(3S,8S,9R,10R,13R,14S,17R)-17-[(E,2R)-7-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-4,4,9,13,14-pentamethyl-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: 2579992e-2de1-428b-acd4-5634bc282ebe
• 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)-17-[(E,2R)-7-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-4,4,9,13,14-pentamethyl-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)CO)O)O)OC2C(C(C(C(O2)CO)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)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(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(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/h9,11,23-24,26-30,32-44,49-51,53-60H,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: DRSIUFQRQCNVHS-IJJXDQGGSA-N
• Popularity: 3 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: 1.50
• 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	-	0.8827	88.27%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8651	86.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8265	82.65%
OATP1B3 inhibitior	-	0.4111	41.11%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8627	86.27%
P-glycoprotein inhibitior	+	0.7523	75.23%
P-glycoprotein substrate	-	0.5338	53.38%
CYP3A4 substrate	+	0.7230	72.30%
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	+	0.6228	62.28%
CYP inhibitory promiscuity	-	0.9193	91.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6168	61.68%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9054	90.54%
Skin irritation	-	0.5922	59.22%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8080	80.80%
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	-	0.6888	68.88%
Acute Oral Toxicity (c)	III	0.7126	71.26%
Estrogen receptor binding	+	0.8160	81.60%
Androgen receptor binding	+	0.7633	76.33%
Thyroid receptor binding	+	0.5323	53.23%
Glucocorticoid receptor binding	+	0.7555	75.55%
Aromatase binding	+	0.6324	63.24%
PPAR gamma	+	0.7993	79.93%
Honey bee toxicity	-	0.6891	68.91%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	98.31%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.58%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.41%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.67%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	91.75%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.75%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.21%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.14%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.08%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.48%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.42%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.46%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.84%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.36%	93.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.85%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	81.63%	94.73%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.34%	93.04%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.07%	90.08%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.84%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	80.24%	93.18%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.10%	99.23%

Plants that contains it

• Hemsleya carnosiflora
• Hemsleya panacis-scandens

Cross-Links

• PubChem: 101662047
• LOTUS: LTS0010629
• wikiData: Q104393808