[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aS,14bS)-2-acetyloxy-10-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: fbb55dcd-318c-4f2f-82bd-6be8c5b7f5d4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aS,14bS)-2-acetyloxy-10-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC(=O)OC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(C(O6)CO)O)OC7C(C(C(C(O7)CO)O)O)O)O)C)C)C2C1)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C
• SMILES (Isomeric): CC(=O)O[C@]1(CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[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)O)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)O)C)C)[C@@H]2C1)C)C(=O)O[C@@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C
• InChI: InChI=1S/C49H78O21/c1-22(54)70-44(2)13-15-49(43(63)69-41-37(61)35(59)32(56)26(19-51)65-41)16-14-47(5)23(24(49)17-44)7-8-29-45(3)11-10-30(46(4,21-53)28(45)9-12-48(29,47)6)67-42-38(62)39(33(57)27(20-52)66-42)68-40-36(60)34(58)31(55)25(18-50)64-40/h7,24-42,50-53,55-62H,8-21H2,1-6H3/t24-,25+,26+,27+,28+,29+,30-,31-,32+,33+,34-,35-,36+,37+,38+,39-,40-,41+,42+,44-,45+,46-,47+,48+,49-/m0/s1
• InChI Key: TWOOQDFOZFJIQT-NPOATVFMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₈O₂₁
• Molecular Weight: 1003.10 g/mol
• Exact Mass: 1002.50355949 g/mol
• Topological Polar Surface Area (TPSA): 342.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.59
• H-Bond Acceptor: 21
• 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	+	0.6512	65.12%
Caco-2	-	0.8803	88.03%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8681	86.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8322	83.22%
OATP1B3 inhibitior	-	0.3733	37.33%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5452	54.52%
BSEP inhibitior	+	0.8641	86.41%
P-glycoprotein inhibitior	+	0.7475	74.75%
P-glycoprotein substrate	-	0.6474	64.74%
CYP3A4 substrate	+	0.7238	72.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8774	87.74%
CYP3A4 inhibition	-	0.9116	91.16%
CYP2C9 inhibition	-	0.9240	92.40%
CYP2C19 inhibition	-	0.9287	92.87%
CYP2D6 inhibition	-	0.9557	95.57%
CYP1A2 inhibition	-	0.8761	87.61%
CYP2C8 inhibition	+	0.7248	72.48%
CYP inhibitory promiscuity	-	0.9598	95.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9027	90.27%
Skin irritation	-	0.5790	57.90%
Skin corrosion	-	0.9471	94.71%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7950	79.50%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8111	81.11%
skin sensitisation	-	0.9261	92.61%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.5189	51.89%
Acute Oral Toxicity (c)	III	0.6932	69.32%
Estrogen receptor binding	+	0.7870	78.70%
Androgen receptor binding	+	0.7491	74.91%
Thyroid receptor binding	-	0.5277	52.77%
Glucocorticoid receptor binding	+	0.7377	73.77%
Aromatase binding	+	0.6141	61.41%
PPAR gamma	+	0.7973	79.73%
Honey bee toxicity	-	0.7012	70.12%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9625	96.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.90%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.89%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.65%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.08%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.46%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.83%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.11%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.99%	94.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.46%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.93%	97.36%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.90%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.73%	95.56%
CHEMBL2581	P07339	Cathepsin D	82.00%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.01%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	80.70%	92.50%
CHEMBL5028	O14672	ADAM10	80.54%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.03%	99.17%

Plants that contains it

• Chenopodium quinoa

Cross-Links

• PubChem: 163106097
• LOTUS: LTS0171676
• wikiData: Q105265953