MAPK1
Interferon gamma signaling
R-HSA-877300
MAPK1
Interleukin-4 and Interleukin-13 signaling
R-HSA-6785807
ALOX15
MAP2K and MAPK activation
R-HSA-5674135
MAPK1
MAPK1 (ERK2) activation
R-HSA-112411
MAPK1
Mitochondrial protein degradation
R-HSA-9837999
HSD17B10
NCAM signaling for neurite out-growth
R-HSA-375165
MAPK1
Negative feedback regulation of MAPK pathway
R-HSA-5674499
MAPK1
Negative regulation of FGFR1 signaling
R-HSA-5654726
MAPK1
Negative regulation of FGFR2 signaling
R-HSA-5654727
MAPK1
Negative regulation of FGFR3 signaling
R-HSA-5654732
MAPK1
Negative regulation of FGFR4 signaling
R-HSA-5654733
MAPK1
Negative regulation of MAPK pathway
R-HSA-5675221
MAPK1
Neutrophil degranulation
R-HSA-6798695
MAPK1
GAA
PKM
NPAS4 regulates expression of target genes
R-HSA-9768919
MAPK1
Nuclear events stimulated by ALK signaling in cancer
R-HSA-9725371
MAPK1
Oncogene Induced Senescence
R-HSA-2559585
MAPK1
Oxidative Stress Induced Senescence
R-HSA-2559580
MAPK1
Paradoxical activation of RAF signaling by kinase inactive BRAF
R-HSA-6802955
MAPK1
PCNA-Dependent Long Patch Base Excision Repair
R-HSA-5651801
POLB
APEX1
Phase I - Functionalization of compounds
R-HSA-211945
CYP3A4
phospho-PLA2 pathway
R-HSA-111995
MAPK1
PI5P, PP2A and IER3 Regulate PI3K/AKT Signaling
R-HSA-6811558
MAPK1
PKR-mediated signaling
R-HSA-9833482
MAPT
POLB-Dependent Long Patch Base Excision Repair
R-HSA-110362
POLB
APEX1
Post-translational modification: synthesis of GPI-anchored proteins
R-HSA-163125
ALPL
ALPI
ALPG
Prednisone ADME
R-HSA-9757110
CYP3A4
Pyruvate metabolism
R-HSA-70268
PKM
RA biosynthesis pathway
R-HSA-5365859
ALDH1A1
RAF-independent MAPK1/3 activation
R-HSA-112409
MAPK1
RAF/MAP kinase cascade
R-HSA-5673001
MAPK1
Recycling pathway of L1
R-HSA-437239
MAPK1
Regulation of actin dynamics for phagocytic cup formation
R-HSA-2029482
MAPK1
Regulation of HSF1-mediated heat shock response
R-HSA-3371453
MAPK1
Regulation of PTEN gene transcription
R-HSA-8943724
MAPK1
Regulation of pyruvate metabolism
R-HSA-9861718
PKM
Regulation of the apoptosome activity
R-HSA-9627069
MAPK1
Resolution of Abasic Sites (AP sites)
R-HSA-73933
APEX1
Resolution of AP sites via the multiple-nucleotide patch replacement pathway
R-HSA-110373
POLB
APEX1
Resolution of AP sites via the single-nucleotide replacement pathway
R-HSA-110381
POLB
RHO GTPases Activate NADPH Oxidases
R-HSA-5668599
MAPK1
RHO GTPases Activate WASPs and WAVEs
R-HSA-5663213
MAPK1
rRNA processing in the mitochondrion
R-HSA-8868766
HSD17B10
RSK activation
R-HSA-444257
MAPK1
RUNX2 regulates osteoblast differentiation
R-HSA-8940973
MAPK1
Senescence-Associated Secretory Phenotype (SASP)
R-HSA-2559582
MAPK1
Sensory perception of sweet, bitter, and umami (glutamate) taste
R-HSA-9717207
TAS2R14
Signal attenuation
R-HSA-74749
MAPK1
Signal transduction by L1
R-HSA-445144
MAPK1
Signaling by Activin
R-HSA-1502540
MAPK1
Signaling by BRAF and RAF1 fusions
R-HSA-6802952
MAPK1
Signaling by high-kinase activity BRAF mutants
R-HSA-6802948
MAPK1
Signaling by LTK in cancer
R-HSA-9842640
MAPK1
Signaling by MAP2K mutants
R-HSA-9652169
MAPK1
Signaling by MAPK mutants
R-HSA-9652817
MAPK1
Signaling by moderate kinase activity BRAF mutants
R-HSA-6802946
MAPK1
Signaling by NODAL
R-HSA-1181150
MAPK1
Signaling by RAF1 mutants
R-HSA-9656223
