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

Details

• Internal ID: c9b9e613-6898-4ecc-b87f-7e8c6efac1ad
• Taxonomy: Benzenoids > Phenols > 1-hydroxy-2-unsubstituted benzenoids
• IUPAC Name: (4S,5S,8R,9S)-8-[(1S)-1,2-dihydroxyethyl]-9-hydroxy-4-(4-hydroxyphenyl)-1,7-dioxaspiro[4.4]nonane-2,6-dione
• SMILES (Canonical): C1C(C2(C(C(OC2=O)C(CO)O)O)OC1=O)C3=CC=C(C=C3)O
• SMILES (Isomeric): C1[C@H]([C@@]2([C@H]([C@H](OC2=O)[C@H](CO)O)O)OC1=O)C3=CC=C(C=C3)O
• InChI: InChI=1S/C15H16O8/c16-6-10(18)12-13(20)15(14(21)22-12)9(5-11(19)23-15)7-1-3-8(17)4-2-7/h1-4,9-10,12-13,16-18,20H,5-6H2/t9-,10-,12+,13-,15-/m0/s1
• InChI Key: JVCLQSJXGOABTC-KKQCIPQASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₈
• Molecular Weight: 324.28 g/mol
• Exact Mass: 324.08451746 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.20
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• CHEMBL1979330
• NSC106976
• NSC-106976
• NCI60_000167

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5959	59.59%
Caco-2	-	0.8748	87.48%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6424	64.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8532	85.32%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9383	93.83%
P-glycoprotein inhibitior	-	0.9021	90.21%
P-glycoprotein substrate	-	0.7478	74.78%
CYP3A4 substrate	+	0.5484	54.84%
CYP2C9 substrate	-	0.5935	59.35%
CYP2D6 substrate	-	0.8101	81.01%
CYP3A4 inhibition	-	0.8544	85.44%
CYP2C9 inhibition	-	0.9449	94.49%
CYP2C19 inhibition	-	0.9529	95.29%
CYP2D6 inhibition	-	0.9440	94.40%
CYP1A2 inhibition	-	0.9406	94.06%
CYP2C8 inhibition	-	0.7351	73.51%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5676	56.76%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9270	92.70%
Skin irritation	-	0.7348	73.48%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8503	85.03%
Micronuclear	-	0.5068	50.68%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8265	82.65%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.4891	48.91%
Acute Oral Toxicity (c)	III	0.6067	60.67%
Estrogen receptor binding	+	0.5756	57.56%
Androgen receptor binding	+	0.6523	65.23%
Thyroid receptor binding	-	0.6454	64.54%
Glucocorticoid receptor binding	+	0.5692	56.92%
Aromatase binding	-	0.7177	71.77%
PPAR gamma	-	0.5689	56.89%
Honey bee toxicity	-	0.8539	85.39%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7241	72.41%
Fish aquatic toxicity	-	0.4222	42.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	95.82%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.39%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.95%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.43%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.65%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.51%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.93%	89.00%
CHEMBL299	P17252	Protein kinase C alpha	84.82%	98.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.78%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.51%	95.89%

Plants that contains it

• Krameria erecta

Cross-Links

• PubChem: 6711168
• LOTUS: LTS0089821
• wikiData: Q105135598