(4aS,6bR,9S,10S,12aR)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: de28f673-8c9b-4878-9f92-6ee4079976c5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6bR,9S,10S,12aR)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)OC8C(C(C(CO8)OC9C(C(C(C(O9)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@]4(C([C@@]3(C)CO)CC[C@@]5(C4CC=C6C5(CC[C@@]7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O
• InChI: InChI=1S/C52H84O21/c1-23-32(56)40(72-42-37(61)35(59)28(21-67-42)70-43-38(62)36(60)34(58)27(19-53)69-43)39(63)44(68-23)73-41-33(57)26(55)20-66-45(41)71-31-11-12-48(4)29(49(31,5)22-54)10-13-51(7)30(48)9-8-24-25-18-47(2,3)14-16-52(25,46(64)65)17-15-50(24,51)6/h8,23,25-45,53-63H,9-22H2,1-7H3,(H,64,65)/t23-,25?,26-,27+,28+,29?,30?,31-,32-,33-,34+,35-,36-,37+,38+,39+,40+,41+,42-,43-,44-,45-,48-,49+,50?,51+,52-/m0/s1
• InChI Key: BECKQSNYULYJHB-RBLWTFERSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₄O₂₁
• Molecular Weight: 1045.20 g/mol
• Exact Mass: 1044.55050968 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.19
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8789	87.89%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8010	80.10%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.8935	89.35%
P-glycoprotein inhibitior	+	0.7470	74.70%
P-glycoprotein substrate	-	0.5119	51.19%
CYP3A4 substrate	+	0.7358	73.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7476	74.76%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9027	90.27%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7561	75.61%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8094	80.94%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8167	81.67%
Androgen receptor binding	+	0.7344	73.44%
Thyroid receptor binding	+	0.5170	51.70%
Glucocorticoid receptor binding	+	0.7214	72.14%
Aromatase binding	+	0.6776	67.76%
PPAR gamma	+	0.8106	81.06%
Honey bee toxicity	-	0.6841	68.41%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.9411	94.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.59%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.90%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.00%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.34%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.20%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.68%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.67%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	87.76%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.17%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.71%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.79%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.03%	95.89%
CHEMBL5028	O14672	ADAM10	83.99%	97.50%
CHEMBL2581	P07339	Cathepsin D	83.50%	98.95%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.64%	92.78%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.54%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.52%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.42%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.10%	100.00%

Plants that contains it

• Kalopanax septemlobus
• Lonicera macrantha
• Sapindus mukorossi

Cross-Links

• PubChem: 6325966
• NPASS: NPC150426
• LOTUS: LTS0215412
• wikiData: Q105100580