Cyaonoside B

Details

• Internal ID: 1ffc612b-0702-4073-a0c3-0defcb5d7ed9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)C(=O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2O)O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)C)C(=O)O)O)O)O)O
• InChI: InChI=1S/C48H76O18/c1-21-28(50)30(52)32(54)39(61-21)64-36-34(56)37(38(58)59)65-41(35(36)57)63-27-12-13-45(6)25(44(27,4)5)11-14-47(8)26(45)10-9-22-23-19-43(2,3)15-17-48(23,18-16-46(22,47)7)42(60)66-40-33(55)31(53)29(51)24(20-49)62-40/h9,21,23-37,39-41,49-57H,10-20H2,1-8H3,(H,58,59)/t21-,23-,24+,25-,26+,27-,28-,29+,30+,31-,32+,33+,34-,35+,36-,37-,39-,40-,41+,45-,46+,47+,48-/m0/s1
• InChI Key: LBHYRBPEXITYTN-WYPLEBMUSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₆O₁₈
• Molecular Weight: 941.10 g/mol
• Exact Mass: 940.50316557 g/mol
• Topological Polar Surface Area (TPSA): 292.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• 51161-58-1
• PUTRANOSIDE C
• CHEMBL2047216
• LBHYRBPEXITYTN-WYPLEBMUSA-N
• HY-N9522
• MS-31753
• PD166567
• CS-0198369
• E88608
• (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
• beta-D-glucopyranosyl-[alpha-L-rhamnopyranosyl-(1-->3)-betaD-glucuronopyranosyl-(1-->3)]-3beta-hydroxyolean-12-ene28-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7941	79.41%
Caco-2	-	0.8830	88.30%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8948	89.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7110	71.10%
OATP1B3 inhibitior	-	0.5056	50.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6474	64.74%
BSEP inhibitior	+	0.7731	77.31%
P-glycoprotein inhibitior	+	0.7562	75.62%
P-glycoprotein substrate	-	0.7672	76.72%
CYP3A4 substrate	+	0.7159	71.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.8459	84.59%
CYP2C9 inhibition	-	0.8380	83.80%
CYP2C19 inhibition	-	0.9220	92.20%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.8499	84.99%
CYP2C8 inhibition	+	0.7314	73.14%
CYP inhibitory promiscuity	-	0.9381	93.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6298	62.98%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9043	90.43%
Skin irritation	-	0.5723	57.23%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6727	67.27%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.9697	96.97%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.9442	94.42%
Acute Oral Toxicity (c)	III	0.7628	76.28%
Estrogen receptor binding	+	0.7651	76.51%
Androgen receptor binding	+	0.7291	72.91%
Thyroid receptor binding	-	0.5475	54.75%
Glucocorticoid receptor binding	+	0.7733	77.33%
Aromatase binding	+	0.6135	61.35%
PPAR gamma	+	0.7993	79.93%
Honey bee toxicity	-	0.6855	68.55%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	+	0.9778	97.78%

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	98.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.72%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.08%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.76%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.63%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.00%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.44%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.14%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.42%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.51%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.49%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.35%	93.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.39%	92.50%

Plants that contains it

• Bobgunnia madagascariensis
• Diospyros zombensis
• Dumasia truncata
• Swartzia simplex

Cross-Links

• PubChem: 21635581
• LOTUS: LTS0038882
• wikiData: Q105149302