Visnagin

Details

• Internal ID: 2e7d533b-60a7-4553-8dae-0efd854e3bcc
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones > Furanochromones
• IUPAC Name: 4-methoxy-7-methylfuro[3,2-g]chromen-5-one
• SMILES (Canonical): CC1=CC(=O)C2=C(O1)C=C3C(=C2OC)C=CO3
• SMILES (Isomeric): CC1=CC(=O)C2=C(O1)C=C3C(=C2OC)C=CO3
• InChI: InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3
• InChI Key: NZVQLVGOZRELTG-UHFFFAOYSA-N
• Popularity: 241 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₀O₄
• Molecular Weight: 230.22 g/mol
• Exact Mass: 230.05790880 g/mol
• Topological Polar Surface Area (TPSA): 48.70 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.86
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 82-57-5
• Desmethoxykhellin
• Visnagidin
• Visnagine
• 4-Methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one
• 5-Methoxy-2-methylfuranochromone
• 4-methoxy-7-methylfuro[3,2-g]chromen-5-one
• 4-Methoxy-7-methyl-furo[3,2-g]chromen-5-one
• C13H10O4
• EINECS 201-430-3
• NSC 100593
• BRN 0234955
• UNII-P64438MLBW
• CHEMBL45176
• P64438MLBW
• CHEBI:10002
• NSC-100593
• 4-Methoxy-7-methyl-5H-furo(3,2-g)(1)-benzopyran-5-one
• 5H-Furo[3,2-g][1]benzopyran-5-one, 4-methoxy-7-methyl-
• 5H-FURO(3,2-g)(1)BENZOPYRAN-5-ONE, 4-METHOXY-7-METHYL-
• 4-Methoxy-7-methylfuro(3,2-g)chromen-5-one
• 5-19-06-00030 (Beilstein Handbook Reference)
• Desmethoxykhellin; NSC 100593; Visnagidin; Visnagine
• SR-01000765669
• 4-Methoxy-7-methyl-5H-furo[3,2-g][1]benZopyran-5-one
• 4-METHOXY-7-METHYL-5H-FURO(3,2-G)(1)BENZOPYRAN-5-ONE
• 5H-Furo[3,2-g][1]benzopyran-5-one,4-methoxy-7-methyl-
• Spectrum_001227
• SpecPlus_000453
• VISNAGIN [MI]
• Spectrum2_001796
• Spectrum3_001340
• Spectrum4_001766
• Spectrum5_000351
• D0MH4R
• Oprea1_854963
• BSPBio_003099
• GTPL433
• KBioGR_002251
• KBioSS_001707
• SPECTRUM310041
• MLS000697721
• DivK1c_006549
• SCHEMBL498450
• SPBio_001751
• MEGxp0_000332
• KBio1_001493
• KBio2_001707
• KBio2_004275
• KBio2_006843
• KBio3_002319
• NZVQLVGOZRELTG-UHFFFAOYSA-
• DTXSID50231509
• FUK-724
• HMS2268P15
• HY-N1082
• 5H-Furo[3, 4-methoxy-7-methyl-
• BBL027492
• BDBM50051349
• CCG-38444
• LMPK13110003
• MFCD00005008
• NSC100593
• STL372894
• AKOS015955735
• SDCCGMLS-0066603.P001
• NCGC00095626-01
• NCGC00095626-02
• NCGC00178297-01
• LS-70733
• SMR000112234
• VS-08551
• 4-methoxy-7-methylfuro[3,2-g]chromen-5-on
• CS-0016370
• FT-0603293
• C09049
• EN300-6745554
• L000822
• 4-methoxy-7-methylpyrano[3,2-f][1]benzoxol-5-one
• Q7936365
• SR-01000765669-3
• SR-01000765669-4
• 4-Methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one #
• BRD-K68995359-001-02-8
• BRD-K68995359-001-06-9
• 4-Methoxy-7-methyl-5H-furo-nu[3,2-g][1]benzopyran-5-one
• 4-Methoxy-7-methyl-5H-furo[3,2-g]-1-benzopyran-5-one
• InChI=1/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	+	0.8196	81.96%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6842	68.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9657	96.57%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8589	85.89%
P-glycoprotein inhibitior	-	0.8365	83.65%
P-glycoprotein substrate	-	0.8507	85.07%
CYP3A4 substrate	-	0.5332	53.32%
CYP2C9 substrate	-	0.8494	84.94%
CYP2D6 substrate	-	0.8309	83.09%
CYP3A4 inhibition	+	0.8766	87.66%
CYP2C9 inhibition	+	0.6665	66.65%
CYP2C19 inhibition	+	0.9436	94.36%
CYP2D6 inhibition	+	0.9077	90.77%
CYP1A2 inhibition	+	0.9776	97.76%
CYP2C8 inhibition	-	0.7690	76.90%
CYP inhibitory promiscuity	+	0.8240	82.40%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.3970	39.70%
Eye corrosion	-	0.9194	91.94%
Eye irritation	+	0.6647	66.47%
Skin irritation	-	0.6666	66.66%
Skin corrosion	-	0.9852	98.52%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6425	64.25%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8580	85.80%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.8047	80.47%
Acute Oral Toxicity (c)	III	0.7800	78.00%
Estrogen receptor binding	+	0.7334	73.34%
Androgen receptor binding	+	0.7881	78.81%
Thyroid receptor binding	-	0.4940	49.40%
Glucocorticoid receptor binding	+	0.5804	58.04%
Aromatase binding	+	0.7930	79.30%
PPAR gamma	+	0.6204	62.04%
Honey bee toxicity	-	0.8885	88.85%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8259	82.59%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	1995.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.20%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.80%	91.11%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	91.40%	94.03%
CHEMBL3401	O75469	Pregnane X receptor	91.13%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	90.81%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.17%	95.56%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	89.64%	93.65%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.24%	85.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.58%	93.99%
CHEMBL2581	P07339	Cathepsin D	86.45%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.49%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.48%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.71%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.48%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.43%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	82.19%	94.75%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.32%	96.67%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	81.18%	85.00%

Plants that contains it

• Actaea dahurica
• Musineon divaricatum
• Visnaga daucoides

Cross-Links

• PubChem: 6716
• NPASS: NPC190572
• ChEMBL: CHEMBL45176
• LOTUS: LTS0003546
• wikiData: Q7936365