Daphnoretin

Details

• Internal ID: 13654d06-c350-481f-a0ad-455277654cee
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 7-hydroxy-6-methoxy-3-(2-oxochromen-7-yl)oxychromen-2-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C=C(C(=O)O2)OC3=CC4=C(C=C3)C=CC(=O)O4)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C=C(C(=O)O2)OC3=CC4=C(C=C3)C=CC(=O)O4)O
• InChI: InChI=1S/C19H12O7/c1-23-16-6-11-7-17(19(22)26-15(11)9-13(16)20)24-12-4-2-10-3-5-18(21)25-14(10)8-12/h2-9,20H,1H3
• InChI Key: JRHMMVBOTXEHGJ-UHFFFAOYSA-N
• Popularity: 135 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₂O₇
• Molecular Weight: 352.30 g/mol
• Exact Mass: 352.05830272 g/mol
• Topological Polar Surface Area (TPSA): 91.30 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 2034-69-7
• Thymelol
• Dephnoretin
• NSC 291852
• NSC-291852
• Dephnoretin;Thymelol
• CHEBI:4324
• COUMARIN, 7-HYDROXY-6-METHOXY-3,7'-OXYDI-
• C19H12O7
• BRN 1299325
• 1A7Q3KY3LH
• 2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy-3-((2-oxo-2H-1-benzopyran-7-yl)oxy)-
• CHEMBL508494
• 7-hydroxy-6-methoxy-3-(2-oxochromen-7-yl)oxychromen-2-one
• 7-hydroxy-6-methoxy-3,7'-dicoumaryl ether
• 7-hydroxy-6-methoxy-3-(2-oxochromen-7-yl)oxy-chromen-2-one
• 7-hydroxy-6-methoxy-3-((2-oxo-2H-chromen-7-yl)oxy)-2H-chromen-2-one
• 2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy-3-[(2-oxo-2H-1-benzopyran-7-yl)oxy]-
• SMR000156224
• 7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one
• UNII-1A7Q3KY3LH
• TimTec1_001767
• Oprea1_038414
• MLS000574856
• MLS000728531
• MLS001048954
• SCHEMBL13784417
• DTXSID00174250
• JRHMMVBOTXEHGJ-UHFFFAOYSA-N
• 7-hydroxy-6-methoxy-3-(2-oxochromen-7-yloxy)chromen-2-one
• HMS1539A07
• HMS2270K03
• HY-N0699
• TNP00178
• BDBM50241949
• MFCD01082318
• NSC291852
• s3289
• AKOS002134405
• NCGC00017271-01
• NCGC00017271-02
• NCGC00142383-01
• AC-34889
• LS-55218
• MS-25454
• CS-0009716
• FT-0697970
• 7-hydroxy-6-methoxy-3,7''-dicoumaryl ether
• C09216
• A879700
• Q-100250
• BRD-K81282485-001-01-3
• Q15410902
• 2-hydroxy-6-methoxy-3-(2-oxochromen-7-yl)oxychromen-7-one
• 1-benzoyl-6-{[4-(2,3-dimethylphenyl)piperazin-1-yl]carbonyl}indoline
• 7-HYDROXY-6-METHOXY-3-((2-OXO-2H-1-BENZOPYRAN-7-YL)OXY)-2H-1-BENZOPYRAN-2-ONE
• Coumarin, 7-hydroxy-6-methoxy-3,7'-oxydi-; 7-Hydroxy-6-methoxy-3-[(2-oxo-2H-1-benzopyran 7-yl)-oxy]-2H-1-benzopyran-2-one; Thymerol; Dephnoretin

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9493	94.93%
Caco-2	-	0.5519	55.19%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7332	73.32%
OATP2B1 inhibitior	-	0.7171	71.71%
OATP1B1 inhibitior	+	0.8595	85.95%
OATP1B3 inhibitior	+	0.9888	98.88%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4742	47.42%
P-glycoprotein inhibitior	+	0.7126	71.26%
P-glycoprotein substrate	-	0.8821	88.21%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8283	82.83%
CYP2D6 substrate	-	0.8191	81.91%
CYP3A4 inhibition	-	0.8440	84.40%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9305	93.05%
CYP1A2 inhibition	+	0.7468	74.68%
CYP2C8 inhibition	+	0.4538	45.38%
CYP inhibitory promiscuity	-	0.8566	85.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4852	48.52%
Eye corrosion	-	0.9689	96.89%
Eye irritation	-	0.7542	75.42%
Skin irritation	-	0.6003	60.03%
Skin corrosion	-	0.9665	96.65%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6615	66.15%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.8049	80.49%
skin sensitisation	-	0.9270	92.70%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5159	51.59%
Acute Oral Toxicity (c)	III	0.6713	67.13%
Estrogen receptor binding	+	0.9392	93.92%
Androgen receptor binding	+	0.7655	76.55%
Thyroid receptor binding	-	0.5669	56.69%
Glucocorticoid receptor binding	+	0.8662	86.62%
Aromatase binding	+	0.6852	68.52%
PPAR gamma	+	0.8295	82.95%
Honey bee toxicity	-	0.8929	89.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6049	60.49%
Fish aquatic toxicity	+	0.9036	90.36%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	35481.3 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM; 17782.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	501.2 nM; 501.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	44668.4 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM; 35481.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	44668.4 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	35481.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.60%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.61%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.66%	99.15%
CHEMBL4208	P20618	Proteasome component C5	90.59%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.55%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.52%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.54%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.74%	86.33%
CHEMBL2535	P11166	Glucose transporter	82.97%	98.75%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.32%	93.65%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.15%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.07%	85.14%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.05%	80.78%
CHEMBL3194	P02766	Transthyretin	80.58%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.06%	96.00%

Plants that contains it

• Acer caudatifolium
• Aconitum heterophyllum
• Agathis lanceolata
• Artemisia keiskeana
• Astragalus sinicus
• Baccharis macraei
• Boenninghausenia albiflora
• Carthamus tinctorius
• Coronilla scorpioides
• Coronilla vaginalis
• Coronilla valentina subsp. glauca
• Cynoglossum lanceolatum
• Daphne acutiloba
• Daphne bholua
• Daphne genkwa
• Daphne gnidioides
• Daphne gnidium
• Daphne mezereum
• Daphne odora
• Daphne sericea
• Diarthron vesiculosum
• Dirca occidentalis
• Dracaena concinna
• Edgeworthia chrysantha
• Edgeworthia gardneri
• Enkleia malaccensis
• Euphorbia ebracteolata
• Euphorbia fischeriana
• Isodon amethystoides
• Klasea centauroides subsp. strangulata
• Leucoptera nodosa
• Lindera glauca
• Linostoma pauciflorum
• Marshallia graminifolia
• Mikania goyazensis
• Neolitsea pulchella
• Oxytropis ochrocephala
• Peddiea fischeri
• Rumohra adiantiformis
• Ruta corsica
• Ruta graveolens
• Ruta montana
• Salacia cordata
• Stellera chamaejasme
• Stenocephalum megapotamicum
• Syzygium sandwicense
• Thymelaea hirsuta
• Trifolium pratense
• Vigna angularis
• Wikstroemia elliptica
• Wikstroemia glabra
• Wikstroemia hainanensis
• Wikstroemia indica
• Wikstroemia lanceolata
• Wikstroemia retusa
• Wikstroemia sikokiana
• Wikstroemia uva-ursi

Cross-Links

• PubChem: 5281406
• NPASS: NPC231149
• ChEMBL: CHEMBL508494
• LOTUS: LTS0157584
• wikiData: Q15410902