(9R)-4-hydroxy-10-oxo-9-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid

Details

• Internal ID: d142dfc8-93ce-4edd-a1db-f532d12e9eb3
• Taxonomy: Benzenoids > Anthracenes > Anthracenecarboxylic acids and derivatives > Anthracenecarboxylic acids
• IUPAC Name: (9R)-4-hydroxy-10-oxo-9-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid
• SMILES (Canonical): C1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4=C(C2C5C(C(C(C(O5)CO)O)O)O)C=C(C=C4O)C(=O)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)C4=C([C@@H]2C5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C=C(C=C4O)C(=O)O
• InChI: InChI=1S/C27H30O15/c28-6-13-18(31)21(34)23(36)25(40-13)15-9-2-1-3-12(41-27-24(37)22(35)19(32)14(7-29)42-27)17(9)20(33)16-10(15)4-8(26(38)39)5-11(16)30/h1-5,13-15,18-19,21-25,27-32,34-37H,6-7H2,(H,38,39)/t13-,14-,15-,18-,19-,21+,22+,23-,24-,25?,27-/m1/s1
• InChI Key: GLHYGFIHRKNBBP-QXIZLWMTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 264.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -3.21
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6788	67.88%
Caco-2	-	0.9219	92.19%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5329	53.29%
OATP2B1 inhibitior	-	0.7018	70.18%
OATP1B1 inhibitior	+	0.8884	88.84%
OATP1B3 inhibitior	+	0.9724	97.24%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6307	63.07%
P-glycoprotein inhibitior	-	0.5927	59.27%
P-glycoprotein substrate	-	0.7937	79.37%
CYP3A4 substrate	+	0.6102	61.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8781	87.81%
CYP3A4 inhibition	-	0.9365	93.65%
CYP2C9 inhibition	-	0.9171	91.71%
CYP2C19 inhibition	-	0.9032	90.32%
CYP2D6 inhibition	-	0.9596	95.96%
CYP1A2 inhibition	-	0.9320	93.20%
CYP2C8 inhibition	+	0.6637	66.37%
CYP inhibitory promiscuity	-	0.8607	86.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6966	69.66%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8927	89.27%
Skin irritation	-	0.8466	84.66%
Skin corrosion	-	0.9636	96.36%
Ames mutagenesis	+	0.6213	62.13%
Human Ether-a-go-go-Related Gene inhibition	+	0.7445	74.45%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	+	0.6691	66.91%
skin sensitisation	-	0.9177	91.77%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5384	53.84%
Acute Oral Toxicity (c)	IV	0.5235	52.35%
Estrogen receptor binding	+	0.6881	68.81%
Androgen receptor binding	-	0.5407	54.07%
Thyroid receptor binding	-	0.5631	56.31%
Glucocorticoid receptor binding	-	0.6467	64.67%
Aromatase binding	-	0.5296	52.96%
PPAR gamma	+	0.6565	65.65%
Honey bee toxicity	-	0.8292	82.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8250	82.50%
Fish aquatic toxicity	+	0.8498	84.98%

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	98.84%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.16%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	93.20%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.47%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.33%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.09%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	90.13%	83.82%
CHEMBL3194	P02766	Transthyretin	89.63%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.40%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.36%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.19%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	83.54%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.40%	89.67%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.19%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.94%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.07%	96.00%

Plants that contains it

• Rheum officinale
• Rheum palmatum
• Rheum tanguticum

Cross-Links

• PubChem: 11972450
• NPASS: NPC57465
• LOTUS: LTS0272384
• wikiData: Q105107006