(23S)-17,23-Epoxy-29-hydroxy-3beta-[6-O-[2-O-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-alpha-L-arabinopyranosyl]-beta-D-glucopyranosyloxy]-27-norlanosta-8-ene-15,24-dione

Details

• Internal ID: b37b72e7-e5eb-429c-9a89-29643081ff3d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,3'R,4S,5R,5'S,10S,13S,14S,17S)-3-[(2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-(hydroxymethyl)-3',4,10,13,14-pentamethyl-5'-propanoylspiro[2,3,5,6,7,11,12,16-octahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-15-one
• SMILES (Canonical): CCC(=O)C1CC(C2(O1)CC(=O)C3(C2(CCC4=C3CCC5C4(CCC(C5(C)CO)OC6C(C(C(C(O6)COC7C(C(C(CO7)O)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)C)O)O)O)O)O)O)C)C)C)C
• SMILES (Isomeric): CCC(=O)[C@@H]1C[C@H]([C@@]2(O1)CC(=O)[C@@]3([C@@]2(CCC4=C3CC[C@@H]5[C@@]4(CC[C@@H]([C@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)O)O)O)C)C)C)C
• InChI: InChI=1S/C52H82O23/c1-8-25(55)27-15-21(2)52(75-27)16-31(57)51(7)24-9-10-30-48(4,23(24)11-14-50(51,52)6)13-12-32(49(30,5)20-54)72-45-41(66)38(63)36(61)29(71-45)19-68-46-42(34(59)26(56)18-67-46)74-47-43(39(64)35(60)28(17-53)70-47)73-44-40(65)37(62)33(58)22(3)69-44/h21-22,26-30,32-47,53-54,56,58-66H,8-20H2,1-7H3/t21-,22+,26+,27+,28-,29-,30-,32+,33+,34+,35-,36-,37-,38+,39+,40-,41-,42-,43-,44+,45+,46+,47+,48-,49-,50+,51-,52+/m1/s1
• InChI Key: POPCDORNWGKDIG-VMFKSRKESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₂O₂₃
• Molecular Weight: 1075.20 g/mol
• Exact Mass: 1074.52468886 g/mol
• Topological Polar Surface Area (TPSA): 360.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -2.26
• H-Bond Acceptor: 23
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8843	88.43%
Caco-2	-	0.8758	87.58%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8293	82.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8178	81.78%
OATP1B3 inhibitior	+	0.9075	90.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9358	93.58%
P-glycoprotein inhibitior	+	0.7477	74.77%
P-glycoprotein substrate	+	0.6908	69.08%
CYP3A4 substrate	+	0.7414	74.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8581	85.81%
CYP3A4 inhibition	-	0.6466	64.66%
CYP2C9 inhibition	-	0.8830	88.30%
CYP2C19 inhibition	-	0.9109	91.09%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	-	0.9156	91.56%
CYP2C8 inhibition	+	0.7590	75.90%
CYP inhibitory promiscuity	-	0.9286	92.86%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4586	45.86%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9027	90.27%
Skin irritation	+	0.6083	60.83%
Skin corrosion	-	0.9367	93.67%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8157	81.57%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7101	71.01%
skin sensitisation	-	0.9298	92.98%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6665	66.65%
Acute Oral Toxicity (c)	III	0.5966	59.66%
Estrogen receptor binding	+	0.8159	81.59%
Androgen receptor binding	+	0.7534	75.34%
Thyroid receptor binding	+	0.5451	54.51%
Glucocorticoid receptor binding	+	0.7337	73.37%
Aromatase binding	+	0.6307	63.07%
PPAR gamma	+	0.8069	80.69%
Honey bee toxicity	-	0.6483	64.83%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9720	97.20%

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	98.47%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.84%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.90%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.84%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.42%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.94%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.51%	98.95%
CHEMBL259	P32245	Melanocortin receptor 4	89.87%	95.38%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.28%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.87%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.32%	94.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.25%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.16%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.68%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.11%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.98%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	85.71%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.68%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.46%	91.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	85.41%	96.90%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.96%	97.36%
CHEMBL340	P08684	Cytochrome P450 3A4	84.88%	91.19%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.30%	98.00%
CHEMBL1902	P62942	FK506-binding protein 1A	83.22%	97.05%
CHEMBL1951	P21397	Monoamine oxidase A	83.10%	91.49%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.14%	95.83%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.80%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.27%	95.56%
CHEMBL1871	P10275	Androgen Receptor	80.23%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	80.13%	92.50%

Plants that contains it

• Bellevalia paradoxa
• Leopoldia comosa

Cross-Links

• PubChem: 44559606
• LOTUS: LTS0021673
• wikiData: Q105212586