3-[[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,8R,10R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid

Details

• Internal ID: 8a1230af-475b-4d77-b36a-09d5327d3b96
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: 3-[[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,8R,10R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(C)(CCC=C(C)C)C3CCC4(C3C(CC5C4(CCC6C5(CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)COC(=O)CC(=O)O)O)O)O)C)C)O)C)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(C)(CCC=C(C)C)C3CCC4(C3C(CC5[C@]4(CCC6[C@@]5(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)COC(=O)CC(=O)O)O)O)O)C)C)O)C)O)O)O)O)O)O
• InChI: InChI=1S/C57H94O25/c1-24(2)11-10-15-57(9,82-51-47(73)43(69)40(66)30(79-51)23-75-49-45(71)41(67)37(63)25(3)76-49)26-12-17-56(8)36(26)27(59)19-32-54(6)16-14-33(53(4,5)31(54)13-18-55(32,56)7)80-52-48(44(70)38(64)28(21-58)77-52)81-50-46(72)42(68)39(65)29(78-50)22-74-35(62)20-34(60)61/h11,25-33,36-52,58-59,63-73H,10,12-23H2,1-9H3,(H,60,61)/t25-,26?,27?,28+,29+,30+,31?,32?,33-,36?,37+,38+,39+,40+,41+,42-,43-,44-,45+,46+,47+,48+,49+,50-,51-,52-,54-,55+,56?,57?/m0/s1
• InChI Key: DBGMBTZQBJWAQO-DYDRFSEASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₉₄O₂₅
• Molecular Weight: 1179.30 g/mol
• Exact Mass: 1178.60841848 g/mol
• Topological Polar Surface Area (TPSA): 400.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -1.15
• H-Bond Acceptor: 24
• H-Bond Donor: 14
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7431	74.31%
Caco-2	-	0.8819	88.19%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8360	83.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7879	78.79%
OATP1B3 inhibitior	+	0.8203	82.03%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.9515	95.15%
P-glycoprotein inhibitior	+	0.7458	74.58%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7416	74.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.8860	88.60%
CYP2C9 inhibition	-	0.8463	84.63%
CYP2C19 inhibition	-	0.9234	92.34%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.9169	91.69%
CYP2C8 inhibition	+	0.7543	75.43%
CYP inhibitory promiscuity	-	0.9609	96.09%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6365	63.65%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8989	89.89%
Skin irritation	-	0.5364	53.64%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.7424	74.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7772	77.72%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5892	58.92%
skin sensitisation	-	0.9102	91.02%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7738	77.38%
Acute Oral Toxicity (c)	III	0.5258	52.58%
Estrogen receptor binding	+	0.7744	77.44%
Androgen receptor binding	+	0.7435	74.35%
Thyroid receptor binding	+	0.5950	59.50%
Glucocorticoid receptor binding	+	0.7852	78.52%
Aromatase binding	+	0.6635	66.35%
PPAR gamma	+	0.8251	82.51%
Honey bee toxicity	-	0.5806	58.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9586	95.86%

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	98.23%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.28%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.85%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.24%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.95%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.88%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.89%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.27%	97.09%
CHEMBL5028	O14672	ADAM10	89.09%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	88.45%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.07%	89.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.84%	96.90%
CHEMBL2581	P07339	Cathepsin D	87.75%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.68%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	86.93%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.83%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.91%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.67%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	84.12%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	83.94%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.75%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.65%	91.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.56%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.96%	93.04%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.45%	89.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.37%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.03%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.67%	93.00%
CHEMBL1914	P06276	Butyrylcholinesterase	80.49%	95.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.12%	97.50%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 24893634
• NPASS: NPC206537