Ketologanic acid

Details

• Internal ID: ef768545-6d0b-4f8b-b472-c8232411f781
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7R,7aS)-7-methyl-6-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• InChI: InChI=1S/C16H22O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,9-13,15-17,19-21H,2-3H2,1H3,(H,22,23)/t5-,6+,9+,10+,11+,12-,13+,15-,16-/m0/s1
• InChI Key: HGYUBLMQZDQRSI-PZGZDOIQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₀
• Molecular Weight: 374.34 g/mol
• Exact Mass: 374.12129689 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.03
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• Ketologanic acid
• SCHEMBL29425939
• DTXSID601106233
• (1S,4aS,7R,7aS)-1-(I(2)-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-6-oxocyclopenta[c]pyran-4-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6397	63.97%
Caco-2	-	0.9067	90.67%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7287	72.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3802	38.02%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8470	84.70%
P-glycoprotein inhibitior	-	0.8981	89.81%
P-glycoprotein substrate	-	0.8890	88.90%
CYP3A4 substrate	+	0.5274	52.74%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.8845	88.45%
CYP3A4 inhibition	-	0.9336	93.36%
CYP2C9 inhibition	-	0.8768	87.68%
CYP2C19 inhibition	-	0.9029	90.29%
CYP2D6 inhibition	-	0.9275	92.75%
CYP1A2 inhibition	-	0.8467	84.67%
CYP2C8 inhibition	-	0.8147	81.47%
CYP inhibitory promiscuity	-	0.8027	80.27%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7101	71.01%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9460	94.60%
Skin irritation	-	0.7278	72.78%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.5747	57.47%
Human Ether-a-go-go-Related Gene inhibition	-	0.6082	60.82%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.7089	70.89%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4776	47.76%
Acute Oral Toxicity (c)	III	0.4959	49.59%
Estrogen receptor binding	+	0.6310	63.10%
Androgen receptor binding	-	0.5293	52.93%
Thyroid receptor binding	-	0.5564	55.64%
Glucocorticoid receptor binding	-	0.5066	50.66%
Aromatase binding	-	0.5315	53.15%
PPAR gamma	-	0.6069	60.69%
Honey bee toxicity	-	0.8980	89.80%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7350	73.50%
Fish aquatic toxicity	+	0.8133	81.33%

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	95.98%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.93%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.33%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.90%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.23%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.03%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.17%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	83.28%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	81.44%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.20%	86.92%
CHEMBL4208	P20618	Proteasome component C5	80.14%	90.00%

Plants that contains it

• Picconia excelsa

Cross-Links

• PubChem: 14137244
• LOTUS: LTS0007782
• wikiData: Q105028088