Sitoindoside I

Details

• Internal ID: 4bdd517e-67df-401f-973b-66c5b3860697
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl hexadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)OCC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(C4CC=C3C2)CCC5C(C)CCC(CC)C(C)C)C)C)O)O)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@]5([C@H]([C@@H]4CC=C3C2)CC[C@@H]5[C@H](C)CC[C@@H](CC)C(C)C)C)C)O)O)O
• InChI: InChI=1S/C51H90O7/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-45(52)56-34-44-46(53)47(54)48(55)49(58-44)57-39-29-31-50(6)38(33-39)25-26-40-42-28-27-41(51(42,7)32-30-43(40)50)36(5)23-24-37(9-2)35(3)4/h25,35-37,39-44,46-49,53-55H,8-24,26-34H2,1-7H3/t36-,37-,39+,40+,41-,42+,43+,44-,46-,47+,48-,49-,50+,51-/m1/s1
• InChI Key: JCLYMCVRBRHEHI-TWDDPRSNSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₉₀O₇
• Molecular Weight: 815.30 g/mol
• Exact Mass: 814.66865521 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 15.10
• Atomic LogP (AlogP): 11.88
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 24

Synonyms

• 18749-71-8
• (3beta)-Stigmast-5-en-3-yl 6-O-palmitoyl-beta-D-glucopyranoside
• Esterified Steryl Glucosides
• ASGlu
• Longiside B;Sitoindoside;Daucosterol 6'-O-palmitate
• CHEMBL4452244
• CHEBI:67595
• DTXSID301317443
• [(2R,3S,4S,5R,6R)-6-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl hexadecanoate
• AKOS032962079
• LS-146751
• Q27136065
• beta-sitosteryl-3-O-beta-D-glucopyranosyl-6'-O-palmitate
• 6'-(beta-sitosteryl-3-O-beta-D-glucopyranosidyl)hexadecanoate
• (3beta)-stigmast-5-en-3-yl 6-O-hexadecanoyl-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9450	94.50%
Caco-2	-	0.8607	86.07%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8291	82.91%
OATP2B1 inhibitior	-	0.5856	58.56%
OATP1B1 inhibitior	+	0.8703	87.03%
OATP1B3 inhibitior	+	0.8305	83.05%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7026	70.26%
BSEP inhibitior	+	0.8762	87.62%
P-glycoprotein inhibitior	+	0.7355	73.55%
P-glycoprotein substrate	+	0.6756	67.56%
CYP3A4 substrate	+	0.7553	75.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8832	88.32%
CYP3A4 inhibition	-	0.8585	85.85%
CYP2C9 inhibition	-	0.7605	76.05%
CYP2C19 inhibition	-	0.8202	82.02%
CYP2D6 inhibition	-	0.9138	91.38%
CYP1A2 inhibition	-	0.7844	78.44%
CYP2C8 inhibition	+	0.6788	67.88%
CYP inhibitory promiscuity	-	0.7486	74.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6813	68.13%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9066	90.66%
Skin irritation	+	0.4939	49.39%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3829	38.29%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6887	68.87%
skin sensitisation	-	0.8841	88.41%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9215	92.15%
Acute Oral Toxicity (c)	III	0.6283	62.83%
Estrogen receptor binding	+	0.8290	82.90%
Androgen receptor binding	+	0.7268	72.68%
Thyroid receptor binding	-	0.6122	61.22%
Glucocorticoid receptor binding	+	0.5591	55.91%
Aromatase binding	+	0.5815	58.15%
PPAR gamma	+	0.6477	64.77%
Honey bee toxicity	-	0.7664	76.64%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6873	68.73%
Fish aquatic toxicity	+	0.9912	99.12%

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	98.99%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.48%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.39%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.68%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.53%	94.45%
CHEMBL220	P22303	Acetylcholinesterase	96.65%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.81%	99.17%
CHEMBL240	Q12809	HERG	95.05%	89.76%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.96%	93.56%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	94.38%	85.94%
CHEMBL5255	O00206	Toll-like receptor 4	94.28%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	93.58%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.18%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.78%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.62%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.33%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.34%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.40%	86.33%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	87.76%	92.86%
CHEMBL1871	P10275	Androgen Receptor	87.42%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.41%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.27%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.23%	89.05%
CHEMBL299	P17252	Protein kinase C alpha	84.29%	98.03%
CHEMBL2996	Q05655	Protein kinase C delta	83.98%	97.79%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.95%	85.31%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.89%	96.47%
CHEMBL5028	O14672	ADAM10	82.66%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	82.42%	95.93%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.16%	95.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.56%	89.62%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.12%	97.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.05%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	80.95%	94.73%

Plants that contains it

• Ajuga australis
• Alnus cordata
• Aloe deltoideodonta
• Aloe microstigma
• Alpinia officinarum
• Alstonia angustiloba
• Amphiachyris dracunculoides
• Annona cherimola
• Antennaria geyeri
• Baccharis grandicapitulata
• Bauhinia purpurea
• Beesia calthifolia
• Boschniakia rossica
• Botrychium ternatum
• Bursera kerberi
• Capsicum annuum
• Centaurea regia
• Chrozophora plicata
• Clerodendrum trichotomum
• Clinacanthus nutans
• Crinum latifolium
• Crotalaria stolzii
• Curcuma aeruginosa
• Delphinium giraldii
• Dracaena draco
• Elaeagnus pungens
• Eriosema chinense
• Eucalyptus albens
• Euonymus fortunei
• Euphorbia guyoniana
• Euploca racemosa
• Ficus carica
• Gyrinops walla
• Hedysarum gmelinii
• Helenium integrifolium
• Hemionitis aschenborniana
• Incarvillea delavayi
• Juniperus scopulorum
• Lasianthaea podocephala
• Leitneria floridana
• Ligularia dolichobotrys
• Lupinus cosentinii
• Maquira coriacea
• Melampodium leucanthum
• Mentha longifolia
• Musa × paradisiaca
• Myrica pensylvanica
• Myrtopsis sellingii
• Neopallasia pectinata
• Papaver pseudocanescens
• Papaver somniferum
• Pellacalyx axillaris
• Peperomia filiformis
• Phlomis crinita
• Plumbago zeylanica
• Psidium acutangulum
• Pyrolirion flavum
• Renealmia alpinia
• Rhododendron micranthum
• Rhododendron mucronulatum
• Salvia aegyptiaca
• Seseli libanotis
• Sideritis dasygnaphala
• Solanum americanum
• Stellaria media
• Strychnos cathayensis
• Tephroseris kirilowii
• Tephroseris palustris
• Thermopsis mollis
• Trichocolea tomentella
• Woodwardia orientalis

Cross-Links

• PubChem: 9832350
• NPASS: NPC209177
• LOTUS: LTS0071215
• wikiData: Q27136065