(3R,4R,5S,6S)-2-methyl-6-[4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptane-2,3,4,5-tetrol

Details

• Internal ID: 22273c5c-2477-412c-8bab-6111a12eaba8
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (3R,4R,5S,6S)-2-methyl-6-[4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptane-2,3,4,5-tetrol
• SMILES (Canonical): CC(C1CCC2(C1(CCC3(C2CC=C4C3CCC(C4(C)C)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)C)C)C)C(C(C(C(C)(C)O)O)O)O
• SMILES (Isomeric): C[C@@H](C1CCC2(C1(CCC3(C2CC=C4C3CCC(C4(C)C)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O)O)O)O)O)O)C)C)C)[C@@H]([C@H]([C@H](C(C)(C)O)O)O)O
• InChI: InChI=1S/C42H72O15/c1-19(27(44)32(49)35(52)39(4,5)53)20-13-14-42(8)25-11-9-21-22(40(25,6)15-16-41(20,42)7)10-12-26(38(21,2)3)57-37-34(51)31(48)29(46)24(56-37)18-54-36-33(50)30(47)28(45)23(17-43)55-36/h9,19-20,22-37,43-53H,10-18H2,1-8H3/t19-,20?,22?,23+,24+,25?,26?,27-,28-,29-,30-,31-,32+,33+,34+,35+,36+,37-,40?,41?,42?/m0/s1
• InChI Key: WBYJYPOPDKQBQJ-DKZHGXJWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₂O₁₅
• Molecular Weight: 817.00 g/mol
• Exact Mass: 816.48712159 g/mol
• Topological Polar Surface Area (TPSA): 259.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.09
• H-Bond Acceptor: 15
• H-Bond Donor: 11
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7122	71.22%
Caco-2	-	0.8833	88.33%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8033	80.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8405	84.05%
OATP1B3 inhibitior	-	0.3092	30.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.5084	50.84%
P-glycoprotein inhibitior	+	0.7409	74.09%
P-glycoprotein substrate	-	0.5357	53.57%
CYP3A4 substrate	+	0.7028	70.28%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.9631	96.31%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.9059	90.59%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.8883	88.83%
CYP2C8 inhibition	+	0.6785	67.85%
CYP inhibitory promiscuity	-	0.9012	90.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6129	61.29%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9109	91.09%
Skin irritation	-	0.6298	62.98%
Skin corrosion	-	0.9462	94.62%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7607	76.07%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7334	73.34%
skin sensitisation	-	0.9020	90.20%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.7948	79.48%
Acute Oral Toxicity (c)	III	0.6471	64.71%
Estrogen receptor binding	+	0.7942	79.42%
Androgen receptor binding	+	0.7169	71.69%
Thyroid receptor binding	-	0.5625	56.25%
Glucocorticoid receptor binding	+	0.6161	61.61%
Aromatase binding	+	0.6339	63.39%
PPAR gamma	+	0.7418	74.18%
Honey bee toxicity	-	0.7274	72.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9499	94.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.61%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.82%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.09%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.40%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.90%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	89.96%	97.79%
CHEMBL226	P30542	Adenosine A1 receptor	89.95%	95.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.40%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.15%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.96%	96.21%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	85.82%	100.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.02%	98.05%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.93%	93.56%
CHEMBL1977	P11473	Vitamin D receptor	83.95%	99.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.83%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	83.68%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.66%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.77%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.80%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.62%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.21%	92.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.71%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.70%	95.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.68%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.62%	89.00%
CHEMBL5028	O14672	ADAM10	80.58%	97.50%

Plants that contains it

• Annona reticulata
• Annona squamosa

Cross-Links

• PubChem: 6325702
• NPASS: NPC219753