Picroside Ii

Details

• Internal ID: 84d04390-2507-4d05-8f5c-944671167847
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxy-3-methoxybenzoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C(=O)O[C@H]2[C@@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C23H28O13/c1-31-12-6-9(2-3-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3/t10-,13-,14-,15-,16+,17-,18+,19+,21+,22+,23-/m1/s1
• InChI Key: AKNILCMFRRDTEY-NUGKWEEESA-N
• Popularity: 189 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₁₃
• Molecular Weight: 512.50 g/mol
• Exact Mass: 512.15299094 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.01
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 39012-20-9
• Vanilloyl catalpol
• 6-Vanilloylcatalpol
• Ampicoside
• XX0PFP9RVI
• DTXSID30904845
• 1961245-47-5
• [(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxy-3-methoxybenzoate
• (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-((4-hydroxy-3-methoxybenzoyl)oxy)-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-C)pyran-2-yl beta-D-glucopyranoside
• beta-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-((4-hydroxy-3-methoxybenzoyl)oxy)-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-C)pyran-2-yl
• beta-D-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-((4-hydroxy-3-methoxybenzoyl)oxy)-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl, (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-
• ((1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3,9-dioxatricyclo(4.4.0.02,4)dec-7-en-5-yl) 4-hydroxy-3-methoxybenzoate
• RefChem:174197
• DTXCID601333961
• ((1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,5a,6,6a-tetrahydro-1bH-oxireno(5,6)cyclopenta(1,3-c)pyran-6-yl) 4-hydroxy-3-methoxybenzoate
• 254-247-6
• (1AS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-6-yl 4-hydroxy-3-methoxybenzoate
• C23H28O13
• MFCD00135962
• EINECS 254-247-6
• UNII-XX0PFP9RVI
• Picroside II (Standard)
• CHEMBL510404
• MEGxp0_001244
• SCHEMBL29425971
• SCHEMBL30387354
• ACon1_001520
• HY-N0408R
• HMS6018H20
• HY-N0408
• s3765
• AKOS037514782
• CCG-269786
• NCGC00180420-01
• NCGC00180420-03
• NCGC00180420-04
• CS-0008940
• F869650
• BRD-K40184968-001-01-7
• (1AS,1BS,2S,5AR,6S,6AS)-1A,1B,2,5A,6,6A-HEXAHYDRO-6-((4-HYDROXY-3-METHOXYBENZOYL)OXY)-1A-(HYDROXYMETHYL)OXIRENO(4,5)CYCLOPENTA(1,2-C)PYRAN-2-YL .BETA.-D-GLUCOPYRANOSIDE
• (1aS,1bS,2S,5aR,6S,6aS)-1A-(Hydroxymethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2-Yl)Oxy)-1A,1B,2,5A,6,6A-Hexahydrooxireno[2',3':4,5]Cyclopenta[1,2-C]Pyran-6-Yl4-Hydroxy-3-Methoxybenzoate
• .BETA.-D-GLUCOPYRANOSIDE, (1AS,1BS,2S,5AR,6S,6AS)-1A,1B,2,5A,6,6A-HEXAHYDRO-6-((4-HYDROXY-3-METHOXYBENZOYL)OXY)-1A-(HYDROXYMETHYL)OXIRENO(4,5)CYCLOPENTA(1,2-C)PYRAN-2-YL
• .BETA.-D-GLUCOPYRANOSIDE, 1A,1B,2,5A,6,6A-HEXAHYDRO-6-((4-HYDROXY-3-METHOXYBENZOYL)OXY)-1A-(HYDROXYMETHYL)OXIRENO(4,5)CYCLOPENTA(1,2-C)PYRAN-2-YL, (1AS-(1A.ALPHA.,1B.BETA.,2.BETA.,5A.BETA.,6.BETA.,6A.ALPHA.))-
• [(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 4-hydroxy-3-methoxy-benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6435	64.35%
Caco-2	-	0.9039	90.39%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5653	56.53%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8002	80.02%
OATP1B3 inhibitior	+	0.9676	96.76%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6085	60.85%
P-glycoprotein inhibitior	-	0.6142	61.42%
P-glycoprotein substrate	-	0.5743	57.43%
CYP3A4 substrate	+	0.6735	67.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8451	84.51%
CYP3A4 inhibition	-	0.8901	89.01%
CYP2C9 inhibition	-	0.8604	86.04%
CYP2C19 inhibition	-	0.7030	70.30%
CYP2D6 inhibition	-	0.8722	87.22%
CYP1A2 inhibition	-	0.8509	85.09%
CYP2C8 inhibition	+	0.6909	69.09%
CYP inhibitory promiscuity	-	0.7046	70.46%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5543	55.43%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9328	93.28%
Skin irritation	-	0.7812	78.12%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5132	51.32%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7891	78.91%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6386	63.86%
Acute Oral Toxicity (c)	III	0.5594	55.94%
Estrogen receptor binding	+	0.7762	77.62%
Androgen receptor binding	-	0.5194	51.94%
Thyroid receptor binding	+	0.5635	56.35%
Glucocorticoid receptor binding	+	0.6293	62.93%
Aromatase binding	+	0.5701	57.01%
PPAR gamma	+	0.6973	69.73%
Honey bee toxicity	-	0.8000	80.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7049	70.49%
Fish aquatic toxicity	+	0.6878	68.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.17%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.17%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.92%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.85%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.83%	96.21%
CHEMBL4208	P20618	Proteasome component C5	92.58%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.29%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.81%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.74%	89.00%
CHEMBL3194	P02766	Transthyretin	88.30%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.85%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.49%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.29%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.54%	96.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.14%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.75%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	84.32%	91.49%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.84%	96.90%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.71%	96.61%
CHEMBL5255	O00206	Toll-like receptor 4	80.73%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.29%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.25%	92.62%

Plants that contains it

• Catalpa ovata
• Garcinia subelliptica
• Juncus effusus
• Kandelia candel
• Myroxylon peruiferum
• Neopicrorhiza scrophulariiflora
• Veronica alpina
• Veronica anagallis-aquatica
• Veronica cymbalaria
• Veronica hederifolia
• Veronica thomsonii
• Veronica turrilliana

Cross-Links

• PubChem: 11944602
• NPASS: NPC130730
• LOTUS: LTS0117232
• wikiData: Q72499475