O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate

Details

• Internal ID: a349dca5-6a5f-4bd9-b200-a71544ca5ca8
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-[4-[(methoxycarbonylamino)methyl]phenoxy]-2-methyloxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC=C(C=C2)CNC(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)CNC(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C21H27NO10/c1-11-17(29-12(2)23)18(30-13(3)24)19(31-14(4)25)20(28-11)32-16-8-6-15(7-9-16)10-22-21(26)27-5/h6-9,11,17-20H,10H2,1-5H3,(H,22,26)/t11-,17-,18+,19+,20-/m0/s1
• InChI Key: LCQPFOZNYVLABG-FXCHBBSNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₇NO₁₀
• Molecular Weight: 453.40 g/mol
• Exact Mass: 453.16349606 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.46
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• O-Methyl-4-[(2',3',4'-tri-O-acetyl-alpha-L-rhamnosyloxy)benzyl]carbamate
• [4-(2-O,3-O,4-O-Triacetyl-alpha-L-rhamnopyranosyloxy)benzyl]carbamic acid methyl ester
• 163812-18-8
• Carbamic acid, [[4-[(2,3,4-tri-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy]phenyl]methyl]-, methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9028	90.28%
Caco-2	-	0.5988	59.88%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5223	52.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8920	89.20%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7041	70.41%
P-glycoprotein inhibitior	+	0.7930	79.30%
P-glycoprotein substrate	-	0.7929	79.29%
CYP3A4 substrate	+	0.6039	60.39%
CYP2C9 substrate	-	0.6085	60.85%
CYP2D6 substrate	-	0.8779	87.79%
CYP3A4 inhibition	-	0.5615	56.15%
CYP2C9 inhibition	-	0.7851	78.51%
CYP2C19 inhibition	-	0.5116	51.16%
CYP2D6 inhibition	-	0.7966	79.66%
CYP1A2 inhibition	-	0.7381	73.81%
CYP2C8 inhibition	-	0.7285	72.85%
CYP inhibitory promiscuity	+	0.6333	63.33%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.5509	55.09%
Eye corrosion	-	0.9803	98.03%
Eye irritation	-	0.9466	94.66%
Skin irritation	-	0.8136	81.36%
Skin corrosion	-	0.9510	95.10%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7324	73.24%
Micronuclear	+	0.7459	74.59%
Hepatotoxicity	-	0.5984	59.84%
skin sensitisation	-	0.9165	91.65%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7950	79.50%
Acute Oral Toxicity (c)	III	0.4342	43.42%
Estrogen receptor binding	+	0.5864	58.64%
Androgen receptor binding	-	0.4936	49.36%
Thyroid receptor binding	+	0.6176	61.76%
Glucocorticoid receptor binding	+	0.5891	58.91%
Aromatase binding	-	0.6239	62.39%
PPAR gamma	-	0.5275	52.75%
Honey bee toxicity	-	0.7072	70.72%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.7371	73.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.00%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.67%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.53%	98.95%
CHEMBL4208	P20618	Proteasome component C5	92.53%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.17%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	89.90%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.95%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.78%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.65%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.93%	94.45%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.79%	81.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.10%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.88%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.86%	86.33%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.27%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.01%	95.56%

Plants that contains it

• Calamus draco
• Excoecaria acerifolia
• Garrya laurifolia
• Goupia glabra
• Laggera alata
• Medinilla magnifica
• Mesua ferrea
• Moringa oleifera
• Onobrychis bobrovii
• Papaver persicum
• Petteria ramentacea
• Senecio cathcartensis
• Sequoia sempervirens
• Syncarpha gnaphaloides

Cross-Links

• PubChem: 101919834
• NPASS: NPC199116
• LOTUS: LTS0117299
• wikiData: Q105149948