(3E,4aS,6R,7S,8S,8aR)-7,8-dihydroxy-6-(hydroxymethyl)-3-[(4-hydroxyphenyl)methylidene]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]dioxin-2-one

Details

• Internal ID: e3cf8556-a597-4d07-a985-964967f07b07
• Taxonomy: Organoheterocyclic compounds > Pyranodioxins
• IUPAC Name: (3E,4aS,6R,7S,8S,8aR)-7,8-dihydroxy-6-(hydroxymethyl)-3-[(4-hydroxyphenyl)methylidene]-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]dioxin-2-one
• SMILES (Canonical): C1=CC(=CC=C1C=C2C(=O)OC3C(C(C(OC3O2)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/2\C(=O)O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3O2)CO)O)O)O
• InChI: InChI=1S/C15H16O8/c16-6-10-11(18)12(19)13-15(22-10)21-9(14(20)23-13)5-7-1-3-8(17)4-2-7/h1-5,10-13,15-19H,6H2/b9-5+/t10-,11-,12+,13-,15-/m1/s1
• InChI Key: SVRMKLADDRLSAP-DICFCACXSA-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): 126.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.89
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6581	65.81%
Caco-2	-	0.7736	77.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5636	56.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7175	71.75%
OATP1B3 inhibitior	+	0.9735	97.35%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8301	83.01%
P-glycoprotein inhibitior	-	0.9138	91.38%
P-glycoprotein substrate	-	0.9204	92.04%
CYP3A4 substrate	-	0.5178	51.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8454	84.54%
CYP3A4 inhibition	-	0.9190	91.90%
CYP2C9 inhibition	-	0.9367	93.67%
CYP2C19 inhibition	-	0.9057	90.57%
CYP2D6 inhibition	-	0.9135	91.35%
CYP1A2 inhibition	-	0.9113	91.13%
CYP2C8 inhibition	-	0.7376	73.76%
CYP inhibitory promiscuity	-	0.8229	82.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6688	66.88%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.6001	60.01%
Skin irritation	-	0.7549	75.49%
Skin corrosion	-	0.9617	96.17%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5866	58.66%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.7983	79.83%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5637	56.37%
Acute Oral Toxicity (c)	III	0.3327	33.27%
Estrogen receptor binding	-	0.6766	67.66%
Androgen receptor binding	+	0.5420	54.20%
Thyroid receptor binding	-	0.5924	59.24%
Glucocorticoid receptor binding	-	0.6599	65.99%
Aromatase binding	-	0.5976	59.76%
PPAR gamma	+	0.5206	52.06%
Honey bee toxicity	-	0.7890	78.90%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7775	77.75%

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	98.41%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.38%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	88.43%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	87.26%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.98%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.13%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.46%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.05%	99.17%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.97%	88.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.60%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.49%	97.09%

Plants that contains it

• Umbilicus rupestris

Cross-Links

• PubChem: 102007847
• LOTUS: LTS0186405
• wikiData: Q105262396