3-(hydroxymethyl)-2,4,4-trimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexa-2,5-dien-1-one

Details

• Internal ID: 77bebff3-ced6-40b4-a53e-6fb476c7feba
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: 3-(hydroxymethyl)-2,4,4-trimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexa-2,5-dien-1-one
• SMILES (Canonical): CC1=C(C(C=C(C1=O)OC2C(C(C(C(O2)CO)O)O)O)(C)C)CO
• SMILES (Isomeric): CC1=C(C(C=C(C1=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)(C)C)CO
• InChI: InChI=1S/C16H24O8/c1-7-8(5-17)16(2,3)4-9(11(7)19)23-15-14(22)13(21)12(20)10(6-18)24-15/h4,10,12-15,17-18,20-22H,5-6H2,1-3H3/t10-,12-,13+,14-,15-/m1/s1
• InChI Key: YQTJCDJCMPVAJX-TVKJYDDYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₈
• Molecular Weight: 344.36 g/mol
• Exact Mass: 344.14711772 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.40
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5226	52.26%
Caco-2	-	0.7985	79.85%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8633	86.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8927	89.27%
OATP1B3 inhibitior	+	0.9142	91.42%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6577	65.77%
P-glycoprotein inhibitior	-	0.8894	88.94%
P-glycoprotein substrate	-	0.9313	93.13%
CYP3A4 substrate	+	0.5589	55.89%
CYP2C9 substrate	-	0.8043	80.43%
CYP2D6 substrate	-	0.8732	87.32%
CYP3A4 inhibition	-	0.9814	98.14%
CYP2C9 inhibition	-	0.8326	83.26%
CYP2C19 inhibition	-	0.8391	83.91%
CYP2D6 inhibition	-	0.9132	91.32%
CYP1A2 inhibition	-	0.8476	84.76%
CYP2C8 inhibition	-	0.8865	88.65%
CYP inhibitory promiscuity	-	0.7813	78.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7032	70.32%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9579	95.79%
Skin irritation	-	0.7972	79.72%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	+	0.5330	53.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.5545	55.45%
Micronuclear	-	0.7941	79.41%
Hepatotoxicity	-	0.7763	77.63%
skin sensitisation	-	0.8007	80.07%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6934	69.34%
Acute Oral Toxicity (c)	III	0.6090	60.90%
Estrogen receptor binding	+	0.5461	54.61%
Androgen receptor binding	-	0.5638	56.38%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5372	53.72%
Aromatase binding	+	0.5400	54.00%
PPAR gamma	+	0.6323	63.23%
Honey bee toxicity	-	0.8008	80.08%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.7800	78.00%

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	95.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.56%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.54%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.92%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.84%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.78%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.45%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.30%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.45%	96.00%

Plants that contains it

• Crocus sativus

Cross-Links

• PubChem: 100914023
• LOTUS: LTS0182364
• wikiData: Q105352570