Geniposide

Details

• 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
• 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: 1,155 references in papers

Physical and Chemical Properties

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

Synonyms

• 24512-63-8
• 145295QLXY
• DTXSID101318419
• 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,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,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
• methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• RefChem:37139
• DTXCID701748230
• methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-4-carboxylate
• Jasminoidin
• 169799-41-1
• MFCD16036219
• CHEBI:5299
• 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
• 27745-20-6
• (1S,4aS,7aS)-Methyl 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
• UNII-145295QLXY
• Cyclopenta[c]pyran-4-carboxylic acid, 1-(ss-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-; Cyclopenta[c]pyran-4-carboxylic acid, 1-(ss-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, [1S-(1a,4aa,7aa)]-; Geniposide (8CI)
• CHEMBL462894
• orb1306089
• orb1696869
• Geniposide, >=98% (HPLC)
• SCHEMBL28006822
• GLXC-06546
• HMS3884F17
• Methyl (1S)-1alpha-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c]pyran-4-carboxylate
• MSK40032
• BDBM50478840
• s2411
• AKOS025311228
• CCG-268498
• MG09208
• NCGC00346662-04
• NCGC00346662-06
• SY074418
• NS00097664
• C09781
• W-5601
• AB01558902_03
• F807856
• BRD-K57275767-001-02-4
• BRD-K57275767-001-03-2
• Q27106709
• (1S)-1alpha-(beta-D-Glucopyranosyloxy)-7-(hydroxymethyl)-1,4aalpha,5,7aalpha-tetrahydrocyclopenta[c]pyran-4-carboxylic Acid Methyl Ester
• (1S,4aS,7aS)- 1-(ss-D-Glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)- cyclopenta[c]pyran-4-carboxylic acid methyl ester
• (1S,4aS,7aS)-1-(beta-D-Glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-cyclopenta[c]pyran-4-carboxylic acid methyl ester
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)- 1,4A,5,7A-TETRAHYDRO-7-(HYDROXYMETHYL)-, METHYL ESTER, (1S,4AS,7AS)-
• Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S-(1alpha,4aalpha,7aalpha))-
• Cyclopenta[c]pyran-4-carboxylic acid, 1-(|A-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7aS)-
• 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

2D Structure

ADMET Properties (via admetSAR 2)

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

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	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

• Aloysia citrodora
• Arbutus unedo
• Avicennia marina
• Biebersteinia heterostemon
• Cordiera sessilis
• Cordylanthus capitatus
• Cornus officinalis
• Escallonia myrtoidea
• Eucommia ulmoides
• Feretia apodanthera
• Gardenia jasminoides
• Garrya elliptica
• Genipa americana
• Globularia davisiana
• Globularia orientalis
• Lantana camara
• Lippia alba
• Paederia foetida
• Paratinospora sagittata
• Penstemon centranthifolius
• Penstemon crandallii
• Penstemon eximius
• Petasites japonicus
• Physostegia virginiana
• Plantago asiatica
• Plantago depressa
• Plocama calabrica
• Randia armata
• Rothmannia globosa
• Scrophularia nodosa
• Stigmaphyllon palmatum

Cross-Links

• PubChem: 107848
• NPASS: NPC255677
• LOTUS: LTS0099201
• wikiData: Q27106709