(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Details

• Internal ID: bc63d980-c937-4279-bf1e-3225c688a33b
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 2-benzopyrans
• IUPAC Name: (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• SMILES (Canonical): C1=C(C=C(C2=C1C(=O)OC3C2OC(C(C3O)O)CO)O)O
• SMILES (Isomeric): C1=C(C=C(C2=C1C(=O)O[C@H]3[C@H]2O[C@@H]([C@H]([C@@H]3O)O)CO)O)O
• InChI: InChI=1S/C13H14O8/c14-3-7-9(17)10(18)12-11(20-7)8-5(13(19)21-12)1-4(15)2-6(8)16/h1-2,7,9-12,14-18H,3H2/t7-,9-,10+,11+,12-/m1/s1
• InChI Key: ASMJEFOVGPJHRZ-AZOIZPIDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄O₈
• Molecular Weight: 298.24 g/mol
• Exact Mass: 298.06886740 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.21
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5179	51.79%
Caco-2	-	0.9353	93.53%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5142	51.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3593	35.93%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9755	97.55%
P-glycoprotein inhibitior	-	0.9399	93.99%
P-glycoprotein substrate	-	0.9528	95.28%
CYP3A4 substrate	-	0.5223	52.23%
CYP2C9 substrate	-	0.8022	80.22%
CYP2D6 substrate	-	0.8348	83.48%
CYP3A4 inhibition	-	0.9315	93.15%
CYP2C9 inhibition	-	0.9530	95.30%
CYP2C19 inhibition	-	0.9428	94.28%
CYP2D6 inhibition	-	0.9468	94.68%
CYP1A2 inhibition	-	0.9273	92.73%
CYP2C8 inhibition	-	0.8817	88.17%
CYP inhibitory promiscuity	-	0.9206	92.06%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7220	72.20%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.5544	55.44%
Skin irritation	-	0.7643	76.43%
Skin corrosion	-	0.9643	96.43%
Ames mutagenesis	+	0.5912	59.12%
Human Ether-a-go-go-Related Gene inhibition	-	0.5320	53.20%
Micronuclear	+	0.5392	53.92%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8160	81.60%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5730	57.30%
Acute Oral Toxicity (c)	IV	0.4084	40.84%
Estrogen receptor binding	-	0.6417	64.17%
Androgen receptor binding	-	0.4828	48.28%
Thyroid receptor binding	-	0.5207	52.07%
Glucocorticoid receptor binding	-	0.5656	56.56%
Aromatase binding	-	0.7101	71.01%
PPAR gamma	+	0.5641	56.41%
Honey bee toxicity	-	0.8069	80.69%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.4184	41.84%

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	98.50%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.72%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.25%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.74%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.86%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.20%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.43%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.96%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.18%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.40%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.25%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10063249
• LOTUS: LTS0026683
• wikiData: Q104917935