(2S,3S,4S,5R,6R)-6-[[(3S,4aS,5S,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8-dihydroxy-8a-(hydroxymethyl)-5-methoxycarbonyl-5,6a,6b,11,11,14b-hexamethyl-9-[(2R)-2-methylbutanoyl]oxy-10-[(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: 4e7cdad7-3bfb-45f5-8fc5-f81058504e47
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aS,5S,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8-dihydroxy-8a-(hydroxymethyl)-5-methoxycarbonyl-5,6a,6b,11,11,14b-hexamethyl-9-[(2R)-2-methylbutanoyl]oxy-10-[(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): CCC(C)C(=O)OC1C(C(CC2C1(C(C(C3(C2=CCC4C3(CC(C5C4(CCC(C5)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)O)O)C)(C)C(=O)OC)C)C)O)O)CO)(C)C)OC(=O)C(=CC)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H]([C@@H]([C@@]3(C2=CC[C@H]4[C@]3(C[C@]([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(=O)OC)C)C)O)O)CO)(C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C52H80O20/c1-12-23(3)42(63)71-39-40(72-43(64)24(4)13-2)52(22-53)27(19-47(39,5)6)26-14-15-29-48(7)17-16-25(18-30(48)49(8,46(65)66-11)21-50(29,9)51(26,10)37(59)38(52)60)68-45-34(58)35(33(57)36(70-45)41(61)62)69-44-32(56)31(55)28(54)20-67-44/h12,14,24-25,27-40,44-45,53-60H,13,15-22H2,1-11H3,(H,61,62)/b23-12-/t24-,25+,27+,28+,29-,30+,31+,32-,33+,34-,35+,36+,37+,38-,39+,40+,44+,45-,48-,49+,50-,51+,52+/m1/s1
• InChI Key: RRFCVXKHZXHKIZ-OPJLIFMKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₀O₂₀
• Molecular Weight: 1025.20 g/mol
• Exact Mass: 1024.52429494 g/mol
• Topological Polar Surface Area (TPSA): 315.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8486	84.86%
Caco-2	-	0.8666	86.66%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8402	84.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8097	80.97%
OATP1B3 inhibitior	-	0.2667	26.67%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9392	93.92%
P-glycoprotein inhibitior	+	0.7490	74.90%
P-glycoprotein substrate	+	0.7283	72.83%
CYP3A4 substrate	+	0.7464	74.64%
CYP2C9 substrate	-	0.7978	79.78%
CYP2D6 substrate	-	0.8976	89.76%
CYP3A4 inhibition	-	0.6672	66.72%
CYP2C9 inhibition	-	0.8535	85.35%
CYP2C19 inhibition	-	0.8773	87.73%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	-	0.9080	90.80%
CYP2C8 inhibition	+	0.7587	75.87%
CYP inhibitory promiscuity	-	0.9618	96.18%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5811	58.11%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9003	90.03%
Skin irritation	-	0.6058	60.58%
Skin corrosion	-	0.9414	94.14%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7331	73.31%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6618	66.18%
skin sensitisation	-	0.8978	89.78%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8906	89.06%
Acute Oral Toxicity (c)	III	0.6959	69.59%
Estrogen receptor binding	+	0.7715	77.15%
Androgen receptor binding	+	0.7668	76.68%
Thyroid receptor binding	+	0.5771	57.71%
Glucocorticoid receptor binding	+	0.8122	81.22%
Aromatase binding	+	0.6453	64.53%
PPAR gamma	+	0.8295	82.95%
Honey bee toxicity	-	0.6837	68.37%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9475	94.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.86%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.52%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.30%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	95.97%	95.93%
CHEMBL2581	P07339	Cathepsin D	94.64%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.98%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.64%	96.77%
CHEMBL221	P23219	Cyclooxygenase-1	90.30%	90.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.28%	97.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.17%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.90%	86.33%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	88.12%	91.65%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.71%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.55%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.02%	94.33%
CHEMBL4208	P20618	Proteasome component C5	86.76%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.22%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.39%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.45%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.11%	96.90%
CHEMBL5957	P21589	5'-nucleotidase	83.88%	97.78%
CHEMBL340	P08684	Cytochrome P450 3A4	83.68%	91.19%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.12%	97.50%
CHEMBL5028	O14672	ADAM10	82.23%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.34%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.00%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.93%	95.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.59%	93.00%

Plants that contains it

• Polyspora chrysandra

Cross-Links

• PubChem: 163084726
• LOTUS: LTS0009922
• wikiData: Q105243986