Monomelittoside

Details

• Internal ID: 21ec6496-d4c1-4de6-ab58-78259e45b795
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,4aS,5R,7aR)-4a,5-dihydroxy-7-(hydroxymethyl)-5,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=COC(C2C1(C(C=C2CO)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=CO[C@H]([C@H]2[C@@]1([C@@H](C=C2CO)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C15H22O10/c16-4-6-3-8(18)15(22)1-2-23-13(9(6)15)25-14-12(21)11(20)10(19)7(5-17)24-14/h1-3,7-14,16-22H,4-5H2/t7-,8-,9+,10-,11+,12-,13+,14+,15-/m1/s1
• InChI Key: WVHRUHMGDQLMBZ-KRWIWSHESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.33 g/mol
• Exact Mass: 362.12129689 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -4.10
• Atomic LogP (AlogP): -3.69
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• Danmelittoside
• 20633-72-1
• SCHEMBL9058085
• (2S,3R,4S,5S,6R)-2-[[(1S,4aS,5R,7aR)-4a,5-dihydroxy-7-(hydroxymethyl)-5,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• HY-N0916
• (2S,3R,4S,5S,6R)-2-(((1S,4aS,5R,7aR)-4a,5-dihydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-{[(1S,4aS,5R,7aR)-4a,5-dihydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• beta-D-Glucopyranoside, (1S,4aS,5R,7aR)-1,4a,5,7a-tetrahydro-4a,5-dihydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6662	66.62%
Caco-2	-	0.8552	85.52%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6150	61.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8779	87.79%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9751	97.51%
P-glycoprotein inhibitior	-	0.8802	88.02%
P-glycoprotein substrate	-	0.8410	84.10%
CYP3A4 substrate	+	0.5709	57.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8373	83.73%
CYP3A4 inhibition	-	0.9562	95.62%
CYP2C9 inhibition	-	0.8919	89.19%
CYP2C19 inhibition	-	0.7590	75.90%
CYP2D6 inhibition	-	0.8909	89.09%
CYP1A2 inhibition	-	0.8741	87.41%
CYP2C8 inhibition	-	0.7142	71.42%
CYP inhibitory promiscuity	-	0.7281	72.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6177	61.77%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9461	94.61%
Skin irritation	-	0.8037	80.37%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5821	58.21%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8678	86.78%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6356	63.56%
Acute Oral Toxicity (c)	IV	0.3443	34.43%
Estrogen receptor binding	-	0.7092	70.92%
Androgen receptor binding	+	0.5481	54.81%
Thyroid receptor binding	+	0.5182	51.82%
Glucocorticoid receptor binding	-	0.6246	62.46%
Aromatase binding	+	0.6937	69.37%
PPAR gamma	+	0.5789	57.89%
Honey bee toxicity	-	0.7975	79.75%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	-	0.5652	56.52%

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	96.96%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	94.68%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.56%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.55%	86.92%

Plants that contains it

• Campylanthus glaber
• Plantago alpina
• Plantago media
• Plantago subulata
• Rehmannia glutinosa
• Stachys grandidentata
• Stachys lavandulifolia
• Volkameria inermis

Cross-Links

• PubChem: 11968396
• NPASS: NPC187521
• LOTUS: LTS0045361
• wikiData: Q104396276