Geniposide

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	e7279db9-b283-46c2-b608-f2008b0882a5
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name	methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical)	COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O
SMILES (Isomeric)	COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI	InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1
InChI Key	IBFYXTRXDNAPMM-BVTMAQQCSA-N
Popularity	887 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₇H₂₄O₁₀
Molecular Weight	388.40 g/mol
Exact Mass	388.13694696 g/mol
Topological Polar Surface Area (TPSA)	155.00 Å²
XlogP	-2.30
Atomic LogP (AlogP)	-2.23
H-Bond Acceptor	10
H-Bond Donor	5
Rotatable Bonds	5

Synonyms

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24512-63-8

Jasminoidin

UNII-145295QLXY

CHEBI:5299

145295QLXY

169799-41-1

methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Cyclopenta[c]pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-

methyl (1S,4aS,7aR)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4730	47.30%
Caco-2	-	0.8505	85.05%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7455	74.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7891	78.91%
OATP1B3 inhibitior	+	0.9654	96.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9318	93.18%
P-glycoprotein inhibitior	-	0.9063	90.63%
P-glycoprotein substrate	-	0.7975	79.75%
CYP3A4 substrate	+	0.6068	60.68%
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	-	0.6906	69.06%
CYP inhibitory promiscuity	-	0.8142	81.42%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6981	69.81%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9594	95.94%
Skin irritation	-	0.8095	80.95%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.5537	55.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5653	56.53%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8808	88.08%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	III	0.4591	45.91%
Estrogen receptor binding	+	0.5689	56.89%
Androgen receptor binding	+	0.5354	53.54%
Thyroid receptor binding	-	0.6330	63.30%
Glucocorticoid receptor binding	-	0.5507	55.07%
Aromatase binding	+	0.5340	53.40%
PPAR gamma	-	0.5380	53.80%
Honey bee toxicity	-	0.8540	85.40%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.7201	72.01%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	96.88%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.51%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.48%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	86.29%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.36%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	83.69%	92.50%
CHEMBL4208	P20618	Proteasome component C5	82.81%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.31%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.92%	99.17%
CHEMBL5028	O14672	ADAM10	81.56%	97.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.29%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.24%	95.83%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Aloysia citrodora

Arbutus unedo

Avicennia marina

Biebersteinia heterostemon

Cordiera sessilis

Cordylanthus capitatus