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

Details

• Internal ID: 40bc3348-5155-4ade-9a06-ae6ef29424cc
• 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,4R,5S)-4-acetyloxy-3-hydroxy-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)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@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)O)O)O)O
• InChI: InChI=1S/C48H76O17/c1-23-32(53)33(54)34(55)39(60-23)65-38-36(64-40-35(56)37(61-24(2)51)28(20-49)62-40)27(52)21-59-41(38)63-31-12-13-44(5)29(45(31,6)22-50)11-14-47(8)30(44)10-9-25-26-19-43(3,4)15-17-48(26,42(57)58)18-16-46(25,47)7/h9,23,26-41,49-50,52-56H,10-22H2,1-8H3,(H,57,58)/t23-,26-,27-,28-,29+,30+,31-,32-,33+,34+,35+,36-,37-,38+,39-,40-,41+,44-,45-,46+,47+,48-/m0/s1
• InChI Key: DNKHPELVBNJAOP-HKNYIALVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₆O₁₇
• Molecular Weight: 925.10 g/mol
• Exact Mass: 924.50825095 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 10

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	-	0.8868	88.68%
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	+	0.7849	78.49%
OATP1B3 inhibitior	+	0.8381	83.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.7000	70.00%
P-glycoprotein inhibitior	+	0.7598	75.98%
P-glycoprotein substrate	-	0.5139	51.39%
CYP3A4 substrate	+	0.7355	73.55%
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	+	0.7107	71.07%
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	-	0.9060	90.60%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6458	64.58%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6296	62.96%
Acute Oral Toxicity (c)	III	0.6742	67.42%
Estrogen receptor binding	+	0.7972	79.72%
Androgen receptor binding	+	0.7316	73.16%
Thyroid receptor binding	-	0.5897	58.97%
Glucocorticoid receptor binding	+	0.7241	72.41%
Aromatase binding	+	0.6734	67.34%
PPAR gamma	+	0.7938	79.38%
Honey bee toxicity	-	0.6786	67.86%
Biodegradation	-	0.7500	75.00%
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	97.99%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.44%	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	91.18%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.10%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.85%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.16%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.03%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.26%	98.95%
CHEMBL5028	O14672	ADAM10	83.71%	97.50%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.92%	89.44%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.71%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.68%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.73%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.18%	91.19%

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: 53483550
• NPASS: NPC88768