MogrosideIV

Details

• Internal ID: 71ccf0ae-5cb1-434c-977f-9ea300b36136
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(3S,8S,9R,10R,11R,13R,14S,17R)-17-[(2R,5R)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-hydroxy-6-methylheptan-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]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(CCC(C(C)(C)O)OC1C(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)COC8C(C(C(C(O8)CO)O)O)O)O)O)O)C)O)C)C
• SMILES (Isomeric): C[C@H](CC[C@H](C(C)(C)O)O[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[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)C)O)C)C
• InChI: InChI=1S/C54H92O24/c1-22(9-13-33(51(4,5)70)77-49-45(41(66)36(61)28(20-57)74-49)78-48-44(69)39(64)35(60)27(19-56)73-48)23-15-16-52(6)30-12-10-24-25(54(30,8)31(58)17-53(23,52)7)11-14-32(50(24,2)3)76-47-43(68)40(65)37(62)29(75-47)21-71-46-42(67)38(63)34(59)26(18-55)72-46/h10,22-23,25-49,55-70H,9,11-21H2,1-8H3/t22-,23-,25-,26-,27+,28-,29-,30+,31-,32+,33-,34-,35+,36-,37-,38+,39-,40+,41+,42-,43-,44+,45-,46-,47+,48-,49+,52+,53-,54+/m1/s1
• InChI Key: WRPAFPPCKSYACJ-YCEJTGPGSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₂O₂₄
• Molecular Weight: 1125.30 g/mol
• Exact Mass: 1124.59785380 g/mol
• Topological Polar Surface Area (TPSA): 398.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -3.23
• H-Bond Acceptor: 24
• H-Bond Donor: 16
• Rotatable Bonds: 17

Synonyms

• MogrosideIV
• 89590-95-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7547	75.47%
Caco-2	-	0.8914	89.14%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7664	76.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8580	85.80%
OATP1B3 inhibitior	-	0.2571	25.71%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7538	75.38%
P-glycoprotein inhibitior	+	0.7480	74.80%
P-glycoprotein substrate	+	0.5643	56.43%
CYP3A4 substrate	+	0.7266	72.66%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
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	+	0.6721	67.21%
CYP inhibitory promiscuity	-	0.9421	94.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9012	90.12%
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	+	0.8041	80.41%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6979	69.79%
skin sensitisation	-	0.8992	89.92%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6613	66.13%
Acute Oral Toxicity (c)	III	0.5598	55.98%
Estrogen receptor binding	+	0.8012	80.12%
Androgen receptor binding	+	0.7542	75.42%
Thyroid receptor binding	+	0.5386	53.86%
Glucocorticoid receptor binding	+	0.7212	72.12%
Aromatase binding	+	0.6496	64.96%
PPAR gamma	+	0.7929	79.29%
Honey bee toxicity	-	0.6702	67.02%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.78%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.30%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.11%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.11%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.62%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.45%	93.04%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.37%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.25%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.16%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.80%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.13%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.27%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.21%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	85.87%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.03%	89.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.72%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.65%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.51%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.38%	95.56%
CHEMBL5028	O14672	ADAM10	84.32%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.07%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	83.87%	97.79%
CHEMBL2094135	Q96BI3	Gamma-secretase	83.49%	98.05%
CHEMBL1871	P10275	Androgen Receptor	82.55%	96.43%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.54%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.73%	96.90%
CHEMBL1977	P11473	Vitamin D receptor	81.33%	99.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.93%	94.00%
CHEMBL1907	P15144	Aminopeptidase N	80.62%	93.31%
CHEMBL1873	P00750	Tissue-type plasminogen activator	80.53%	93.33%

Plants that contains it

• Siraitia grosvenorii
• Siraitia siamensis

Cross-Links

• PubChem: 145710145
• LOTUS: LTS0138650
• wikiData: Q105311487