(8S,9R,10R,13R,14S,16R,17R)-17-[(2R,5R)-2,6-dihydroxy-6-methyl-3-oxo-5-(7H-purin-6-ylamino)heptan-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione

Details

• Internal ID: e72dd3bc-31b2-404f-bab5-78b7030c2756
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (8S,9R,10R,13R,14S,16R,17R)-17-[(2R,5R)-2,6-dihydroxy-6-methyl-3-oxo-5-(7H-purin-6-ylamino)heptan-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
• SMILES (Canonical): CC1(C2=CCC3C4(CC(C(C4(CC(=O)C3(C2C=C(C1=O)OC5C(C(C(C(O5)CO)O)O)O)C)C)C(C)(C(=O)CC(C(C)(C)O)NC6=NC=NC7=C6NC=N7)O)O)C)C
• SMILES (Isomeric): C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)C)C)[C@](C)(C(=O)C[C@H](C(C)(C)O)NC6=NC=NC7=C6NC=N7)O)O
• InChI: InChI=1S/C41H57N5O12/c1-36(2)18-9-10-23-38(5)13-20(48)31(41(8,56)25(49)12-24(37(3,4)55)46-34-27-33(43-16-42-27)44-17-45-34)39(38,6)14-26(50)40(23,7)19(18)11-21(32(36)54)57-35-30(53)29(52)28(51)22(15-47)58-35/h9,11,16-17,19-20,22-24,28-31,35,47-48,51-53,55-56H,10,12-15H2,1-8H3,(H2,42,43,44,45,46)/t19-,20-,22-,23+,24-,28+,29+,30-,31+,35-,38+,39-,40+,41+/m1/s1
• InChI Key: MREUELDSJSOJLT-UXSHJATCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₅₇N₅O₁₂
• Molecular Weight: 811.90 g/mol
• Exact Mass: 811.40037227 g/mol
• Topological Polar Surface Area (TPSA): 278.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9201	92.01%
Caco-2	-	0.8583	85.83%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.3421	34.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8364	83.64%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7472	74.72%
P-glycoprotein inhibitior	+	0.7465	74.65%
P-glycoprotein substrate	+	0.6585	65.85%
CYP3A4 substrate	+	0.7376	73.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8689	86.89%
CYP3A4 inhibition	-	0.9079	90.79%
CYP2C9 inhibition	-	0.8280	82.80%
CYP2C19 inhibition	-	0.8253	82.53%
CYP2D6 inhibition	-	0.9010	90.10%
CYP1A2 inhibition	-	0.7916	79.16%
CYP2C8 inhibition	+	0.7694	76.94%
CYP inhibitory promiscuity	-	0.7565	75.65%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4897	48.97%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.9049	90.49%
Skin irritation	-	0.7447	74.47%
Skin corrosion	-	0.9233	92.33%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6886	68.86%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.5765	57.65%
skin sensitisation	-	0.8342	83.42%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.4910	49.10%
Acute Oral Toxicity (c)	III	0.6236	62.36%
Estrogen receptor binding	+	0.7351	73.51%
Androgen receptor binding	+	0.7652	76.52%
Thyroid receptor binding	+	0.6179	61.79%
Glucocorticoid receptor binding	+	0.7790	77.90%
Aromatase binding	+	0.6431	64.31%
PPAR gamma	+	0.7774	77.74%
Honey bee toxicity	-	0.6362	63.62%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9762	97.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.10%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.66%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.04%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.93%	97.09%
CHEMBL2581	P07339	Cathepsin D	95.59%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.07%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.66%	89.34%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.71%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.17%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	92.93%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.50%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.74%	96.77%
CHEMBL4208	P20618	Proteasome component C5	84.12%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.18%	100.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.80%	97.53%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.34%	89.00%
CHEMBL290	Q13370	Phosphodiesterase 3B	82.01%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.78%	94.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.77%	91.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.65%	95.89%
CHEMBL2535	P11166	Glucose transporter	81.43%	98.75%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.75%	96.61%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.41%	96.90%

Plants that contains it

• Cucurbita pepo

Cross-Links

• PubChem: 162996245
• LOTUS: LTS0086462
• wikiData: Q105170523