(3R,3'R,4R,5R,5'S,10R,13S,14R,17S)-3-[(2S,3R,4R,5R,6R)-6-[[(2S,3S,4S,5R)-3-[(2S,3R,4R,5S,6R)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-(hydroxymethyl)-3',4,5',10,13,14-hexamethyl-5'-propanoylspiro[2,3,5,6,7,11,12,16-octahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-15-one

Details

• Internal ID: a88aa3c7-7033-4aa1-8825-9cd54d190567
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,3'R,4R,5R,5'S,10R,13S,14R,17S)-3-[(2S,3R,4R,5R,6R)-6-[[(2S,3S,4S,5R)-3-[(2S,3R,4R,5S,6R)-3-[(2S,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-(hydroxymethyl)-3',4,5',10,13,14-hexamethyl-5'-propanoylspiro[2,3,5,6,7,11,12,16-octahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-15-one
• SMILES (Canonical): CCC(=O)C1(CC(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(CO9)(CO)O)O)O)O)O)C)C)C)C)C
• SMILES (Isomeric): CCC(=O)[C@@]1(C[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@@](CO9)(CO)O)O)O)O)O)C)C)C)C)C
• InChI: InChI=1S/C52H82O23/c1-8-30(57)48(5)15-23(2)52(75-48)16-31(58)50(7)25-9-10-29-46(3,24(25)11-14-49(50,52)6)13-12-32(47(29,4)20-54)72-42-38(64)36(62)35(61)28(71-42)19-68-43-39(33(59)26(56)18-67-43)73-44-40(37(63)34(60)27(17-53)70-44)74-45-41(65)51(66,21-55)22-69-45/h23,26-29,32-45,53-56,59-66H,8-22H2,1-7H3/t23-,26-,27-,28-,29-,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: VYJUXLFTQPZHRI-GCJXZTHESA-N
• Popularity: 0 references 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: 14

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	-	0.8715	87.15%
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	+	0.8192	81.92%
OATP1B3 inhibitior	+	0.9075	90.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9305	93.05%
P-glycoprotein inhibitior	+	0.7469	74.69%
P-glycoprotein substrate	+	0.7129	71.29%
CYP3A4 substrate	+	0.7474	74.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8671	86.71%
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	+	0.7832	78.32%
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	-	0.9010	90.10%
Skin irritation	+	0.6083	60.83%
Skin corrosion	-	0.9367	93.67%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8298	82.98%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6851	68.51%
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	+	0.6544	65.44%
Acute Oral Toxicity (c)	III	0.5966	59.66%
Estrogen receptor binding	+	0.7785	77.85%
Androgen receptor binding	+	0.7611	76.11%
Thyroid receptor binding	+	0.5553	55.53%
Glucocorticoid receptor binding	+	0.7143	71.43%
Aromatase binding	+	0.6210	62.10%
PPAR gamma	+	0.7854	78.54%
Honey bee toxicity	-	0.6537	65.37%
Biodegradation	-	0.7000	70.00%
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	97.99%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.94%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.25%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.93%	92.94%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.55%	91.24%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.16%	86.92%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.88%	99.23%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.90%	83.57%
CHEMBL221	P23219	Cyclooxygenase-1	90.72%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.38%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.86%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.65%	95.93%
CHEMBL2581	P07339	Cathepsin D	89.38%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	88.88%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.81%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	88.44%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	88.37%	92.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.02%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.96%	94.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.01%	96.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.19%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.50%	95.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.19%	92.88%
CHEMBL259	P32245	Melanocortin receptor 4	85.05%	95.38%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.46%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	83.98%	91.19%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.86%	96.90%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.80%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.76%	96.09%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.67%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.48%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.16%	91.07%
CHEMBL1871	P10275	Androgen Receptor	82.10%	96.43%
CHEMBL1902	P62942	FK506-binding protein 1A	80.38%	97.05%
CHEMBL1951	P21397	Monoamine oxidase A	80.14%	91.49%

Plants that contains it

• Bellevalia paradoxa

Cross-Links

• PubChem: 163005642
• LOTUS: LTS0035956
• wikiData: Q105299040