(3R,4S,5R,6R)-3,4,5,6,7-pentahydroxy-1-(4-hydroxyphenyl)heptane-1,2-dione

Details

• Internal ID: 69359228-88ed-4875-83fd-ba0efd45086f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Heptoses
• IUPAC Name: (3R,4S,5R,6R)-3,4,5,6,7-pentahydroxy-1-(4-hydroxyphenyl)heptane-1,2-dione
• SMILES (Canonical): C1=CC(=CC=C1C(=O)C(=O)C(C(C(C(CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C(=O)C(=O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O
• InChI: InChI=1S/C13H16O8/c14-5-8(16)10(18)12(20)13(21)11(19)9(17)6-1-3-7(15)4-2-6/h1-4,8,10,12-16,18,20-21H,5H2/t8-,10-,12+,13+/m1/s1
• InChI Key: KOUKJYNKOCFWNE-JBYGLJPXSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₈
• Molecular Weight: 300.26 g/mol
• Exact Mass: 300.08451746 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.42
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• AKOS025287824
• (3R,4S,5R,6R)-3,4,5,6,7-pentahydroxy-1-(4-hydroxyphenyl)heptane-1,2-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7549	75.49%
Caco-2	-	0.8721	87.21%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6412	64.12%
OATP2B1 inhibitior	-	0.7138	71.38%
OATP1B1 inhibitior	+	0.8660	86.60%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9699	96.99%
P-glycoprotein inhibitior	-	0.9692	96.92%
P-glycoprotein substrate	-	0.8542	85.42%
CYP3A4 substrate	-	0.6285	62.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7850	78.50%
CYP3A4 inhibition	-	0.7998	79.98%
CYP2C9 inhibition	-	0.9559	95.59%
CYP2C19 inhibition	-	0.9584	95.84%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.8824	88.24%
CYP2C8 inhibition	-	0.6655	66.55%
CYP inhibitory promiscuity	-	0.9785	97.85%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8532	85.32%
Carcinogenicity (trinary)	Non-required	0.7450	74.50%
Eye corrosion	-	0.9918	99.18%
Eye irritation	+	0.5242	52.42%
Skin irritation	-	0.6534	65.34%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8101	81.01%
Micronuclear	-	0.6385	63.85%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.6233	62.33%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5973	59.73%
Acute Oral Toxicity (c)	III	0.6717	67.17%
Estrogen receptor binding	-	0.4837	48.37%
Androgen receptor binding	+	0.5566	55.66%
Thyroid receptor binding	-	0.5122	51.22%
Glucocorticoid receptor binding	+	0.6520	65.20%
Aromatase binding	-	0.5132	51.32%
PPAR gamma	-	0.5788	57.88%
Honey bee toxicity	-	0.9700	97.00%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	-	0.5811	58.11%

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	88.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.14%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.73%	99.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	85.94%	100.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.29%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.25%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.49%	95.56%

Plants that contains it

• Thymus vulgaris

Cross-Links

• PubChem: 67958976
• LOTUS: LTS0186103
• wikiData: Q105143996