(3S,8S,9R,10R,13R,14S,17R)-4,4,9,13,14-pentamethyl-17-[(Z,2R)-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-3-[(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: c7a3cc2f-a4da-4062-bf46-3a754e708bc0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (3S,8S,9R,10R,13R,14S,17R)-4,4,9,13,14-pentamethyl-17-[(Z,2R)-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-3-[(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): CC(CCC=C(C)COC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O)C3CCC4(C3(CC(=O)C5(C4CC=C6C5CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)O)C)C)C
• SMILES (Isomeric): C[C@H](CC/C=C(/C)\CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)[C@H]3CC[C@@]4([C@@]3(CC(=O)[C@@]5([C@H]4CC=C6[C@H]5CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)C
• InChI: InChI=1S/C48H78O18/c1-22(20-61-42-40(59)38(57)35(54)29(65-42)21-62-43-39(58)36(55)33(52)27(18-49)63-43)9-8-10-23(2)24-15-16-46(5)30-13-11-25-26(48(30,7)31(51)17-47(24,46)6)12-14-32(45(25,3)4)66-44-41(60)37(56)34(53)28(19-50)64-44/h9,11,23-24,26-30,32-44,49-50,52-60H,8,10,12-21H2,1-7H3/b22-9-/t23-,24-,26-,27-,28-,29-,30+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42-,43-,44+,46+,47-,48+/m1/s1
• InChI Key: UHWXBWBOPABGIG-OUPFKYCMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₈O₁₈
• Molecular Weight: 943.10 g/mol
• Exact Mass: 942.51881563 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): -0.04
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7907	79.07%
Caco-2	-	0.8809	88.09%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8651	86.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8197	81.97%
OATP1B3 inhibitior	-	0.4111	41.11%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8447	84.47%
P-glycoprotein inhibitior	+	0.7513	75.13%
P-glycoprotein substrate	-	0.5172	51.72%
CYP3A4 substrate	+	0.7202	72.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8581	85.81%
CYP3A4 inhibition	-	0.9642	96.42%
CYP2C9 inhibition	-	0.8723	87.23%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.8907	89.07%
CYP2C8 inhibition	+	0.6127	61.27%
CYP inhibitory promiscuity	-	0.9193	91.93%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6168	61.68%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9051	90.51%
Skin irritation	-	0.5922	59.22%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7855	78.55%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6754	67.54%
skin sensitisation	-	0.9044	90.44%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.6560	65.60%
Acute Oral Toxicity (c)	III	0.7126	71.26%
Estrogen receptor binding	+	0.8041	80.41%
Androgen receptor binding	+	0.7568	75.68%
Thyroid receptor binding	+	0.5463	54.63%
Glucocorticoid receptor binding	+	0.7640	76.40%
Aromatase binding	+	0.6649	66.49%
PPAR gamma	+	0.7969	79.69%
Honey bee toxicity	-	0.7050	70.50%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9649	96.49%

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	98.42%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.74%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.44%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.39%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	93.85%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.21%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.13%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.07%	86.33%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.59%	93.04%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.80%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.48%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.11%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.97%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.53%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.13%	93.00%
CHEMBL4581	P52732	Kinesin-like protein 1	83.00%	93.18%
CHEMBL5255	O00206	Toll-like receptor 4	82.37%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.91%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.91%	99.23%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.32%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.74%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	80.71%	94.73%

Plants that contains it

• Butea monosperma
• Hemsleya panacis-scandens

Cross-Links

• PubChem: 163192216
• LOTUS: LTS0252335
• wikiData: Q105236664