Solasonine

Details

• Internal ID: a06627a7-230c-482f-ac68-843fdb3fac44
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)C)O)O)O)C)C)C)NC1
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C)NC1
• InChI: InChI=1S/C45H73NO16/c1-19-8-13-45(46-16-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(54)34(52)31(49)21(3)56-40)38(33(51)29(18-48)59-42)60-41-37(55)35(53)32(50)28(17-47)58-41/h6,19-21,23-42,46-55H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33+,34-,35+,36-,37-,38+,39-,40+,41+,42-,43+,44+,45-/m1/s1
• InChI Key: QCTMYNGDIBTNSK-XEAAVONHSA-N
• Popularity: 273 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₃NO₁₆
• Molecular Weight: 884.10 g/mol
• Exact Mass: 883.49293524 g/mol
• Topological Polar Surface Area (TPSA): 259.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• 19121-58-5
• Tomatine solaradixine
• Solasonin
• alpha-Solasonine
• UNII-TR60638HXL
• CHEBI:9191
• TR60638HXL
• solanine-S
• .alpha.-Solasonine
• EINECS 242-826-6
• NSC 82149
• beta-D-Galactopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))- (9CI)
• 20318-30-3
• NSC-82149
• C45-H73-N-O16
• PURAPURINE
• SOLASONINE [MI]
• CHEMBL438956
• SCHEMBL2683980
• QCTMYNGDIBTNSK-XEAAVONHSA-N
• DTXSID801028790
• .beta.-D-Galactopyranoside, (3.beta.,22.alpha.,25R)-spirosol-5-en-3-yl O-6-deoxy-.alpha.-L-mannopyranosyl-(1.fwdarw.2)-O-[.beta.-D-glucopyranosyl-(1.fwdarw.3)]-
• .beta.-D-Galactopyranoside, (3.beta.,22.alpha.,25R)-spirosol-5-en-3-yl O-6-deoxy-.alpha.-L-mannopyranosyl-(1?2)-O-[.beta.-D-glucopyranosyl-(1?3)]-
• beta-D-Galactopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))-
• beta-D-Galactopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(12)-O-(beta-D-glucopyranosyl-(13))-
• AKOS030528257
• CCG-270555
• AC-33986
• BS-16392
• S9144
• Q7557107
• (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• .BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-YL O-6- DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1-2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1-3))-
• .BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->3))-
• beta-D-Galactopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8227	82.27%
Caco-2	-	0.8838	88.38%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5883	58.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9003	90.03%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8163	81.63%
P-glycoprotein inhibitior	+	0.7187	71.87%
P-glycoprotein substrate	+	0.5648	56.48%
CYP3A4 substrate	+	0.7396	73.96%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8216	82.16%
CYP3A4 inhibition	-	0.9497	94.97%
CYP2C9 inhibition	-	0.9216	92.16%
CYP2C19 inhibition	-	0.9213	92.13%
CYP2D6 inhibition	-	0.9346	93.46%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7343	73.43%
CYP inhibitory promiscuity	-	0.8790	87.90%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4623	46.23%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9121	91.21%
Skin irritation	-	0.6850	68.50%
Skin corrosion	-	0.9217	92.17%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7678	76.78%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8526	85.26%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8400	84.00%
Acute Oral Toxicity (c)	III	0.6991	69.91%
Estrogen receptor binding	+	0.8503	85.03%
Androgen receptor binding	+	0.6555	65.55%
Thyroid receptor binding	-	0.5622	56.22%
Glucocorticoid receptor binding	-	0.5332	53.32%
Aromatase binding	+	0.6784	67.84%
PPAR gamma	+	0.7321	73.21%
Honey bee toxicity	-	0.6335	63.35%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7285	72.85%

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	99.07%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.54%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.48%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.84%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.84%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.97%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.48%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.09%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.49%	89.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.64%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.45%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.22%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.79%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.93%	98.95%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	82.96%	96.67%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.63%	96.61%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.98%	95.50%
CHEMBL237	P41145	Kappa opioid receptor	81.86%	98.10%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.84%	92.94%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.31%	91.24%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.42%	97.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.31%	94.75%

Plants that contains it

• Achillea millefolium
• Alcea nudiflora
• Alocasia macrorrhizos
• Anaphalis margaritacea
• Angelica sinensis
• Boronia lanceolata
• Campanula pendula
• Carissa spinarum
• Chloranthus holostegius
• Clerodendrum infortunatum
• Corydalis crystallina
• Eucalyptus campanulata
• Euphorbia cattimandoo
• Hemiphragma heterophyllum
• Lasianthus attenuatus var. attenuatus
• Lomandra hastilis
• Mercurialis leiocarpa
• Morisonia scabrida
• Neolitsea sericea
• Ochradenus baccatus
• Plantago ovata
• Podocarpus sellowii
• Podophyllum pleianthum
• Primula denticulata
• Rubus niveus
• Solanum aculeatissimum
• Solanum americanum
• Solanum amygdalifolium
• Solanum anguivi
• Solanum arundo
• Solanum aviculare
• Solanum crinitum
• Solanum dasyphyllum
• Solanum donianum
• Solanum dulcamara
• Solanum linearifolium
• Solanum lycocarpum
• Solanum mammosum
• Solanum melongena
• Solanum myriacanthum
• Solanum nigrum
• Solanum robustum
• Solanum rostratum
• Solanum stoloniferum
• Solanum suaveolens
• Solanum sycophanta
• Spinacia oleracea
• Teucrium cossonii
• Thujopsis dolabrata
• Turnera ulmifolia

Cross-Links

• PubChem: 119247
• NPASS: NPC147753
• LOTUS: LTS0228855
• wikiData: Q7557107