(2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-[3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-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]-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol

Details

• Internal ID: 19cb7421-927e-418e-aa6d-09feaed32c12
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-[3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-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]-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)C)C3CCC4(C3C(CC5C4(CCC6C5(CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(CO8)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(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](CO8)O)O)O)C)C)O)C)O)O)O)O)O)O
• InChI: InChI=1S/C53H90O21/c1-23(2)11-10-15-53(9,74-47-43(66)39(62)37(60)29(71-47)22-68-45-42(65)38(61)34(57)24(3)69-45)25-12-17-52(8)33(25)26(55)19-31-50(6)16-14-32(49(4,5)30(50)13-18-51(31,52)7)72-48-44(40(63)36(59)28(20-54)70-48)73-46-41(64)35(58)27(56)21-67-46/h11,24-48,54-66H,10,12-22H2,1-9H3/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-,50?,51?,52?,53?/m0/s1
• InChI Key: XTDZKFZZAQRWGE-YCQLJQLHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₉₀O₂₁
• Molecular Weight: 1063.30 g/mol
• Exact Mass: 1062.59745988 g/mol
• Topological Polar Surface Area (TPSA): 337.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 14

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	-	0.9160	91.60%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7952	79.52%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9026	90.26%
P-glycoprotein inhibitior	+	0.7533	75.33%
P-glycoprotein substrate	-	0.5434	54.34%
CYP3A4 substrate	+	0.7375	73.75%
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	+	0.7415	74.15%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9021	90.21%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8300	83.00%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5694	56.94%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8729	87.29%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.8006	80.06%
Androgen receptor binding	+	0.7322	73.22%
Thyroid receptor binding	+	0.5539	55.39%
Glucocorticoid receptor binding	+	0.7602	76.02%
Aromatase binding	+	0.6571	65.71%
PPAR gamma	+	0.8065	80.65%
Honey bee toxicity	-	0.5539	55.39%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	98.72%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.38%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	96.63%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.20%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.07%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.06%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.54%	92.94%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.41%	96.61%
CHEMBL1951	P21397	Monoamine oxidase A	90.88%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.53%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.29%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.09%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	89.91%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.14%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.59%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.15%	98.95%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	85.70%	100.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.42%	95.58%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.87%	95.83%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.55%	82.69%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.48%	96.90%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.98%	100.00%
CHEMBL5028	O14672	ADAM10	82.84%	97.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.82%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.00%	91.24%
CHEMBL2094128	P24941	Cyclin-dependent kinase 2/cyclin A	80.98%	97.25%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.62%	92.88%
CHEMBL1977	P11473	Vitamin D receptor	80.37%	99.43%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 6325313
• NPASS: NPC10054
• LOTUS: LTS0184429
• wikiData: Q105341506