11-Methylforsythide

Details

• Internal ID: 8f2d5762-8c9d-40dd-9f32-5ed83fbf3bd4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7S,7aS)-4-methoxycarbonyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-carboxylic acid
• SMILES (Canonical): COC(=O)C1=COC(C2C1CCC2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC[C@@H]2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C17H24O11/c1-25-15(24)8-5-26-16(10-6(8)2-3-7(10)14(22)23)28-17-13(21)12(20)11(19)9(4-18)27-17/h5-7,9-13,16-21H,2-4H2,1H3,(H,22,23)/t6-,7+,9-,10+,11-,12+,13-,16+,17+/m1/s1
• InChI Key: RLCWEUBIDIWNEA-JACXBSBZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.06
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• MEGxp0_000630
• ACon1_000329
• AKOS040763277
• NCGC00169180-01
• NCGC00169180-03
• 159598-00-2
• NCGC00169180-03_C17H24O11_Cyclopenta[c]pyran-4,7-dicarboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-, 4-methyl ester, (1S,4aS,7S,7aS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5277	52.77%
Caco-2	-	0.8877	88.77%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7756	77.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7142	71.42%
OATP1B3 inhibitior	+	0.9658	96.58%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9385	93.85%
P-glycoprotein inhibitior	-	0.8716	87.16%
P-glycoprotein substrate	-	0.8446	84.46%
CYP3A4 substrate	+	0.6006	60.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8739	87.39%
CYP3A4 inhibition	-	0.9435	94.35%
CYP2C9 inhibition	-	0.8551	85.51%
CYP2C19 inhibition	-	0.8663	86.63%
CYP2D6 inhibition	-	0.9049	90.49%
CYP1A2 inhibition	-	0.8463	84.63%
CYP2C8 inhibition	-	0.6005	60.05%
CYP inhibitory promiscuity	-	0.8337	83.37%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6518	65.18%
Eye corrosion	-	0.9846	98.46%
Eye irritation	-	0.9517	95.17%
Skin irritation	-	0.7685	76.85%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5984	59.84%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8913	89.13%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5469	54.69%
Acute Oral Toxicity (c)	III	0.5039	50.39%
Estrogen receptor binding	+	0.6133	61.33%
Androgen receptor binding	+	0.5650	56.50%
Thyroid receptor binding	-	0.6159	61.59%
Glucocorticoid receptor binding	-	0.6959	69.59%
Aromatase binding	-	0.6887	68.87%
PPAR gamma	-	0.5684	56.84%
Honey bee toxicity	-	0.9031	90.31%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.6018	60.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.31%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.39%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.47%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	86.47%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.15%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	85.89%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.79%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.20%	85.14%
CHEMBL2581	P07339	Cathepsin D	81.17%	98.95%
CHEMBL5028	O14672	ADAM10	80.38%	97.50%

Plants that contains it

• Forsythia europaea

Cross-Links

• PubChem: 23928114
• LOTUS: LTS0118528
• wikiData: Q105239819