6-Hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 4c13c2b6-546d-4928-890d-4d2c3e589819
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• InChI: InChI=1S/C16H24O10/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/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)
• InChI Key: JNNGEAWILNVFFD-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.36 g/mol
• Exact Mass: 376.13694696 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.24
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• Loganic acid (Not validated)
• CHEBI:181591
• 8-Methoxyquinoline-5-carboxylicacid
• 6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• FT-0777304

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7275	72.75%
Caco-2	-	0.8903	89.03%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6384	63.84%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	-	0.7737	77.37%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9340	93.40%
P-glycoprotein inhibitior	-	0.9070	90.70%
P-glycoprotein substrate	-	0.8694	86.94%
CYP3A4 substrate	+	0.5444	54.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.9398	93.98%
CYP2C9 inhibition	-	0.9222	92.22%
CYP2C19 inhibition	-	0.9125	91.25%
CYP2D6 inhibition	-	0.9058	90.58%
CYP1A2 inhibition	-	0.8383	83.83%
CYP2C8 inhibition	-	0.7895	78.95%
CYP inhibitory promiscuity	-	0.8323	83.23%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7232	72.32%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9601	96.01%
Skin irritation	-	0.7151	71.51%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.5747	57.47%
Human Ether-a-go-go-Related Gene inhibition	-	0.5798	57.98%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7714	77.14%
skin sensitisation	-	0.8822	88.22%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7727	77.27%
Acute Oral Toxicity (c)	III	0.4815	48.15%
Estrogen receptor binding	+	0.5361	53.61%
Androgen receptor binding	-	0.5663	56.63%
Thyroid receptor binding	+	0.5505	55.05%
Glucocorticoid receptor binding	-	0.5314	53.14%
Aromatase binding	+	0.5568	55.68%
PPAR gamma	-	0.4837	48.37%
Honey bee toxicity	-	0.8879	88.79%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.6666	66.66%

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	96.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.68%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.70%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	87.70%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.59%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.44%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.49%	99.17%
CHEMBL4208	P20618	Proteasome component C5	85.22%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.90%	97.25%
CHEMBL2581	P07339	Cathepsin D	83.57%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.62%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.57%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.48%	95.56%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.16%	95.71%

Plants that contains it

• Alangium chinense
• Alangium platanifolium
• Alangium premnifolium
• Cephalanthus occidentalis
• Cephalaria procera
• Dipsacus inermis
• Fagraea auriculata
• Gentiana dahurica
• Gentiana macrophylla
• Gentiana tibetica
• Gentiana triflora
• Ixanthus viscosus
• Lippia origanoides
• Lonicera periclymenum
• Ophiorrhiza kuroiwai
• Patrinia scabra
• Pedicularis longiflora
• Pedicularis torta
• Pedicularis verticillata
• Physostegia virginiana
• Physostegia virginiana subsp. virginiana
• Picconia excelsa
• Plantago alpina
• Plantago arborescens
• Plantago hookeriana
• Scutellaria albida
• Strychnos axillaris
• Strychnos cocculoides
• Strychnos lucida
• Strychnos nux-vomica
• Triaenophora rupestris
• Veronica longifolia

Cross-Links

• PubChem: 4430509
• LOTUS: LTS0241926
• wikiData: Q105132022