Genameside D

Details

• Internal ID: 1fc22059-1b2b-4680-9d86-4696c46999bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,7aS)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CC=C2COC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO[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/C23H34O15/c1-33-20(32)10-7-35-21(38-23-19(31)17(29)15(27)12(5-25)37-23)13-8(2-3-9(10)13)6-34-22-18(30)16(28)14(26)11(4-24)36-22/h2,7,9,11-19,21-31H,3-6H2,1H3/t9-,11-,12-,13-,14-,15-,16+,17+,18-,19-,21+,22-,23+/m1/s1
• InChI Key: BNXFBCBJALNHOV-AUOPOVQUSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₄O₁₅
• Molecular Weight: 550.50 g/mol
• Exact Mass: 550.18977037 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -4.40
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• CHEMBL2311861

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4730	47.30%
Caco-2	-	0.8923	89.23%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7455	74.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7967	79.67%
OATP1B3 inhibitior	+	0.9654	96.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6156	61.56%
P-glycoprotein inhibitior	-	0.6726	67.26%
P-glycoprotein substrate	-	0.7484	74.84%
CYP3A4 substrate	+	0.6227	62.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8572	85.72%
CYP3A4 inhibition	-	0.9613	96.13%
CYP2C9 inhibition	-	0.9352	93.52%
CYP2C19 inhibition	-	0.8331	83.31%
CYP2D6 inhibition	-	0.9035	90.35%
CYP1A2 inhibition	-	0.8879	88.79%
CYP2C8 inhibition	-	0.5741	57.41%
CYP inhibitory promiscuity	-	0.8142	81.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6981	69.81%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9388	93.88%
Skin irritation	-	0.8095	80.95%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.6337	63.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7946	79.46%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8808	88.08%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.8390	83.90%
Acute Oral Toxicity (c)	III	0.4591	45.91%
Estrogen receptor binding	+	0.7254	72.54%
Androgen receptor binding	+	0.6391	63.91%
Thyroid receptor binding	-	0.5648	56.48%
Glucocorticoid receptor binding	-	0.4689	46.89%
Aromatase binding	+	0.6494	64.94%
PPAR gamma	+	0.5217	52.17%
Honey bee toxicity	-	0.8166	81.66%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.7201	72.01%

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	97.10%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.90%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.32%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.21%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.65%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.04%	98.95%
CHEMBL4208	P20618	Proteasome component C5	83.62%	90.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.21%	92.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.61%	96.61%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.01%	96.95%

Plants that contains it

• Gardenia jasminoides
• Genipa americana

Cross-Links

• PubChem: 11570273
• NPASS: NPC222062
• LOTUS: LTS0249288
• wikiData: Q104939086