3beta-[[2-O-(alpha-L-Rhamnopyranosyl)-3-O-(2-O,3-O-diacetyl-alpha-L-arabinofuranosyl)-beta-L-arabinopyranosyl]oxy]-23-hydroxyoleana-12-ene-28-oic acid

Details

• Internal ID: dc5a18ba-cb65-49ec-b8d4-8c45ebd8b31f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2R,3R,4S,5S)-4-[(2S,3R,4S,5S)-3,4-diacetyloxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-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)OC8C(C(C(O8)CO)OC(=O)C)OC(=O)C)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@H]([C@]3(C)CO)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O)C)C)C)O)O[C@H]8[C@@H]([C@H]([C@@H](O8)CO)OC(=O)C)OC(=O)C)O)O)O
• InChI: InChI=1S/C50H78O18/c1-24-34(56)35(57)36(58)41(62-24)68-39-37(67-43-40(64-26(3)54)38(63-25(2)53)30(21-51)65-43)29(55)22-61-42(39)66-33-13-14-46(6)31(47(33,7)23-52)12-15-49(9)32(46)11-10-27-28-20-45(4,5)16-18-50(28,44(59)60)19-17-48(27,49)8/h10,24,28-43,51-52,55-58H,11-23H2,1-9H3,(H,59,60)/t24-,28-,29-,30-,31+,32+,33-,34-,35+,36+,37-,38-,39+,40+,41-,42+,43-,46-,47-,48+,49+,50-/m0/s1
• InChI Key: NQZJUEANUWEVDA-QHCSWDGBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₈O₁₈
• Molecular Weight: 967.10 g/mol
• Exact Mass: 966.51881563 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.13
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8427	84.27%
Caco-2	-	0.8784	87.84%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8733	87.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7894	78.94%
OATP1B3 inhibitior	+	0.8381	83.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.8595	85.95%
P-glycoprotein inhibitior	+	0.7586	75.86%
P-glycoprotein substrate	-	0.5284	52.84%
CYP3A4 substrate	+	0.7368	73.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.8187	81.87%
CYP2C9 inhibition	-	0.8372	83.72%
CYP2C19 inhibition	-	0.9259	92.59%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9133	91.33%
CYP2C8 inhibition	+	0.7261	72.61%
CYP inhibitory promiscuity	-	0.9476	94.76%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4689	46.89%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9033	90.33%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3991	39.91%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5805	58.05%
Acute Oral Toxicity (c)	III	0.6742	67.42%
Estrogen receptor binding	+	0.7969	79.69%
Androgen receptor binding	+	0.7347	73.47%
Thyroid receptor binding	-	0.5412	54.12%
Glucocorticoid receptor binding	+	0.7694	76.94%
Aromatase binding	+	0.6693	66.93%
PPAR gamma	+	0.8118	81.18%
Honey bee toxicity	-	0.6698	66.98%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9692	96.92%

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	97.36%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.36%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.71%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.46%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.04%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.85%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.37%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.16%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.31%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.44%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.83%	95.89%
CHEMBL5028	O14672	ADAM10	82.26%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.13%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.94%	94.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.49%	89.44%
CHEMBL340	P08684	Cytochrome P450 3A4	81.29%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.20%	95.50%

Plants that contains it

• Actiniopteris australis
• Canarium album
• Clematis hexapetala
• Ilex hainanensis
• Melicope durifolia
• Morus rubra
• Nephelium lappaceum
• Plinia cauliflora
• Sideritis nutans
• Stenomesson miniatum
• Uncaria guianensis
• Xylopia brasiliensis

Cross-Links

• PubChem: 53483549
• NPASS: NPC10564