(2R,3S,4S,4aR,10bS)-3,4,7,8,9-pentahydroxy-2-(hydroxymethyl)-10-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Details

• Internal ID: 1c9bdbbe-94bb-4b5c-bc8d-dccc0ae5310c
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives
• IUPAC Name: (2R,3S,4S,4aR,10bS)-3,4,7,8,9-pentahydroxy-2-(hydroxymethyl)-10-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• SMILES (Canonical): COC1=C(C(=C(C2=C1C3C(C(C(C(O3)CO)O)O)OC2=O)O)O)O
• SMILES (Isomeric): COC1=C(C(=C(C2=C1[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC2=O)O)O)O
• InChI: InChI=1S/C14H16O10/c1-22-11-5-4(7(17)8(18)10(11)20)14(21)24-13-9(19)6(16)3(2-15)23-12(5)13/h3,6,9,12-13,15-20H,2H2,1H3/t3-,6-,9+,12+,13-/m1/s1
• InChI Key: RLMBUCMLLDGPLX-OBVHKQFISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₁₀
• Molecular Weight: 344.27 g/mol
• Exact Mass: 344.07434670 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.50
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5405	54.05%
Caco-2	-	0.9099	90.99%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5367	53.67%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	-	0.4149	41.49%
OATP1B3 inhibitior	+	0.9762	97.62%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9298	92.98%
P-glycoprotein inhibitior	-	0.8289	82.89%
P-glycoprotein substrate	-	0.9204	92.04%
CYP3A4 substrate	+	0.5338	53.38%
CYP2C9 substrate	-	0.7968	79.68%
CYP2D6 substrate	-	0.8383	83.83%
CYP3A4 inhibition	-	0.9107	91.07%
CYP2C9 inhibition	-	0.9346	93.46%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.8772	87.72%
CYP2C8 inhibition	-	0.8632	86.32%
CYP inhibitory promiscuity	-	0.8094	80.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6881	68.81%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.7168	71.68%
Skin irritation	-	0.7987	79.87%
Skin corrosion	-	0.9617	96.17%
Ames mutagenesis	-	0.5354	53.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5607	56.07%
Micronuclear	+	0.5333	53.33%
Hepatotoxicity	-	0.6571	65.71%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6094	60.94%
Acute Oral Toxicity (c)	III	0.7058	70.58%
Estrogen receptor binding	+	0.7206	72.06%
Androgen receptor binding	-	0.5438	54.38%
Thyroid receptor binding	-	0.5164	51.64%
Glucocorticoid receptor binding	+	0.6506	65.06%
Aromatase binding	-	0.6917	69.17%
PPAR gamma	-	0.5532	55.32%
Honey bee toxicity	-	0.8113	81.13%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.5385	53.85%

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	98.67%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.57%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.38%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.77%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.17%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.82%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	85.96%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.25%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.25%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.43%	89.00%

Plants that contains it

• Tridax procumbens

Cross-Links

• PubChem: 101160774
• LOTUS: LTS0089308
• wikiData: Q105240243