(2R,3R,4S,5S,6R)-2-[[(3S,8S,9R,10R,11R,13R,14S,17R)-17-[(E,2R)-7-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-11-hydroxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: df1c9e5e-d3f4-4cca-9ca0-2f685c0a5c5c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(3S,8S,9R,10R,11R,13R,14S,17R)-17-[(E,2R)-7-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-11-hydroxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(CCC=C(C)COC1C(C(C(C(O1)CO)O)O)OC2C(C(C(C(O2)CO)O)O)O)C3CCC4(C3(CC(C5(C4CC=C6C5CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)O)C)O)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)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)[C@H]3CC[C@@]4([C@@]3(C[C@H]([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)O)C)C
• InChI: InChI=1S/C48H80O18/c1-22(21-61-44-41(38(58)35(55)29(20-51)64-44)66-43-40(60)37(57)34(54)28(19-50)63-43)9-8-10-23(2)24-15-16-46(5)30-13-11-25-26(48(30,7)31(52)17-47(24,46)6)12-14-32(45(25,3)4)65-42-39(59)36(56)33(53)27(18-49)62-42/h9,11,23-24,26-44,49-60H,8,10,12-21H2,1-7H3/b22-9+/t23-,24-,26-,27-,28-,29-,30+,31-,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42+,43+,44-,46+,47-,48+/m1/s1
• InChI Key: DPAJZQDHFKAPSC-DFKFRGTPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₀O₁₈
• Molecular Weight: 945.10 g/mol
• Exact Mass: 944.53446570 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): -0.25
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7547	75.47%
Caco-2	-	0.8893	88.93%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7664	76.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8377	83.77%
OATP1B3 inhibitior	-	0.2571	25.71%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8411	84.11%
P-glycoprotein inhibitior	+	0.7517	75.17%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7189	71.89%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9485	94.85%
CYP2C9 inhibition	-	0.8767	87.67%
CYP2C19 inhibition	-	0.9161	91.61%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.9112	91.12%
CYP2C8 inhibition	+	0.6841	68.41%
CYP inhibitory promiscuity	-	0.9421	94.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9056	90.56%
Skin irritation	-	0.5835	58.35%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.7637	76.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8489	84.89%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7676	76.76%
skin sensitisation	-	0.8992	89.92%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7708	77.08%
Acute Oral Toxicity (c)	III	0.5598	55.98%
Estrogen receptor binding	+	0.8237	82.37%
Androgen receptor binding	+	0.7612	76.12%
Thyroid receptor binding	+	0.5229	52.29%
Glucocorticoid receptor binding	+	0.7066	70.66%
Aromatase binding	+	0.6529	65.29%
PPAR gamma	+	0.7990	79.90%
Honey bee toxicity	-	0.6705	67.05%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9262	92.62%

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	97.80%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.53%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.34%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.74%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.57%	96.61%
CHEMBL2581	P07339	Cathepsin D	91.45%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.33%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.78%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.67%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.80%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.74%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.55%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.67%	96.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.69%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.12%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.46%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	82.37%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.19%	97.25%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.15%	97.47%
CHEMBL1873	P00750	Tissue-type plasminogen activator	80.22%	93.33%

Plants that contains it

• Hemsleya carnosiflora
• Hemsleya panacis-scandens

Cross-Links

• PubChem: 101662048
• LOTUS: LTS0132952
• wikiData: Q104393810