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

Details

• Internal ID: 197f6556-609c-4f3a-8b05-30556863a0db
• Taxonomy: Benzenoids > Anthracenes > Anthracenecarboxylic acids and derivatives > Anthracenecarboxylic acids
• IUPAC Name: 9-[(9R)-2-carboxy-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-[(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(C2C5C6=C(C(=CC=C6)OC7C(C(C(C(O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=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]2C5C6=C(C(=CC=C6)OC7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=O)O)C=C(C=C4O)C(=O)O
• InChI: InChI=1S/C42H38O20/c43-11-23-31(47)35(51)37(53)41(61-23)59-21-5-1-3-15-25(17-7-13(39(55)56)9-19(45)27(17)33(49)29(15)21)26-16-4-2-6-22(60-42-38(54)36(52)32(48)24(12-44)62-42)30(16)34(50)28-18(26)8-14(40(57)58)10-20(28)46/h1-10,23-26,31-32,35-38,41-48,51-54H,11-12H2,(H,55,56)(H,57,58)/t23-,24-,25-,26?,31-,32-,35+,36+,37-,38-,41-,42?/m1/s1
• InChI Key: IPQVTOJGNYVQEO-WTEAEMSWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₃₈O₂₀
• Molecular Weight: 862.70 g/mol
• Exact Mass: 862.19564360 g/mol
• Topological Polar Surface Area (TPSA): 348.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): -1.10
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 9

Synonyms

• AKOS025402188
• AC-6076

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6788	67.88%
Caco-2	-	0.9030	90.30%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5329	53.29%
OATP2B1 inhibitior	-	0.7034	70.34%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9724	97.24%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7575	75.75%
P-glycoprotein inhibitior	+	0.6686	66.86%
P-glycoprotein substrate	-	0.8533	85.33%
CYP3A4 substrate	+	0.5805	58.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8793	87.93%
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	+	0.6697	66.97%
CYP inhibitory promiscuity	-	0.8607	86.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6966	69.66%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8881	88.81%
Skin irritation	-	0.8466	84.66%
Skin corrosion	-	0.9636	96.36%
Ames mutagenesis	+	0.5731	57.31%
Human Ether-a-go-go-Related Gene inhibition	+	0.7755	77.55%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.9177	91.77%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5571	55.71%
Acute Oral Toxicity (c)	IV	0.5235	52.35%
Estrogen receptor binding	+	0.8197	81.97%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7203	72.03%
Honey bee toxicity	-	0.8382	83.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8150	81.50%
Fish aquatic toxicity	+	0.8498	84.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	707.9 nM	Potency	via Super-PRED
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	158.5 nM; 158.5 nM; 112.2 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	316.2 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	125.9 nM; 100 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	97.27%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.89%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.55%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.40%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.29%	86.33%
CHEMBL3194	P02766	Transthyretin	89.11%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.90%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.47%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.45%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.07%	96.09%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.29%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.53%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.90%	96.21%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.15%	89.67%

Plants that contains it

• Rheum officinale
• Rheum palmatum
• Senna alexandrina

Cross-Links

• PubChem: 53486254
• NPASS: NPC173856