(3R,4R,5S)-14'-[(2S,3R,4S,5R)-5-hydroxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7',9',13'-tetramethylspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene]-3,4,16'-triol

Details

• Internal ID: 6dd2f39d-64f9-4966-9c62-510225ba3378
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (3R,4R,5S)-14'-[(2S,3R,4S,5R)-5-hydroxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5,7',9',13'-tetramethylspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene]-3,4,16'-triol
• SMILES (Canonical): CC1COC2(CC3CC4C5CC=C6CC(CC(C6(C5CCC4(C3C2C)C)C)OC7C(C(C(CO7)O)OC8C(C(C(CO8)O)O)O)OC9C(C(C(C(O9)C)O)O)O)O)C(C1O)O
• SMILES (Isomeric): C[C@H]1COC2(CC3CC4C5CC=C6CC(CC(C6(C5CCC4(C3C2C)C)C)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O[C@H]9[C@@H]([C@@H]([C@@H]([C@@H](O9)C)O)O)O)O)[C@@H]([C@@H]1O)O
• InChI: InChI=1S/C44H70O17/c1-17-14-57-44(38(54)30(17)48)13-20-10-25-23-7-6-21-11-22(45)12-28(43(21,5)24(23)8-9-42(25,4)29(20)18(44)2)59-41-37(61-40-35(53)33(51)31(49)19(3)58-40)36(27(47)16-56-41)60-39-34(52)32(50)26(46)15-55-39/h6,17-20,22-41,45-54H,7-16H2,1-5H3/t17-,18?,19-,20?,22?,23?,24?,25?,26+,27+,28?,29?,30+,31+,32-,33+,34+,35+,36-,37+,38+,39-,40-,41-,42?,43?,44?/m0/s1
• InChI Key: NUNLNVBZEDMLNN-MQMSLHQRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₀O₁₇
• Molecular Weight: 871.00 g/mol
• Exact Mass: 870.46130076 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.93
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7875	78.75%
Caco-2	-	0.8850	88.50%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7195	71.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8672	86.72%
OATP1B3 inhibitior	+	0.9033	90.33%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7151	71.51%
P-glycoprotein inhibitior	+	0.7213	72.13%
P-glycoprotein substrate	+	0.7158	71.58%
CYP3A4 substrate	+	0.7570	75.70%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8212	82.12%
CYP3A4 inhibition	-	0.9732	97.32%
CYP2C9 inhibition	-	0.9268	92.68%
CYP2C19 inhibition	-	0.9293	92.93%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.9080	90.80%
CYP2C8 inhibition	+	0.7870	78.70%
CYP inhibitory promiscuity	-	0.9636	96.36%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5637	56.37%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9148	91.48%
Skin irritation	-	0.5366	53.66%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6464	64.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7266	72.66%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6320	63.20%
skin sensitisation	-	0.8995	89.95%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8859	88.59%
Acute Oral Toxicity (c)	I	0.4084	40.84%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.7387	73.87%
Thyroid receptor binding	-	0.5767	57.67%
Glucocorticoid receptor binding	-	0.5315	53.15%
Aromatase binding	+	0.6484	64.84%
PPAR gamma	+	0.7225	72.25%
Honey bee toxicity	-	0.6025	60.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9404	94.04%

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	98.43%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.90%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.73%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.14%	86.33%
CHEMBL1914	P06276	Butyrylcholinesterase	94.38%	95.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.37%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.35%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.84%	100.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	90.68%	85.31%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.58%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.97%	97.25%
CHEMBL2581	P07339	Cathepsin D	89.04%	98.95%
CHEMBL325	Q13547	Histone deacetylase 1	88.49%	95.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.28%	94.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	86.46%	97.53%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.10%	92.94%
CHEMBL5028	O14672	ADAM10	82.71%	97.50%
CHEMBL1871	P10275	Androgen Receptor	82.55%	96.43%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.25%	89.05%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.00%	93.04%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.84%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.50%	92.62%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.10%	97.21%

Plants that contains it

• Catha edulis

Cross-Links

• PubChem: 11968341
• NPASS: NPC192812