Visnadine

Details

• Internal ID: f8464cb4-c14f-4616-9661-e9f646632c9f
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: [(9R,10R)-10-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C2=C(C=CC3=C2OC(=O)C=C3)OC1(C)C)OC(=O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]1[C@@H](C2=C(C=CC3=C2OC(=O)C=C3)OC1(C)C)OC(=O)C
• InChI: InChI=1S/C21H24O7/c1-6-11(2)20(24)27-19-18(25-12(3)22)16-14(28-21(19,4)5)9-7-13-8-10-15(23)26-17(13)16/h7-11,18-19H,6H2,1-5H3/t11-,18-,19-/m1/s1
• InChI Key: GVBNSPFBYXGREE-CXWAGAITSA-N
• Popularity: 86 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.15220310 g/mol
• Topological Polar Surface Area (TPSA): 88.10 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.53
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• Visnadin
• Carduben
• Cardine
• Visnadina
• Visnadinum
• Selva
• Carduben-S
• 477-32-7
• Visnadine (INN)
• UNII-0RL4V0K263
• 0RL4V0K263
• EINECS 207-515-1
• BRN 0055264
• visnacorin
• visnamine
• 5-19-06-00272 (Beilstein Handbook Reference)
• Visnadina [DCIT]
• 3-(alpha-Methylbutyryloxy)-4-acetoxy-3,4-dihydroseseline
• Visnadine [INN:BAN]
• VISNADINE [INN]
• (alpha-Methylbutyryloxy)-3'-acetoxy-4'-dihydro-3',4'-seselin
• Visnadinum [INN-Latin]
• VISNADINE (MART.)
• VISNADINE [MART.]
• C09316
• D08735
• 3,4,5-Trihydroxy-2,2-dimethyl-6-chromanacrylic acid delta-lactone 4-acetate 3-(2-methylbutyrate)
• 3,4,5-TRIHYDROXY-2,2-DIMETHYL-6-CHROMANACRYLIC ACID D-LACTONE 4-ACETATE 3-(2-METHYLBUTYRATE).
• Butyric acid, 2-methyl-, 9-ester with 9,10-dihydro-9,10-dihydroxy-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-2-one-acetate
• Visnadine [BAN:INN]
• AC1L9CC8
• C21H24O7
• (alpha-Methylbutyryloxy)-3'-acetoxy-4'-dihydro-3',4'-seselin [German]
• VISNADINE [MI]
• VISNADINE [INCI]
• VISNADINE [WHO-DD]
• SCHEMBL309874
• CHEMBL3989444
• CHEBI:10001
• C04AX24
• DTXSID301023583
• ZINC00608130
• Visnadine, >=95% (LC/MS-ELSD)
• DB13355
• [(9R,10R)-10-acetoxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] (2R)-2-methylbutanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9762	97.62%
Caco-2	+	0.6626	66.26%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6175	61.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9140	91.40%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9406	94.06%
P-glycoprotein inhibitior	+	0.8527	85.27%
P-glycoprotein substrate	-	0.7222	72.22%
CYP3A4 substrate	+	0.5672	56.72%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.8398	83.98%
CYP3A4 inhibition	-	0.7073	70.73%
CYP2C9 inhibition	-	0.5931	59.31%
CYP2C19 inhibition	-	0.6430	64.30%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.5172	51.72%
CYP2C8 inhibition	+	0.4534	45.34%
CYP inhibitory promiscuity	-	0.6447	64.47%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5592	55.92%
Eye corrosion	-	0.9846	98.46%
Eye irritation	-	0.9096	90.96%
Skin irritation	-	0.8416	84.16%
Skin corrosion	-	0.9531	95.31%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6934	69.34%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.6072	60.72%
skin sensitisation	-	0.8166	81.66%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6024	60.24%
Acute Oral Toxicity (c)	III	0.7684	76.84%
Estrogen receptor binding	+	0.6970	69.70%
Androgen receptor binding	+	0.7296	72.96%
Thyroid receptor binding	-	0.5271	52.71%
Glucocorticoid receptor binding	+	0.7653	76.53%
Aromatase binding	-	0.5955	59.55%
PPAR gamma	+	0.5879	58.79%
Honey bee toxicity	-	0.7913	79.13%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.80%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.22%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.77%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.93%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	92.39%	83.82%
CHEMBL2996	Q05655	Protein kinase C delta	88.04%	97.79%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.75%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.14%	92.62%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.13%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.56%	99.23%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	81.92%	92.26%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.81%	85.30%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.79%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.02%	96.95%

Plants that contains it

• Ferula xeromorpha
• Ferulopsis hystrix
• Ligusticum lucidum
• Peucedanum japonicum
• Phlojodicarpus sibiricus
• Visnaga daucoides

Cross-Links

• PubChem: 442151
• NPASS: NPC288372
• LOTUS: LTS0116453
• wikiData: Q15410171