Emodic acid

Details

• Internal ID: 21eca013-2560-4173-bec9-ee3fb322c933
• Taxonomy: Benzenoids > Anthracenes > Anthracenecarboxylic acids and derivatives > Anthracenecarboxylic acids
• IUPAC Name: 4,5,7-trihydroxy-9,10-dioxoanthracene-2-carboxylic acid
• SMILES (Canonical): C1=C(C=C(C2=C1C(=O)C3=C(C2=O)C(=CC(=C3)O)O)O)C(=O)O
• SMILES (Isomeric): C1=C(C=C(C2=C1C(=O)C3=C(C2=O)C(=CC(=C3)O)O)O)C(=O)O
• InChI: InChI=1S/C15H8O7/c16-6-3-8-12(10(18)4-6)14(20)11-7(13(8)19)1-5(15(21)22)2-9(11)17/h1-4,16-18H,(H,21,22)
• InChI Key: ZJXVNNSMRGTDBI-UHFFFAOYSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₈O₇
• Molecular Weight: 300.22 g/mol
• Exact Mass: 300.02700259 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.28
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• MLS000876948
• NSC624610
• 4,5,7-trihydroxy-9,10-dioxoanthracene-2-carboxylic acid
• SMR000440655
• 2-Anthracenecarboxylicacid, 9,10-dihydro-4,5,7-trihydroxy-9,10-dioxo-
• 4,5,7-trihydroxy-9,10-dioxo-2-anthracenecarboxylic acid
• Spectrum_000189
• SpecPlus_000784
• Spectrum2_000421
• Spectrum3_001129
• Spectrum4_001974
• Spectrum5_000645
• 4,5,7-Trihydroxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid
• BSPBio_002597
• KBioGR_002473
• KBioSS_000669
• DivK1c_006880
• SPECTRUM1504060
• SPBio_000402
• CHEMBL290914
• cid_361510
• MEGxm0_000113
• SCHEMBL5073407
• ACon0_001437
• ACon1_000410
• CHEBI:93655
• KBio1_001824
• KBio2_000669
• KBio2_003237
• KBio2_005805
• KBio3_002097
• ZJXVNNSMRGTDBI-UHFFFAOYSA-N
• BDBM115127
• HMS2267O14
• CCG-38681
• AKOS040734875
• NSC-624610
• SDCCGMLS-0066762.P001
• NCGC00095847-01
• NCGC00095847-02
• NCGC00095847-03
• 4,5,7- trihydroxy-2-carboxyanthraquinone
• HY-134000
• CS-0136365
• 4,5,7-trihydroxyanthraquinone-2-carboxylic acid
• BRD-K94841585-001-03-6
• Q27165344
• 4,5,7-trihydroxy-9,10-diketo-anthracene-2-carboxylic acid
• 4,5,7-trihydroxy-9,10-dioxo-anthracene-2-carboxylic acid
• 4,5,7-Trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• 4,5,7-tris(oxidanyl)-9,10-bis(oxidanylidene)anthracene-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9702	97.02%
Caco-2	+	0.5357	53.57%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7631	76.31%
OATP2B1 inhibitior	-	0.6784	67.84%
OATP1B1 inhibitior	+	0.9461	94.61%
OATP1B3 inhibitior	+	0.8614	86.14%
MATE1 inhibitior	-	0.5800	58.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9279	92.79%
P-glycoprotein inhibitior	-	0.9695	96.95%
P-glycoprotein substrate	-	0.9748	97.48%
CYP3A4 substrate	-	0.6594	65.94%
CYP2C9 substrate	-	0.8352	83.52%
CYP2D6 substrate	-	0.8880	88.80%
CYP3A4 inhibition	-	0.7893	78.93%
CYP2C9 inhibition	-	0.5087	50.87%
CYP2C19 inhibition	-	0.8751	87.51%
CYP2D6 inhibition	-	0.8537	85.37%
CYP1A2 inhibition	-	0.7128	71.28%
CYP2C8 inhibition	-	0.7563	75.63%
CYP inhibitory promiscuity	-	0.8676	86.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8323	83.23%
Carcinogenicity (trinary)	Non-required	0.6289	62.89%
Eye corrosion	-	0.9944	99.44%
Eye irritation	+	0.9883	98.83%
Skin irritation	+	0.6795	67.95%
Skin corrosion	-	0.9742	97.42%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8543	85.43%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.9107	91.07%
skin sensitisation	-	0.7595	75.95%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	-	0.7000	70.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7844	78.44%
Acute Oral Toxicity (c)	III	0.5798	57.98%
Estrogen receptor binding	+	0.6050	60.50%
Androgen receptor binding	+	0.6725	67.25%
Thyroid receptor binding	-	0.7252	72.52%
Glucocorticoid receptor binding	+	0.6808	68.08%
Aromatase binding	-	0.7184	71.84%
PPAR gamma	+	0.6513	65.13%
Honey bee toxicity	-	0.9307	93.07%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	35481.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	7943.3 nM	Potency	via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	14125.4 nM	Potency	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	2511.9 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	22387.2 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	7079.5 nM; 3981.1 nM; 12589.3 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	17782.8 nM; 17782.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	10000 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.73%	99.23%
CHEMBL3194	P02766	Transthyretin	92.14%	90.71%
CHEMBL2581	P07339	Cathepsin D	91.47%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.18%	95.56%
CHEMBL1811	P34995	Prostanoid EP1 receptor	91.09%	95.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.48%	91.11%
CHEMBL4208	P20618	Proteasome component C5	88.97%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.56%	89.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.24%	94.42%
CHEMBL1929	P47989	Xanthine dehydrogenase	88.15%	96.12%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.40%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	85.48%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.28%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.09%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.34%	96.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.11%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.03%	99.15%

Plants that contains it

• Andrographis neesiana
• Coreopsis tinctoria
• Magnolia ovata

Cross-Links

• PubChem: 361510
• NPASS: NPC290550
• ChEMBL: CHEMBL290914
• LOTUS: LTS0140301
• wikiData: Q27165344