Spiro(7H-indeno(4,5-d)-1,3-dioxole-7,1'(2'H)-isoquinolin)-8(6H)-one,7'-(beta-D-glucopyranosyloxy)-3',4'-dihydro-6'-methoxy-2'-methyl-, (2'S)-

Details

• Internal ID: b766977c-c4b8-41ff-a2f3-113edce41e48
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (1S)-6-methoxy-2-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,4-dihydroisoquinoline-1,7'-6H-cyclopenta[g][1,3]benzodioxole]-8'-one
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C13CC4=C(C3=O)C5=C(C=C4)OCO5)OC6C(C(C(C(O6)CO)O)O)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2[C@]13CC4=C(C3=O)C5=C(C=C4)OCO5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)OC
• InChI: InChI=1S/C26H29NO10/c1-27-6-5-12-7-16(33-2)17(36-25-22(31)21(30)20(29)18(10-28)37-25)8-14(12)26(27)9-13-3-4-15-23(35-11-34-15)19(13)24(26)32/h3-4,7-8,18,20-22,25,28-31H,5-6,9-11H2,1-2H3/t18-,20-,21+,22-,25-,26+/m1/s1
• InChI Key: IFLZXNCKAOBSFX-HNYHEDDASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₉NO₁₀
• Molecular Weight: 515.50 g/mol
• Exact Mass: 515.17914612 g/mol
• Topological Polar Surface Area (TPSA): 147.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): -0.28
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• Spiro(7H-indeno(4,5-d)-1,3-dioxole-7,1'(2'H)-isoquinolin)-8(6H)-one,7'-(beta-D-glucopyranosyloxy)-3',4'-dihydro-6'-methoxy-2'-methyl-, (2'S)-
• Parviflorine
• DTXSID00226869

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5724	57.24%
Caco-2	-	0.7296	72.96%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Lysosomes	0.4067	40.67%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8810	88.10%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8139	81.39%
P-glycoprotein inhibitior	+	0.6279	62.79%
P-glycoprotein substrate	-	0.5401	54.01%
CYP3A4 substrate	+	0.6762	67.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7502	75.02%
CYP3A4 inhibition	-	0.8883	88.83%
CYP2C9 inhibition	-	0.8677	86.77%
CYP2C19 inhibition	-	0.8299	82.99%
CYP2D6 inhibition	-	0.8153	81.53%
CYP1A2 inhibition	-	0.9236	92.36%
CYP2C8 inhibition	-	0.7640	76.40%
CYP inhibitory promiscuity	-	0.8678	86.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6121	61.21%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9414	94.14%
Skin irritation	-	0.7891	78.91%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3809	38.09%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8578	85.78%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7817	78.17%
Acute Oral Toxicity (c)	III	0.6458	64.58%
Estrogen receptor binding	+	0.7899	78.99%
Androgen receptor binding	+	0.6582	65.82%
Thyroid receptor binding	-	0.6157	61.57%
Glucocorticoid receptor binding	+	0.6486	64.86%
Aromatase binding	+	0.5420	54.20%
PPAR gamma	+	0.6447	64.47%
Honey bee toxicity	-	0.7241	72.41%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8224	82.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.36%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.90%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.67%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.63%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.54%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.74%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.47%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.07%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.35%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.72%	95.89%
CHEMBL4208	P20618	Proteasome component C5	90.68%	90.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.51%	82.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.45%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.31%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.12%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.78%	97.09%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.28%	82.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.89%	100.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.58%	97.50%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.34%	90.95%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.15%	92.38%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.75%	97.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.05%	92.94%

Plants that contains it

• Fumaria parviflora

Cross-Links

• PubChem: 156800
• LOTUS: LTS0050013
• wikiData: Q83106440