(1R)-7,8,9-trihydroxy-3,5-dioxo-1,2-dihydrocyclopenta[c]isochromene-1-carboxylic acid

Details

• Internal ID: 979739dd-e0b0-4f2f-85ba-1318da7ec45c
• Taxonomy: Phenylpropanoids and polyketides > Isocoumarins and derivatives
• IUPAC Name: (1R)-7,8,9-trihydroxy-3,5-dioxo-1,2-dihydrocyclopenta[c]isochromene-1-carboxylic acid
• SMILES (Canonical): C1C(C2=C(C1=O)OC(=O)C3=CC(=C(C(=C32)O)O)O)C(=O)O
• SMILES (Isomeric): C1[C@H](C2=C(C1=O)OC(=O)C3=CC(=C(C(=C32)O)O)O)C(=O)O
• InChI: InChI=1S/C13H8O8/c14-5-2-4-7(10(17)9(5)16)8-3(12(18)19)1-6(15)11(8)21-13(4)20/h2-3,14,16-17H,1H2,(H,18,19)/t3-/m1/s1
• InChI Key: JFJWMFPFMLRLMI-GSVOUGTGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₈
• Molecular Weight: 292.20 g/mol
• Exact Mass: 292.02191721 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.66
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7732	77.32%
Caco-2	-	0.9404	94.04%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5578	55.78%
OATP2B1 inhibitior	-	0.6960	69.60%
OATP1B1 inhibitior	+	0.9104	91.04%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9438	94.38%
P-glycoprotein inhibitior	-	0.9748	97.48%
P-glycoprotein substrate	-	0.8714	87.14%
CYP3A4 substrate	-	0.5510	55.10%
CYP2C9 substrate	+	0.6460	64.60%
CYP2D6 substrate	-	0.8558	85.58%
CYP3A4 inhibition	-	0.8490	84.90%
CYP2C9 inhibition	-	0.8940	89.40%
CYP2C19 inhibition	-	0.8671	86.71%
CYP2D6 inhibition	-	0.9589	95.89%
CYP1A2 inhibition	-	0.7678	76.78%
CYP2C8 inhibition	-	0.6119	61.19%
CYP inhibitory promiscuity	-	0.9608	96.08%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6466	64.66%
Eye corrosion	-	0.9913	99.13%
Eye irritation	+	0.8481	84.81%
Skin irritation	-	0.5677	56.77%
Skin corrosion	-	0.9364	93.64%
Ames mutagenesis	-	0.5634	56.34%
Human Ether-a-go-go-Related Gene inhibition	-	0.8653	86.53%
Micronuclear	+	0.8759	87.59%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.7700	77.00%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.9575	95.75%
Acute Oral Toxicity (c)	IV	0.4155	41.55%
Estrogen receptor binding	-	0.6373	63.73%
Androgen receptor binding	+	0.7848	78.48%
Thyroid receptor binding	-	0.7377	73.77%
Glucocorticoid receptor binding	+	0.6738	67.38%
Aromatase binding	-	0.8620	86.20%
PPAR gamma	+	0.6178	61.78%
Honey bee toxicity	-	0.9185	91.85%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9224	92.24%

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	99.69%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.49%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.30%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.16%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.48%	95.56%
CHEMBL217	P14416	Dopamine D2 receptor	87.89%	95.62%
CHEMBL2581	P07339	Cathepsin D	86.40%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.88%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.28%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.97%	90.71%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.08%	85.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.81%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.49%	86.33%

Plants that contains it

• Actiniopteris radiata
• Agave utahensis
• Aglaia elaeagnoidea
• Aglaia laxiflora
• Aristolochia littoralis
• Artemisia bigelovii
• Artemisia carvifolia
• Astragalus gummifer
• Blainvillea dichotoma
• Callicarpa maingayi
• Cardiospermum halicacabum
• Centaurea cadmea
• Centaurea nigrescens
• Cephalaria uralensis
• Cirsium japonicum
• Coreopsis fasciculata
• Crepis foetida
• Crinum viviparum
• Crotalaria aegyptiaca
• Cuphea carthagenensis
• Cyathocline purpurea
• Dicoma capensis
• Digitalis isabelliana
• Dioscoreophyllum cumminsii
• Dorstenia lindeniana
• Ericameria parryi
• Erigeron canadensis
• Euphorbia humifusa
• Euphorbia maculata
• Euphorbia segetalis
• Euphorbia turczaninowii
• Garcinia celebica
• Geranium sylvaticum
• Glycyrrhiza squamulosa
• Haplophyllum ferganicum
• Mallotus repandus
• Mnium hornum
• Morus cathayana
• Ozoroa insignis
• Parastrephia lepidophylla
• Pelargonium reniforme
• Penstemon secundiflorus
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Phyllanthus flexuosus
• Phyllanthus niruri
• Phytolacca acinosa
• Piper arboreum
• Plantago alpina
• Pouzolzia occidentalis
• Pulicaria wightiana
• Punica granatum
• Ruta microcarpa
• Scopolia carniolica
• Selinum carvifolium
• Senecio scandens
• Sidastrum multiflorum
• Sonchus ortunoi
• Styrax ferrugineus
• Syncolostemon parviflorus
• Tanacetum parthenium
• Thermopsis lanceolata
• Thuja plicata
• Triglochin maritima
• Urtica triangularis
• Valeriana hardwickii
• Vincetoxicum hirundinaria
• Yucca gloriosa var. tristis
• Zanthoxylum schreberi

Cross-Links

• PubChem: 102004656
• NPASS: NPC171715
• LOTUS: LTS0271703
• wikiData: Q105126715