(1S,2S,4R,6S,7S,8R,9S,10R,13S,14S)-7,8-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-enyl)-16-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-15,19-diene-12,17-dione

Details

• Internal ID: fe53f9a3-0f97-4189-bfc4-13ee786e9d5f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (1S,2S,4R,6S,7S,8R,9S,10R,13S,14S)-7,8-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-enyl)-16-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-15,19-diene-12,17-dione
• SMILES (Canonical): CC(=CC1C(C(C2C(O1)CC3(C2(CC(=O)C4(C3CC=C5C4C=C(C(=O)C5(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)C)C)(C)O)O)C
• SMILES (Isomeric): CC(=C[C@H]1[C@@H]([C@]([C@@H]2[C@H](O1)C[C@@]3([C@@]2(CC(=O)[C@]4([C@H]3CC=C5[C@@H]4C=C(C(=O)C5(C)C)O[C@@H]6[C@@H]([C@@H]([C@H]([C@H](O6)CO)O)O)O)C)C)C)(C)O)O)C
• InChI: InChI=1S/C36H52O11/c1-16(2)11-19-30(43)36(8,44)28-21(45-19)13-33(5)23-10-9-17-18(35(23,7)24(38)14-34(28,33)6)12-20(29(42)32(17,3)4)46-31-27(41)26(40)25(39)22(15-37)47-31/h9,11-12,18-19,21-23,25-28,30-31,37,39-41,43-44H,10,13-15H2,1-8H3/t18-,19-,21+,22+,23-,25-,26+,27+,28+,30-,31-,33-,34+,35+,36+/m0/s1
• InChI Key: YROWDXFQJCHNIN-WTQJVNLOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₂O₁₁
• Molecular Weight: 660.80 g/mol
• Exact Mass: 660.35096247 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.72
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8609	86.09%
Caco-2	-	0.8554	85.54%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8547	85.47%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8590	85.90%
OATP1B3 inhibitior	+	0.7886	78.86%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7039	70.39%
P-glycoprotein inhibitior	+	0.7250	72.50%
P-glycoprotein substrate	-	0.5732	57.32%
CYP3A4 substrate	+	0.6938	69.38%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8874	88.74%
CYP3A4 inhibition	-	0.8528	85.28%
CYP2C9 inhibition	-	0.8605	86.05%
CYP2C19 inhibition	-	0.9282	92.82%
CYP2D6 inhibition	-	0.9511	95.11%
CYP1A2 inhibition	-	0.8952	89.52%
CYP2C8 inhibition	+	0.5491	54.91%
CYP inhibitory promiscuity	-	0.8987	89.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6196	61.96%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9159	91.59%
Skin irritation	-	0.5849	58.49%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.6278	62.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6850	68.50%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6927	69.27%
skin sensitisation	-	0.8947	89.47%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6619	66.19%
Acute Oral Toxicity (c)	III	0.6039	60.39%
Estrogen receptor binding	+	0.7676	76.76%
Androgen receptor binding	+	0.7383	73.83%
Thyroid receptor binding	+	0.5463	54.63%
Glucocorticoid receptor binding	+	0.7685	76.85%
Aromatase binding	+	0.7169	71.69%
PPAR gamma	+	0.7082	70.82%
Honey bee toxicity	-	0.6594	65.94%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9860	98.60%

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	99.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.03%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.84%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.60%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.74%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.73%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.76%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.38%	96.77%
CHEMBL4072	P07858	Cathepsin B	85.29%	93.67%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.34%	96.61%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.76%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	81.55%	94.73%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	81.03%	87.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.80%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.72%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.71%	95.83%

Plants that contains it

• Trichosanthes tricuspidata

Cross-Links

• PubChem: 163025185
• LOTUS: LTS0118437
• wikiData: Q105352942