(4R,5S,8R,9S)-8-[(1S)-1,2-dihydroxyethyl]-4-(3,4-dihydroxyphenyl)-9-hydroxy-1,7-dioxaspiro[4.4]nonane-2,6-dione

Details

• Internal ID: 5c16a3f8-6fbd-492f-b48e-f341baab9adc
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: (4R,5S,8R,9S)-8-[(1S)-1,2-dihydroxyethyl]-4-(3,4-dihydroxyphenyl)-9-hydroxy-1,7-dioxaspiro[4.4]nonane-2,6-dione
• InChI: InChI=1S/C15H16O9/c16-5-10(19)12-13(21)15(14(22)23-12)7(4-11(20)24-15)6-1-2-8(17)9(18)3-6/h1-3,7,10,12-13,16-19,21H,4-5H2/t7-,10+,12-,13+,15+/m1/s1
• InChI Key: DEBXNSRAVPKCJM-KAVSNOHRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₉
• Molecular Weight: 340.28 g/mol
• Exact Mass: 340.07943208 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.49
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6447	64.47%
Caco-2	-	0.9184	91.84%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6325	63.25%
OATP2B1 inhibitior	-	0.7229	72.29%
OATP1B1 inhibitior	+	0.9298	92.98%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9153	91.53%
P-glycoprotein inhibitior	-	0.9300	93.00%
P-glycoprotein substrate	-	0.8133	81.33%
CYP3A4 substrate	+	0.5315	53.15%
CYP2C9 substrate	-	0.5940	59.40%
CYP2D6 substrate	-	0.8165	81.65%
CYP3A4 inhibition	-	0.8503	85.03%
CYP2C9 inhibition	-	0.9239	92.39%
CYP2C19 inhibition	-	0.9418	94.18%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9251	92.51%
CYP2C8 inhibition	-	0.7736	77.36%
CYP inhibitory promiscuity	-	0.9533	95.33%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6035	60.35%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8428	84.28%
Skin irritation	-	0.7374	73.74%
Skin corrosion	-	0.9212	92.12%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7104	71.04%
Micronuclear	+	0.5432	54.32%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7817	78.17%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7666	76.66%
Acute Oral Toxicity (c)	III	0.5863	58.63%
Estrogen receptor binding	+	0.7009	70.09%
Androgen receptor binding	+	0.6828	68.28%
Thyroid receptor binding	-	0.5721	57.21%
Glucocorticoid receptor binding	+	0.6351	63.51%
Aromatase binding	-	0.5522	55.22%
PPAR gamma	-	0.6136	61.36%
Honey bee toxicity	-	0.8501	85.01%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.6478	64.78%

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	98.75%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.65%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.42%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.78%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.42%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.22%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.07%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.65%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.89%	90.71%
CHEMBL4208	P20618	Proteasome component C5	84.30%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.37%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.09%	85.14%

Plants that contains it

• Leucadendron argenteum

Cross-Links

• PubChem: 162895601
• LOTUS: LTS0072142
• wikiData: Q104977073