Genipin 1-gentiobioside

Details

• Internal ID: 767e5e59-fde4-4146-a443-9d310873bff6
• 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-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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)COC4C(C(C(C(O4)CO)O)O)O)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[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C23H34O15/c1-33-20(32)10-6-34-21(13-8(4-24)2-3-9(10)13)38-23-19(31)17(29)15(27)12(37-23)7-35-22-18(30)16(28)14(26)11(5-25)36-22/h2,6,9,11-19,21-31H,3-5,7H2,1H3/t9-,11-,12-,13-,14-,15-,16+,17+,18-,19-,21+,22-,23+/m1/s1
• InChI Key: FYZYXYLPBWLLGI-AUOPOVQUSA-N
• Popularity: 11 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: -4.50
• Atomic LogP (AlogP): -4.40
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• 29307-60-6
• genipin gentiobioside
• GBGB
• genipin-1-b-D-gentiobioside
• Genipin 1-beta-gentiobioside
• Genipin 1-o-beta-D-gentiobioside
• UNII-0NI5399RDZ
• Genipin 1-|A-D-gentiobioside
• 0NI5399RDZ
• methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• CHEBI:80829
• Genipin 1-beta-D-gentiobioside
• Genipingentiobioside
• Genipin-gentiobioside
• C23H34O15
• Genipin 1-b-gentiobioside
• Genipin 1--D-gentiobioside
• Genipin 1-b-D-gentiobioside
• CHEMBL504969
• DTXSID50183554
• GENIPIN 1-O-GENTIOBIOSIDE
• HY-N2094
• MFCD12031626
• s3270
• AKOS032946013
• GENIPIN 1-.BETA.-GENTIOBIOSIDE
• C23-H34-O15
• NCGC00347524-02
• AC-34358
• GENIPIN 1-.BETA.-D-GENTIOBIOSIDE
• MS-30068
• GENIPIN 1-O-.BETA.-D-GENTIOBIOSIDE
• CS-0018599
• C16965
• F17696
• A924149
• Q27149871
• Genipin 1-gentiobioside; Genipin 1--gentiobioside; Genipin gentiobioside
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-((6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-1,4A,5,7A-TETRAHYDRO-7-(HYDROXYMETHYL)-, METHYL ESTER, (1S,4AS,7AS)-
• Cyclopenta(c)pyran-4-carboxylic acid, 1-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1R-(1alpha,4aalpha,7aalpha))-
• Methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-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	-	0.8913	89.13%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7455	74.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7992	79.92%
OATP1B3 inhibitior	+	0.9654	96.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6939	69.39%
P-glycoprotein inhibitior	-	0.7220	72.20%
P-glycoprotein substrate	-	0.7138	71.38%
CYP3A4 substrate	+	0.6362	63.62%
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	-	0.5960	59.60%
CYP inhibitory promiscuity	-	0.8142	81.42%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6981	69.81%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.8095	80.95%
Skin corrosion	-	0.9587	95.87%
Ames mutagenesis	-	0.5891	58.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.6561	65.61%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7625	76.25%
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	+	0.8114	81.14%
Acute Oral Toxicity (c)	III	0.4591	45.91%
Estrogen receptor binding	+	0.7217	72.17%
Androgen receptor binding	+	0.5577	55.77%
Thyroid receptor binding	-	0.5853	58.53%
Glucocorticoid receptor binding	-	0.5299	52.99%
Aromatase binding	+	0.6197	61.97%
PPAR gamma	+	0.6013	60.13%
Honey bee toxicity	-	0.8326	83.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
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	97.19%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.05%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.34%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	87.76%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	86.31%	92.50%
CHEMBL2581	P07339	Cathepsin D	85.14%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.84%	96.61%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.58%	96.00%
CHEMBL5028	O14672	ADAM10	82.68%	97.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.44%	86.92%
CHEMBL4208	P20618	Proteasome component C5	82.05%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.84%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.38%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	80.33%	95.93%

Plants that contains it

• Eucommia ulmoides
• Gardenia jasminoides
• Genipa americana

Cross-Links

• PubChem: 3082301
• NPASS: NPC118761
• LOTUS: LTS0080747
• wikiData: Q27149871