(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S)-2-[[(3S,4R,4aR,6aR,6bS,8R,8aS,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 5a9b4721-63d9-4a6b-b181-c25f0974b6be
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S)-2-[[(3S,4R,4aR,6aR,6bS,8R,8aS,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(CO8)O)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)CO)C
• SMILES (Isomeric): C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)CO)O)C)C)(C)CO)O[C@H]6[C@@H]([C@H]([C@H](CO6)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)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O
• InChI: InChI=1S/C52H86O22/c1-47(2)13-14-52(22-56)24(15-47)23-7-8-30-48(3)11-10-32(49(4,21-55)29(48)9-12-50(30,5)51(23,6)16-31(52)58)72-45-41(74-44-40(66)37(63)34(60)26(17-53)69-44)36(62)28(20-68-45)71-46-42(38(64)35(61)27(18-54)70-46)73-43-39(65)33(59)25(57)19-67-43/h7,24-46,53-66H,8-22H2,1-6H3/t24-,25-,26+,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,48-,49-,50+,51+,52+/m0/s1
• InChI Key: AIRVJEHJSLWBFB-KJWUCAOFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₆O₂₂
• Molecular Weight: 1063.20 g/mol
• Exact Mass: 1062.56107437 g/mol
• Topological Polar Surface Area (TPSA): 357.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -2.34
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7084	70.84%
Caco-2	-	0.8919	89.19%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7876	78.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8214	82.14%
OATP1B3 inhibitior	-	0.4367	43.67%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.8267	82.67%
P-glycoprotein inhibitior	+	0.7432	74.32%
P-glycoprotein substrate	-	0.5821	58.21%
CYP3A4 substrate	+	0.7403	74.03%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9345	93.45%
CYP2C9 inhibition	-	0.8819	88.19%
CYP2C19 inhibition	-	0.8988	89.88%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.8923	89.23%
CYP2C8 inhibition	+	0.7227	72.27%
CYP inhibitory promiscuity	-	0.9600	96.00%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6252	62.52%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9046	90.46%
Skin irritation	-	0.6425	64.25%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7818	78.18%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7302	73.02%
skin sensitisation	-	0.8896	88.96%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.8178	81.78%
Acute Oral Toxicity (c)	III	0.7434	74.34%
Estrogen receptor binding	+	0.8106	81.06%
Androgen receptor binding	+	0.7415	74.15%
Thyroid receptor binding	-	0.5295	52.95%
Glucocorticoid receptor binding	+	0.6703	67.03%
Aromatase binding	+	0.6399	63.99%
PPAR gamma	+	0.7757	77.57%
Honey bee toxicity	-	0.6647	66.47%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9174	91.74%

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	96.21%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.75%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.87%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.66%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	90.28%	90.17%
CHEMBL1937	Q92769	Histone deacetylase 2	88.06%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.94%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.42%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	86.92%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.46%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.15%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.68%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.05%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.80%	96.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.70%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.97%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.36%	92.62%

Plants that contains it

• Lysimachia heterogenea

Cross-Links

• PubChem: 163187657
• LOTUS: LTS0129466
• wikiData: Q104912945