MAPK1
Signaling downstream of RAS mutants
R-HSA-9649948
MAPK1
SMAD2/SMAD3:SMAD4 heterotrimer regulates transcription
R-HSA-2173796
MAPK1
Spry regulation of FGF signaling
R-HSA-1295596
MAPK1
Suppression of apoptosis
R-HSA-9635465
MAPK1
Synthesis of 12-eicosatetraenoic acid derivatives
R-HSA-2142712
ALOX15
Synthesis of 15-eicosatetraenoic acid derivatives
R-HSA-2142770
ALOX15
Synthesis of Leukotrienes (LT) and Eoxins (EX)
R-HSA-2142691
ALOX15
Synthesis of PA
R-HSA-1483166
ALPI
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)
R-HSA-2162123
HPGD
Thrombin signalling through proteinase activated receptors (PARs)
R-HSA-456926
MAPK1
Transcriptional and post-translational regulation of MITF-M expression and activity
R-HSA-9856649
MAPK1
tRNA modification in the mitochondrion
R-HSA-6787450
HSD17B10
tRNA processing in the mitochondrion
R-HSA-6785470
HSD17B10
Ub-specific processing proteases
R-HSA-5689880
POLB
Xenobiotics
R-HSA-211981
CYP3A4
Zygotic genome activation (ZGA)
R-HSA-9819196
KDM4E
References
10
Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity (dataset)
2017 Combating breast cancer with non-steroidal aromatase inhibitors (NSAIs): Understanding the chemico-biological interactions through comparative SAR/QSAR study.
Adhikari N, Amin SA et al. Eur J Med Chem
2013 Bitter taste receptor activation by flavonoids and isoflavonoids: modeled structural requirements for activation of hTAS2R14 and hTAS2R39.
Roland WS, van Buren L et al. J Agric Food Chem
2013 Modulation of human neutrophils' oxidative burst by flavonoids.
Ribeiro D, Freitas M et al. Eur. J. Med. Chem.
PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors and Activators of N370S glucocerebrosidase as a Potential Chaperone Treatment of Gaucher Disease: Purified N370S Glucocerebrosidase. (Class of assay: confirmatory) [Related pubchem assays: 2101 ] AID 2597
AID 434954
AID 488783
AID 488873
AID 488878
AID 488880
Cell lines
1
4.75
Neutrophil
Organisms
0
Compound Sets
4
Concise Guide to Pharmacology 2023/24
12442
Guide to Pharmacology
12442
MedChem Express Bioactive Compound Library
HY-N0637A
Tocris Bioactive Compound Library
7199
Available from
4
Mcule
MCULE-8678602121
MedChem Express Bioactive Compound Library
HY-N0637A
MolPort
MolPort-001-740-726
Molport-001-740-726
Tocris Bioactive Compound Library
7199
External IDs
23
ChEMBL CHEMBL307893
GtoPdb 12442
PubChem 11095
BindingDB 69393
Brenda 53695 124113 193557
ChEBI 91645
ChemicalBook CB51033787
ChemSpider 10624
eMolecules 772212
FDA SRS CQT975GLYF
GSRS 980239a8-b7f7-4...
IBM NIH CF4DC84966F679F...
LINCS LSM-1479
Mcule MCULE-8678602121
MolPort MolPort-001-740-726 Molport-001-740-726
Nikkaji J6.721K
NMRShiftDB 60023914
PubChem TPS 14873285
Reactome 10624
SureChEMBL SCHEMBL2309591
Properties
(calculated by RDKit )
Molecular Weight
288.06
Hydrogen Bond Acceptors
6
Hydrogen Bond Donors
4
Rotatable Bonds
1
Ring Count
3
Aromatic Ring Count
2
cLogP
2.22
TPSA
107.22
Fraction CSP3
0.13
Chiral centers
1.0
Largest ring
6.0
QED
0.6
Structural alerts
0
No structural alerts detected
Custom attributes
(extracted from source data)
Primary Target
TRPV
MOA
Endogenous Metabolite
Keap1-Nrf2
Antagonist
Pathway
Metabolic Enzyme/Protease
NF-¦ÊB
GPCR/G protein
Neuronal Signaling
Target
Melanocortin Receptor
Source data