(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-5,5,6a,6b,11,11,14b-heptamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4,4a,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: 32a9e494-5b49-4f9b-b2e3-160e855ad937
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-5,5,6a,6b,11,11,14b-heptamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4,4a,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(CC5C(CC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)O)O)C)CO)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC([C@@H]5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O)C)(C)C)C)C)O)CO)(C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C51H78O17/c1-12-24(3)42(61)67-39-40(68-43(62)25(4)13-2)51(23-52)28(19-46(39,5)6)27-14-15-30-48(9)17-16-26(18-31(48)47(7,8)22-50(30,11)49(27,10)20-32(51)54)64-45-36(58)37(35(57)38(66-45)41(59)60)65-44-34(56)33(55)29(53)21-63-44/h12-14,26,28-40,44-45,52-58H,15-23H2,1-11H3,(H,59,60)/b24-12-,25-13-/t26-,28-,29-,30+,31+,32+,33-,34+,35-,36+,37-,38-,39-,40-,44-,45+,48+,49+,50+,51-/m0/s1
• InChI Key: ROAOAOLBVDEIGY-HPWXLPQGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₇₈O₁₇
• Molecular Weight: 963.20 g/mol
• Exact Mass: 962.52390102 g/mol
• Topological Polar Surface Area (TPSA): 268.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 3.47
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8667	86.67%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8287	82.87%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9407	94.07%
P-glycoprotein inhibitior	+	0.7533	75.33%
P-glycoprotein substrate	+	0.6213	62.13%
CYP3A4 substrate	+	0.7369	73.69%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8966	89.66%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7535	75.35%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.6848	68.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.6942	69.42%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6575	65.75%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.6010	60.10%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7648	76.48%
Androgen receptor binding	+	0.7512	75.12%
Thyroid receptor binding	+	0.5806	58.06%
Glucocorticoid receptor binding	+	0.7966	79.66%
Aromatase binding	+	0.6213	62.13%
PPAR gamma	+	0.8202	82.02%
Honey bee toxicity	-	0.6817	68.17%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9585	95.85%

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	99.05%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.90%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.64%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.49%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.72%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.31%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.12%	91.07%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.53%	95.50%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	86.20%	91.65%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.62%	89.67%
CHEMBL226	P30542	Adenosine A1 receptor	85.37%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.22%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.88%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.78%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.45%	89.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.96%	96.90%
CHEMBL5028	O14672	ADAM10	83.53%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.48%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.34%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.37%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.25%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.20%	95.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.53%	89.34%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.45%	100.00%

Plants that contains it

• Polyspora chrysandra

Cross-Links

• PubChem: 163000188
• LOTUS: LTS0213414
• wikiData: Q105242006