7,8-Dihydroxyflavone

Details

• Internal ID: ef657cc0-75dd-4f2f-b305-3b25cd1e29dc
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 7,8-dihydroxy-2-phenylchromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O
• InChI: InChI=1S/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H
• InChI Key: COCYGNDCWFKTMF-UHFFFAOYSA-N
• Popularity: 370 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24 g/mol
• Exact Mass: 254.05790880 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 38183-03-8
• 7,8-dihydroxy-2-phenyl-4H-chromen-4-one
• 7,8-DHF
• 7,8-Dihydroxyflavone hydrate
• 4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl-
• 7,8-Dihydroxy-flavone
• 7,8-Dihydroxy-2-phenyl-chromen-4-one
• 7,8-dihydroxy-2-phenylchromen-4-one
• 7,8-Dihydroxy-2-phenyl-4-benzopyrone
• EINECS 253-812-4
• ADB6MA8ZV2
• 7,8-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one
• BRN 0234350
• CHEMBL75267
• NSC-750341
• 5-18-04-00079 (Beilstein Handbook Reference)
• MFCD00006836
• 7,8-diOH-Flavone
• Spectrum_001087
• Spectrum2_000952
• Spectrum3_000213
• Spectrum4_001823
• Spectrum5_000585
• UNII-ADB6MA8ZV2
• 8-DHF
• BSPBio_001825
• KBioGR_002491
• KBioSS_001567
• SPECTRUM201315
• BIDD:ER0103
• DivK1c_000371
• SCHEMBL419316
• SPBio_000944
• MEGxp0_001683
• 7,8-dihydroxy-2-phenylchromone
• FEMA NO. 4830
• HMS501C13
• KBio1_000371
• KBio2_001567
• KBio2_004135
• KBio2_006703
• KBio3_001325
• DTXSID00191568
• CHEBI:140464
• NINDS_000371
• HMS1923A03
• HMS3263G12
• HMS3743I05
• HMS3886D10
• BCP14497
• Tox21_501075
• BDBM50093539
• CCG-39038
• DHF, 7,8-
• NSC750341
• s8319
• AKOS015856571
• CS-W014088
• HY-W013372
• NSC 750341
• SDCCGMLS-0066465.P001
• IDI1_000371
• NCGC00095217-01
• NCGC00095217-02
• NCGC00095217-03
• NCGC00095217-12
• NCGC00178976-01
• NCGC00261760-01
• AC-23011
• DS-16246
• LS-39603
• PD002189
• D1916
• FT-0639436
• 7,8-Dihydroxyflavone hydrate, >=98% (HPLC)
• C74948
• 4H-1-Benzopyran-4-one,7,8-dihydroxy-2-phenyl-
• A824039
• SR-05000002499
• SR-05000002499-1
• BRD-K49535716-001-02-4
• BRD-K49535716-001-03-2
• Q19596931
• 2(1H)-Pentalenone, 4,5,6,6a-tetrahydro-1,3-dimethyl-
• 7,8-dihydroxy-2-phenyl-chromen-4-one;7,8-Dihydroxyflavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9569	95.69%
Caco-2	-	0.9057	90.57%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7742	77.42%
OATP2B1 inhibitior	-	0.7051	70.51%
OATP1B1 inhibitior	+	0.9502	95.02%
OATP1B3 inhibitior	+	0.9902	99.02%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7557	75.57%
P-glycoprotein inhibitior	-	0.7967	79.67%
P-glycoprotein substrate	-	0.9206	92.06%
CYP3A4 substrate	-	0.5841	58.41%
CYP2C9 substrate	-	0.8321	83.21%
CYP2D6 substrate	-	0.8118	81.18%
CYP3A4 inhibition	-	0.7054	70.54%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	-	0.6965	69.65%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9249	92.49%
CYP2C8 inhibition	+	0.4579	45.79%
CYP inhibitory promiscuity	-	0.5409	54.09%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5926	59.26%
Eye corrosion	-	0.9890	98.90%
Eye irritation	+	0.9535	95.35%
Skin irritation	+	0.6100	61.00%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9154	91.54%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.5950	59.50%
skin sensitisation	-	0.8006	80.06%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7932	79.32%
Acute Oral Toxicity (c)	II	0.7187	71.87%
Estrogen receptor binding	+	0.9173	91.73%
Androgen receptor binding	+	0.9257	92.57%
Thyroid receptor binding	+	0.6668	66.68%
Glucocorticoid receptor binding	+	0.9486	94.86%
Aromatase binding	+	0.9407	94.07%
PPAR gamma	+	0.9019	90.19%
Honey bee toxicity	-	0.9330	93.30%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9311	93.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	3162.3 nM	Potency	PMID: 18443127
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	3981.1 nM	Potency	PMID: 26260339
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	5011.9 nM	Potency	PMID: 24387625
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; PMID: 19029333
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	PMID: 19419803; DOI: 10.6019/CHEMBL1201861
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	10000 nM	Potency	PMID: 19132934
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	9820 nM	IC50	PMID: 15646539
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	7943.3 nM	Potency	DOI: 10.6019/CHEMBL1201861
CHEMBL4040	P28482	MAP kinase ERK2	2511.9 nM	Potency	PMID: 26186150
CHEMBL1293224	P10636	Microtubule-associated protein tau	31622.8 nM; 28183.8 nM	Potency; Potency	PMID: 12646019; PMID: 22037378
CHEMBL4898	Q16620	Neurotrophic tyrosine kinase receptor type 2	320 nM	Kd	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	35481.3 nM	Potency	DOI: 10.1007/s00044-011-9876-x
CHEMBL2916	O14746	Telomerase reverse transcriptase	36000 nM; 36000 nM	IC50; IC50	PMID: 894684; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.70%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.64%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.22%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.10%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.51%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.69%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.50%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.49%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.29%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.27%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.95%	95.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.55%	93.99%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	81.15%	89.23%

Plants that contains it

• Chrysanthemum morifolium

Cross-Links

• PubChem: 1880
• NPASS: NPC168803
• ChEMBL: CHEMBL75267
• LOTUS: LTS0085963
• wikiData: Q19596931