10-O-Acetylgeniposidic acid

Details

• Internal ID: 0892967f-bb0c-405e-9921-16c139bcf7be
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (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-carboxylic acid
• SMILES (Canonical): CC(=O)OCC1=CCC2C1C(OC=C2C(=O)O)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)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C18H24O11/c1-7(20)26-5-8-2-3-9-10(16(24)25)6-27-17(12(8)9)29-18-15(23)14(22)13(21)11(4-19)28-18/h2,6,9,11-15,17-19,21-23H,3-5H2,1H3,(H,24,25)/t9-,11-,12-,13-,14+,15-,17+,18+/m1/s1
• InChI Key: GJCLXUNGVGZROH-IHSYADGBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₁₁
• Molecular Weight: 416.40 g/mol
• Exact Mass: 416.13186158 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -1.75
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5886	58.86%
Caco-2	-	0.8913	89.13%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7932	79.32%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.7469	74.69%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6277	62.77%
P-glycoprotein inhibitior	-	0.8450	84.50%
P-glycoprotein substrate	-	0.8523	85.23%
CYP3A4 substrate	+	0.5875	58.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8876	88.76%
CYP3A4 inhibition	-	0.9626	96.26%
CYP2C9 inhibition	-	0.9248	92.48%
CYP2C19 inhibition	-	0.8808	88.08%
CYP2D6 inhibition	-	0.9211	92.11%
CYP1A2 inhibition	-	0.8612	86.12%
CYP2C8 inhibition	-	0.6624	66.24%
CYP inhibitory promiscuity	-	0.8863	88.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7358	73.58%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9403	94.03%
Skin irritation	-	0.7672	76.72%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5596	55.96%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.8199	81.99%
skin sensitisation	-	0.8951	89.51%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.8453	84.53%
Acute Oral Toxicity (c)	III	0.4211	42.11%
Estrogen receptor binding	+	0.6504	65.04%
Androgen receptor binding	+	0.6143	61.43%
Thyroid receptor binding	-	0.6108	61.08%
Glucocorticoid receptor binding	-	0.4697	46.97%
Aromatase binding	+	0.6162	61.62%
PPAR gamma	+	0.5625	56.25%
Honey bee toxicity	-	0.8298	82.98%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7950	79.50%
Fish aquatic toxicity	+	0.9366	93.66%

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	96.72%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.19%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.59%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.84%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.65%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.04%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.96%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.51%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.32%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.09%	95.56%

Plants that contains it

• Akebia quinata
• Caragana sinica
• Plantago alpina
• Scyphiphora hydrophylacea
• Tanacetum cinerariifolium

Cross-Links

• PubChem: 101996850
• NPASS: NPC210506
• LOTUS: LTS0116374
• wikiData: Q105009337