3beta-[2-O-(3-O-alpha-L-Arabinopyranosyl-alpha-L-rhamnopyranosyl)-alpha-L-arabinopyranosyloxy]-23-hydroxyoleana-12-ene-28-oic acid

Details

• Internal ID: cabc8925-0bef-4047-b650-18ab8ef5b7f9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-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)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)O)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)O
• InChI: InChI=1S/C46H74O16/c1-22-30(50)35(61-37-33(53)31(51)25(48)19-57-37)34(54)38(59-22)62-36-32(52)26(49)20-58-39(36)60-29-11-12-42(4)27(43(29,5)21-47)10-13-45(7)28(42)9-8-23-24-18-41(2,3)14-16-46(24,40(55)56)17-15-44(23,45)6/h8,22,24-39,47-54H,9-21H2,1-7H3,(H,55,56)/t22-,24-,25-,26-,27+,28+,29-,30-,31-,32-,33+,34+,35+,36+,37-,38-,39-,42-,43-,44+,45+,46-/m0/s1
• InChI Key: IAGSHEHQJJTLLR-UXDKCJHBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₇₄O₁₆
• Molecular Weight: 883.10 g/mol
• Exact Mass: 882.49768627 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• 3beta-[2-O-(3-O-alpha-L-Arabinopyranosyl-alpha-L-rhamnopyranosyl)-alpha-L-arabinopyranosyloxy]-23-hydroxyoleana-12-ene-28-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8892	88.92%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	0.8797	87.97%
OATP1B1 inhibitior	+	0.8124	81.24%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.7997	79.97%
P-glycoprotein inhibitior	+	0.7524	75.24%
P-glycoprotein substrate	-	0.5645	56.45%
CYP3A4 substrate	+	0.7223	72.23%
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	+	0.6854	68.54%
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	-	0.9099	90.99%
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	+	0.6873	68.73%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.7169	71.69%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7914	79.14%
Androgen receptor binding	+	0.7343	73.43%
Thyroid receptor binding	-	0.5920	59.20%
Glucocorticoid receptor binding	+	0.6844	68.44%
Aromatase binding	+	0.6689	66.89%
PPAR gamma	+	0.7722	77.22%
Honey bee toxicity	-	0.7632	76.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5750	57.50%
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	97.21%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.76%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.65%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.75%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.93%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.42%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.13%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.38%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.96%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.17%	91.07%
CHEMBL5028	O14672	ADAM10	83.27%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.07%	95.89%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.13%	92.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.35%	90.71%

Plants that contains it

• Actiniopteris australis
• Arisaema erubescens
• Canarium album
• Clematis hexapetala
• Elattostachys apetala
• Eleutherococcus sieboldianus
• Ilex hainanensis
• Melicope durifolia
• Morus rubra
• Nephelium lappaceum
• Plinia cauliflora
• Sapindus mukorossi
• Sapindus trifoliatus
• Sideritis nutans
• Stenomesson miniatum
• Uncaria guianensis
• Xylopia brasiliensis

Cross-Links

• PubChem: 21637697
• NPASS: NPC27230
• LOTUS: LTS0049824
• wikiData: Q105036103