Melittoside

Details

• Internal ID: cad16605-e25f-46c4-92c6-6f95cc9ac35a
• 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)-5-hydroxy-7-(hydroxymethyl)-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C1=CO[C@H]([C@H]2[C@@]1([C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C21H32O15/c22-4-7-3-10(25)21(36-20-17(31)15(29)13(27)9(6-24)34-20)1-2-32-18(11(7)21)35-19-16(30)14(28)12(26)8(5-23)33-19/h1-3,8-20,22-31H,4-6H2/t8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18+,19+,20+,21-/m1/s1
• InChI Key: LZKBAGSBRBMVBE-GVKBFFPQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₁₅
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.17412031 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: -5.70
• Atomic LogP (AlogP): -5.86
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

• 19467-03-9
• (2S,3R,4S,5S,6R)-2-[[(1S,4aS,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CHEMBL3810093
• DTXSID101318140
• HY-N0915
• MFCD28964040
• AC-34524
• MS-29706
• (2S,3R,4S,5S,6R)-2-{[(1S,4aS,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4a-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6662	66.62%
Caco-2	-	0.8847	88.47%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6150	61.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8635	86.35%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9524	95.24%
P-glycoprotein inhibitior	-	0.7124	71.24%
P-glycoprotein substrate	-	0.8128	81.28%
CYP3A4 substrate	+	0.5848	58.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8272	82.72%
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	-	0.6340	63.40%
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	-	0.9161	91.61%
Skin irritation	-	0.8037	80.37%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7046	70.46%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8678	86.78%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6422	64.22%
Acute Oral Toxicity (c)	IV	0.3443	34.43%
Estrogen receptor binding	+	0.5523	55.23%
Androgen receptor binding	+	0.5851	58.51%
Thyroid receptor binding	+	0.5372	53.72%
Glucocorticoid receptor binding	-	0.5859	58.59%
Aromatase binding	+	0.7320	73.20%
PPAR gamma	+	0.6180	61.80%
Honey bee toxicity	-	0.7351	73.51%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
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	97.40%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.83%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.46%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.89%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	83.90%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.66%	94.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.06%	95.83%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.93%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.61%	89.67%

Plants that contains it

• Campylanthus glaber
• Castilleja attenuata
• Castilleja sessiliflora
• Clerodendrum thomsoniae
• Plantago alpina
• Plantago loeflingii
• Plantago maritima
• Plantago media
• Rehmannia glutinosa
• Sideritis trojana
• Stachys grandidentata
• Stachys recta
• Veronica intercedens
• Volkameria inermis

Cross-Links

• PubChem: 11968737
• NPASS: NPC280390
• LOTUS: LTS0260659
• wikiData: Q104388389