Nocturnoside A

Details

• Internal ID: db60ce71-71a2-41b6-b4c6-b28849f3d12c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(4S,5'R,7S,8R,9S,13R)-15-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]-4,6-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxyoxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CC(C(C6)C7(C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)OC2C(C(C(CO2)O)O)O)OC2C(C(C(C(O2)CO)O)O)O)O)C)C)C)OC1
• SMILES (Isomeric): C[C@@H]1CCC2([C@H]([C@H]3[C@@H](O2)CC4[C@@]3(CCC5C4CC=C6[C@@]5(CC(C(C6)[C@@]7([C@@H]([C@H]([C@H]([C@H](O7)CO)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)CO)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)C)C)C)OC1
• InChI: InChI=1S/C56H90O28/c1-20-7-10-55(75-18-20)21(2)34-29(82-55)12-25-23-6-5-22-11-26(27(61)13-54(22,4)24(23)8-9-53(25,34)3)56(84-52-45(73)41(69)38(66)32(16-59)78-52)48(81-49-42(70)35(63)28(62)19-74-49)47(80-51-44(72)40(68)37(65)31(15-58)77-51)46(33(17-60)83-56)79-50-43(71)39(67)36(64)30(14-57)76-50/h5,20-21,23-52,57-73H,6-19H2,1-4H3/t20-,21+,23?,24?,25?,26?,27?,28-,29+,30-,31-,32-,33-,34+,35+,36-,37-,38-,39+,40+,41+,42-,43-,44-,45-,46+,47+,48-,49+,50+,51+,52+,53+,54+,55?,56+/m1/s1
• InChI Key: HXWQHQCQOBWGDB-VDYHUCKYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₉₀O₂₈
• Molecular Weight: 1211.30 g/mol
• Exact Mass: 1210.56186221 g/mol
• Topological Polar Surface Area (TPSA): 445.00 Ų
• XlogP: -4.30
• Atomic LogP (AlogP): -5.96
• H-Bond Acceptor: 28
• H-Bond Donor: 17
• Rotatable Bonds: 13

Synonyms

• 137318-80-0
• 3-O-(beta-D-Glucopyranosyl(1-3)-beta-D-glucopyranosyl(1-2)-beta-D-glucopyranosyl((3-1)-beta D-xylopyranosyl)(1-4)-beta-D-galactopyranosyl)(25R)-spirost-5-ene-2alpha,3beta-diol
• beta-D-Galactopyranoside, (2alpha,3beta,25R)-2-hydroxyspirost-5-en-3-yl O-beta-D-glucopyranosyl-(1-3)-O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8128	81.28%
Caco-2	-	0.8831	88.31%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7775	77.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8643	86.43%
OATP1B3 inhibitior	+	0.9226	92.26%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8545	85.45%
P-glycoprotein inhibitior	+	0.7372	73.72%
P-glycoprotein substrate	+	0.6297	62.97%
CYP3A4 substrate	+	0.7501	75.01%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8216	82.16%
CYP3A4 inhibition	-	0.9129	91.29%
CYP2C9 inhibition	-	0.9142	91.42%
CYP2C19 inhibition	-	0.9228	92.28%
CYP2D6 inhibition	-	0.9336	93.36%
CYP1A2 inhibition	-	0.9164	91.64%
CYP2C8 inhibition	+	0.8054	80.54%
CYP inhibitory promiscuity	-	0.9048	90.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5234	52.34%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9044	90.44%
Skin irritation	-	0.5501	55.01%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	-	0.8170	81.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7747	77.47%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.9238	92.38%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7332	73.32%
Acute Oral Toxicity (c)	I	0.7663	76.63%
Estrogen receptor binding	+	0.8335	83.35%
Androgen receptor binding	+	0.7619	76.19%
Thyroid receptor binding	-	0.5246	52.46%
Glucocorticoid receptor binding	+	0.5934	59.34%
Aromatase binding	+	0.6341	63.41%
PPAR gamma	+	0.7750	77.50%
Honey bee toxicity	-	0.5638	56.38%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9341	93.41%

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	98.72%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	98.02%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.94%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.23%	91.11%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	95.80%	87.16%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.90%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.61%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	92.10%	95.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.89%	95.89%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	88.81%	95.58%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.65%	97.53%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.58%	97.25%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.42%	91.24%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.35%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	88.15%	92.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.69%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.38%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.90%	86.33%
CHEMBL237	P41145	Kappa opioid receptor	85.88%	98.10%
CHEMBL3401	O75469	Pregnane X receptor	85.52%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.02%	94.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.08%	89.05%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.63%	92.94%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.07%	95.83%
CHEMBL5028	O14672	ADAM10	80.92%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.65%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.29%	93.00%

Plants that contains it

• Cestrum nocturnum

Cross-Links

• PubChem: 195840
• LOTUS: LTS0052282
• wikiData: Q105035178