10-O-Acetylgeniposide

Details

• Internal ID: a95304a4-6f93-4fb6-ad39-7f9e0d4b7cba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,7aS)-7-(acetyloxymethyl)-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): CC(=O)OCC1=CCC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC(=O)OCC1=CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C19H26O11/c1-8(21)27-6-9-3-4-10-11(17(25)26-2)7-28-18(13(9)10)30-19-16(24)15(23)14(22)12(5-20)29-19/h3,7,10,12-16,18-20,22-24H,4-6H2,1-2H3/t10-,12-,13-,14-,15+,16-,18+,19+/m1/s1
• InChI Key: LOXQKSBAJJTUOX-BZDYRZRUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₁₁
• Molecular Weight: 430.40 g/mol
• Exact Mass: 430.14751164 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.66
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• 10-Acetylgenipiside
• CHEMBL1078435

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5811	58.11%
Caco-2	-	0.8468	84.68%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7538	75.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7871	78.71%
OATP1B3 inhibitior	+	0.9597	95.97%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5513	55.13%
P-glycoprotein inhibitior	-	0.7819	78.19%
P-glycoprotein substrate	-	0.7495	74.95%
CYP3A4 substrate	+	0.6435	64.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8859	88.59%
CYP3A4 inhibition	-	0.9396	93.96%
CYP2C9 inhibition	-	0.9369	93.69%
CYP2C19 inhibition	-	0.8898	88.98%
CYP2D6 inhibition	-	0.9180	91.80%
CYP1A2 inhibition	-	0.8928	89.28%
CYP2C8 inhibition	-	0.5680	56.80%
CYP inhibitory promiscuity	-	0.9038	90.38%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7518	75.18%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9436	94.36%
Skin irritation	-	0.7739	77.39%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3961	39.61%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.7949	79.49%
skin sensitisation	-	0.8871	88.71%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.8918	89.18%
Acute Oral Toxicity (c)	III	0.4274	42.74%
Estrogen receptor binding	+	0.7363	73.63%
Androgen receptor binding	+	0.6076	60.76%
Thyroid receptor binding	-	0.5958	59.58%
Glucocorticoid receptor binding	-	0.4915	49.15%
Aromatase binding	+	0.5276	52.76%
PPAR gamma	+	0.5198	51.98%
Honey bee toxicity	-	0.7900	79.00%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9000	90.00%

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	97.71%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.39%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.70%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.54%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.95%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.64%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.08%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.31%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.20%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.55%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	80.34%	91.19%

Plants that contains it

• Gardenia jasminoides

Cross-Links

• PubChem: 6324916
• NPASS: NPC211593
• LOTUS: LTS0213974
• wikiData: Q104400909