(2R,4aR,6R,7S,8S,8aR)-2-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxine-7,8-diol

Details

• Internal ID: 8679698d-4ad0-4fe7-ac45-de66d62d9f7d
• Taxonomy: Organoheterocyclic compounds > Pyranodioxins
• IUPAC Name: (2R,4aR,6R,7S,8S,8aR)-2-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxine-7,8-diol
• SMILES (Canonical): C1C(OC2C(C(C(OC2O1)CO)O)O)C3=CC(=C(C=C3)O)O
• SMILES (Isomeric): C1[C@H](O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O1)CO)O)O)C3=CC(=C(C=C3)O)O
• InChI: InChI=1S/C14H18O8/c15-4-9-11(18)12(19)13-14(22-9)20-5-10(21-13)6-1-2-7(16)8(17)3-6/h1-3,9-19H,4-5H2/t9-,10+,11-,12+,13-,14-/m1/s1
• InChI Key: CTVFMNLFBWRHJH-QQOHENMQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₈
• Molecular Weight: 314.29 g/mol
• Exact Mass: 314.10016753 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.01
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6101	61.01%
Caco-2	-	0.8105	81.05%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5103	51.03%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	+	0.8804	88.04%
OATP1B3 inhibitior	+	0.9668	96.68%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9653	96.53%
P-glycoprotein inhibitior	-	0.9259	92.59%
P-glycoprotein substrate	-	0.9056	90.56%
CYP3A4 substrate	-	0.5461	54.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7778	77.78%
CYP3A4 inhibition	-	0.9648	96.48%
CYP2C9 inhibition	-	0.9241	92.41%
CYP2C19 inhibition	-	0.8927	89.27%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.9392	93.92%
CYP2C8 inhibition	-	0.7540	75.40%
CYP inhibitory promiscuity	-	0.8247	82.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6401	64.01%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8954	89.54%
Skin irritation	-	0.8105	81.05%
Skin corrosion	-	0.9616	96.16%
Ames mutagenesis	+	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6071	60.71%
Micronuclear	+	0.5218	52.18%
Hepatotoxicity	-	0.7050	70.50%
skin sensitisation	-	0.8817	88.17%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8384	83.84%
Acute Oral Toxicity (c)	IV	0.4800	48.00%
Estrogen receptor binding	-	0.6789	67.89%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5974	59.74%
Glucocorticoid receptor binding	-	0.5478	54.78%
Aromatase binding	-	0.6085	60.85%
PPAR gamma	+	0.5779	57.79%
Honey bee toxicity	-	0.8248	82.48%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.4763	47.63%

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	99.60%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.66%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	93.62%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.62%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.18%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	87.30%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.28%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.69%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.66%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.48%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.34%	99.15%
CHEMBL3438	Q05513	Protein kinase C zeta	81.99%	88.48%

Plants that contains it

• Sargentodoxa cuneata

Cross-Links

• PubChem: 11688229
• NPASS: NPC220110
• LOTUS: LTS0174428
• wikiData: Q104970083