Diphyllin

Details

• Internal ID: 9d0155f0-fd82-4825-b885-a61eec545414
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3C(=C2O)COC3=O)C4=CC5=C(C=C4)OCO5)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3C(=C2O)COC3=O)C4=CC5=C(C=C4)OCO5)OC
• InChI: InChI=1S/C21H16O7/c1-24-15-6-11-12(7-16(15)25-2)20(22)13-8-26-21(23)19(13)18(11)10-3-4-14-17(5-10)28-9-27-14/h3-7,22H,8-9H2,1-2H3
• InChI Key: VMEJANRODATDOF-UHFFFAOYSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₆O₇
• Molecular Weight: 380.30 g/mol
• Exact Mass: 380.08960285 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 22055-22-7
• 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
• W4PN5LDP26
• MLS000106853
• CHEBI:4645
• NSC-309691
• SMR000111229
• 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benzo[f]isobenzofuran-1-one
• Naphtho(2,3-c)furan-1(3H)-one, 4-hydroxy-6,7-dimethoxy-9-(3,4-(methylenedioxy)phenyl)-
• Naphtho(2,3-c)furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-
• 9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one; NSC 309691
• Naphtho[2,3-c]furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-
• UNII-W4PN5LDP26
• Oprea1_135417
• Oprea1_318204
• CHEMBL221190
• cid_100492
• SCHEMBL1061765
• Diphyllin, >=98% (HPLC)
• BDBM64979
• DTXSID20176534
• HMS1607M09
• HMS2469A22
• NP195
• EX-A3532
• HY-N2532
• XAA05522
• NSC309691
• AKOS000620412
• CCG-111892
• NSC 309691
• AC-34764
• MS-26214
• CS-0022803
• FT-0701233
• E80737
• Q27106426
• 4-Hydroxy-6,7-dimethoxy-9-[3,4-(methylenedioxy)phenyl]-naphtho[2,3-c]furan-1(3H)-one
• 9-(1,3-benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxy-3H-benz[f]isobenzofuran-1-one
• 9-(1,3-BENZODIOXOL-5-YL)-4-HYDROXY-6,7-DIMETHOXYNAPHTHO(2,3-C)FURAN-1(3H)-ONE
• 9-(1,3-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one #
• 9-(1,3-Benzodioxol-5-yl)-6,7-dimethoxy-4-hydroxynaphtho[2,3-c]furan-1(3H)-one
• 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-oxidanyl-3H-benzo[f][2]benzofuran-1-one
• 9-(13-Benzodioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho(2,3-c)furan-1(3H)-one
• 9-(benzo[d][1,3]dioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9886	98.86%
Caco-2	+	0.8169	81.69%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7932	79.32%
OATP2B1 inhibitior	-	0.8709	87.09%
OATP1B1 inhibitior	+	0.9135	91.35%
OATP1B3 inhibitior	+	0.9665	96.65%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8292	82.92%
P-glycoprotein inhibitior	+	0.6041	60.41%
P-glycoprotein substrate	-	0.8638	86.38%
CYP3A4 substrate	+	0.5655	56.55%
CYP2C9 substrate	-	0.8012	80.12%
CYP2D6 substrate	-	0.8332	83.32%
CYP3A4 inhibition	+	0.8578	85.78%
CYP2C9 inhibition	+	0.9389	93.89%
CYP2C19 inhibition	+	0.9332	93.32%
CYP2D6 inhibition	-	0.7537	75.37%
CYP1A2 inhibition	-	0.8550	85.50%
CYP2C8 inhibition	+	0.5407	54.07%
CYP inhibitory promiscuity	+	0.7841	78.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4425	44.25%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.5849	58.49%
Skin irritation	-	0.7847	78.47%
Skin corrosion	-	0.9655	96.55%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5412	54.12%
Micronuclear	+	0.8974	89.74%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7316	73.16%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6150	61.50%
Acute Oral Toxicity (c)	III	0.6180	61.80%
Estrogen receptor binding	+	0.9245	92.45%
Androgen receptor binding	+	0.7264	72.64%
Thyroid receptor binding	+	0.7314	73.14%
Glucocorticoid receptor binding	+	0.9210	92.10%
Aromatase binding	+	0.6016	60.16%
PPAR gamma	+	0.7661	76.61%
Honey bee toxicity	-	0.8691	86.91%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.9563	95.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	31622.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	2238.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	35481.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	10000 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	8912.5 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	99.08%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.23%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.90%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.57%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	94.83%	98.21%
CHEMBL1951	P21397	Monoamine oxidase A	94.48%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.25%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.28%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.20%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.68%	92.62%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.14%	94.80%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.97%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.57%	96.09%
CHEMBL2535	P11166	Glucose transporter	86.82%	98.75%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	85.30%	80.96%
CHEMBL1907	P15144	Aminopeptidase N	83.32%	93.31%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	82.95%	85.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.24%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	81.87%	88.48%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.80%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.42%	99.15%

Plants that contains it

• Arachis hypogaea
• Cleistanthus collinus
• Cleistanthus patulus
• Croton nitens
• Euphorbia franckiana
• Geranium nepalense
• Grindelia ciliata
• Haplophyllum acutifolium
• Haplophyllum alberti-regelii
• Haplophyllum bucharicum
• Haplophyllum cappadocicum
• Haplophyllum dauricum
• Haplophyllum obtusifolium
• Haplophyllum patavinum
• Haplophyllum telephioides
• Haplophyllum tuberculatum
• Haplophyllum vulcanicum
• Hertia intermedia
• Justicia patentiflora
• Justicia procumbens
• Kippistia suaedifolia
• Linum usitatissimum
• Pelargonium reniforme
• Phyllanthus oligospermus
• Podophyllum grayi
• Podophyllum sinense
• Podophyllum versipelle
• Polygala amarella
• Swertia angustifolia
• Swertia paniculata
• Taiwania cryptomerioides

Cross-Links

• PubChem: 100492
• NPASS: NPC22130
• ChEMBL: CHEMBL221190
• LOTUS: LTS0037316
• wikiData: Q105369601