(2S,3R,8S,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,13,14-pentamethyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

Details

• Internal ID: 4195573d-4469-4b4d-8dab-c6b00ddb334f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2S,3R,8S,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-17-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,13,14-pentamethyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC1(C(C(CC2C1=CCC3C2(C(=O)CC4(C3(CC(C4C5(CCC(O5)C(C)(C)O)C)O)C)C)C)OC6C(C(C(C(O6)CO)O)O)O)O)C
• SMILES (Isomeric): C[C@@]1(CC[C@H](O1)C(C)(C)O)[C@H]2[C@@H](C[C@@]3([C@@]2(CC(=O)[C@@]4([C@H]3CC=C5[C@H]4C[C@@H]([C@@H](C5(C)C)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)C)O
• InChI: InChI=1S/C36H58O11/c1-31(2)17-9-10-22-33(5)14-19(38)28(35(7)12-11-24(47-35)32(3,4)44)34(33,6)15-23(39)36(22,8)18(17)13-20(29(31)43)45-30-27(42)26(41)25(40)21(16-37)46-30/h9,18-22,24-30,37-38,40-44H,10-16H2,1-8H3/t18-,19-,20+,21-,22+,24+,25-,26+,27-,28+,29+,30-,33+,34-,35-,36+/m1/s1
• InChI Key: STCKVNXTVGHORP-XXFNEMDQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₁₁
• Molecular Weight: 666.80 g/mol
• Exact Mass: 666.39791266 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9268	92.68%
Caco-2	-	0.8522	85.22%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8762	87.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8452	84.52%
OATP1B3 inhibitior	+	0.8560	85.60%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7703	77.03%
P-glycoprotein inhibitior	+	0.7264	72.64%
P-glycoprotein substrate	-	0.5977	59.77%
CYP3A4 substrate	+	0.7311	73.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.8141	81.41%
CYP2C9 inhibition	-	0.8376	83.76%
CYP2C19 inhibition	-	0.9269	92.69%
CYP2D6 inhibition	-	0.9303	93.03%
CYP1A2 inhibition	-	0.9115	91.15%
CYP2C8 inhibition	+	0.6044	60.44%
CYP inhibitory promiscuity	-	0.8822	88.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5232	52.32%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9248	92.48%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.8770	87.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7002	70.02%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5459	54.59%
skin sensitisation	-	0.9065	90.65%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7512	75.12%
Acute Oral Toxicity (c)	I	0.6410	64.10%
Estrogen receptor binding	+	0.6165	61.65%
Androgen receptor binding	+	0.7425	74.25%
Thyroid receptor binding	-	0.5477	54.77%
Glucocorticoid receptor binding	+	0.6853	68.53%
Aromatase binding	+	0.7184	71.84%
PPAR gamma	+	0.6492	64.92%
Honey bee toxicity	-	0.7048	70.48%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9722	97.22%

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	99.18%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.64%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.52%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.49%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.73%	96.21%
CHEMBL2581	P07339	Cathepsin D	92.15%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.72%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.07%	96.61%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.45%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.36%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.85%	93.04%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.63%	97.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.61%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.44%	86.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.43%	94.23%
CHEMBL259	P32245	Melanocortin receptor 4	87.19%	95.38%
CHEMBL1937	Q92769	Histone deacetylase 2	86.95%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.59%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.55%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	85.57%	95.93%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.93%	98.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.56%	96.95%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.53%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.19%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.44%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.40%	92.62%
CHEMBL2996	Q05655	Protein kinase C delta	80.34%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.23%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162928273
• LOTUS: LTS0060760
• wikiData: Q105260156