(2R,3R,4R,5S,6S)-2-[[(2R,3S,4S,5R,6S)-6-[(E)-2-[3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-7-hydroxy-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol

Details

• Internal ID: c4eedad0-41cf-46bc-9100-f7f1a478a72f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3R,4R,5S,6S)-2-[[(2R,3S,4S,5R,6S)-6-[(E)-2-[3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-7-hydroxy-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(C)(CCC=C(C)CO)C3CCC4(C3C(CC5C4(CCC6C5(CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)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)(CC/C=C(\C)/CO)C3CCC4(C3C(CC5C4(CCC6C5(CCC(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)CO)O)O)O)C)C)O)C)O)O)O)O)O)O
• InChI: InChI=1S/C54H92O23/c1-23(19-55)10-9-14-54(8,77-48-44(69)40(65)37(62)29(74-48)22-70-46-42(67)38(63)34(59)24(2)71-46)25-11-16-53(7)33(25)26(58)18-31-51(5)15-13-32(50(3,4)30(51)12-17-52(31,53)6)75-49-45(41(66)36(61)28(21-57)73-49)76-47-43(68)39(64)35(60)27(20-56)72-47/h10,24-49,55-69H,9,11-22H2,1-8H3/b23-10+/t24-,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-,51?,52?,53?,54?/m0/s1
• InChI Key: FYSLAFXFNUDGGL-DFYXEWSASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₂O₂₃
• Molecular Weight: 1109.30 g/mol
• Exact Mass: 1108.60293918 g/mol
• Topological Polar Surface Area (TPSA): 377.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -2.20
• H-Bond Acceptor: 23
• H-Bond Donor: 15
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9206	92.06%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8099	80.99%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8949	89.49%
P-glycoprotein inhibitior	+	0.7504	75.04%
P-glycoprotein substrate	-	0.5566	55.66%
CYP3A4 substrate	+	0.7396	73.96%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.7372	73.72%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9018	90.18%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.8124	81.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8536	85.36%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6110	61.10%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7809	78.09%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.8014	80.14%
Androgen receptor binding	+	0.7501	75.01%
Thyroid receptor binding	+	0.5586	55.86%
Glucocorticoid receptor binding	+	0.7454	74.54%
Aromatase binding	+	0.6517	65.17%
PPAR gamma	+	0.8018	80.18%
Honey bee toxicity	-	0.5501	55.01%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9172	91.72%

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	98.37%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	97.02%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.61%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.03%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.94%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.68%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	92.33%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.29%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.45%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.39%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.22%	92.94%
CHEMBL1951	P21397	Monoamine oxidase A	89.60%	91.49%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.27%	95.50%
CHEMBL2581	P07339	Cathepsin D	87.95%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.22%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.96%	93.04%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.13%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.60%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	83.31%	97.79%
CHEMBL259	P32245	Melanocortin receptor 4	83.06%	95.38%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.39%	95.83%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.94%	96.90%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.83%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.80%	94.75%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	81.65%	95.58%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.74%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.33%	97.14%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 11968559
• NPASS: NPC299191