Emodin anthrone

Details

• Internal ID: 5bd65a0b-faf7-4270-8481-6d94e7861ea9
• Taxonomy: Benzenoids > Anthracenes
• IUPAC Name: 1,3,8-trihydroxy-6-methyl-10H-anthracen-9-one
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2)C=C(C=C3O)O
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2)C=C(C=C3O)O
• InChI: InChI=1S/C15H12O4/c1-7-2-8-4-9-5-10(16)6-12(18)14(9)15(19)13(8)11(17)3-7/h2-3,5-6,16-18H,4H2,1H3
• InChI Key: LAJSXCAVRQXZIO-UHFFFAOYSA-N
• Popularity: 92 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25 g/mol
• Exact Mass: 256.07355886 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• Emodinanthrone
• 491-60-1
• 1,3,8-Trihydroxy-6-methyl-10H-anthracen-9-one
• 1,3,8-Trihydroxy-6-methylanthrone
• emodin-9-anthrone
• Emodinol
• Frangula emodin anthrone
• CHEMBL122192
• UNII-77C500W1A2
• 9(10H)-Anthracenone, 1,3,8-trihydroxy-6-methyl-
• 77C500W1A2
• 1,6,8-trihydroxy-3-methyl-10-hydroanthracen-9-one
• Emodinanthranol
• Emodin anthranol
• Protophyscihydrone
• 2,4,5-trihydroxy-7-methylanthracen-10(9H)-one
• Frangulaemodinanthrone
• Frangulaemodinanthranol
• D00BSX
• SCHEMBL6046328
• DTXSID80197684
• CHEBI:150013
• LAJSXCAVRQXZIO-UHFFFAOYSA-N
• BCP29231
• HY-N9362
• BDBM50060878
• AKOS025401350
• AC-1208
• CS-0159524
• ANTHRONE, 1,3,8-TRIHYDROXY-6-METHYL-
• 1,3,8,9-TETRAHYDROXY-6-METHYLANTHRACENE
• 1,3,8-Trihydroxy-6-methyl-9(10H)-Anthracenone
• 1,3,8-trihydroxy-6-methylanthracen-9(10H)-one
• Q27266578
• 1,3,8-TRIHYDROXY-6-METHYL-9,10-DIHYDROANTHRACEN-9-ONE
• Emodinanthrone pound>>1,3,8-Trihydroxy-6-methyl-10H-anthracen-9-one 1,6,8-Trihydroxy-3-methyl-10-hydroanthracen-9-one 9(10H)-Anthracenone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9821	98.21%
Caco-2	+	0.8593	85.93%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7581	75.81%
OATP2B1 inhibitior	-	0.5660	56.60%
OATP1B1 inhibitior	+	0.9406	94.06%
OATP1B3 inhibitior	+	0.9642	96.42%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8543	85.43%
P-glycoprotein inhibitior	-	0.9290	92.90%
P-glycoprotein substrate	-	0.9821	98.21%
CYP3A4 substrate	-	0.5811	58.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7959	79.59%
CYP3A4 inhibition	+	0.7608	76.08%
CYP2C9 inhibition	+	0.7999	79.99%
CYP2C19 inhibition	+	0.6473	64.73%
CYP2D6 inhibition	-	0.7065	70.65%
CYP1A2 inhibition	+	0.9592	95.92%
CYP2C8 inhibition	-	0.9139	91.39%
CYP inhibitory promiscuity	+	0.7063	70.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8311	83.11%
Carcinogenicity (trinary)	Non-required	0.5847	58.47%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.8473	84.73%
Skin irritation	+	0.6414	64.14%
Skin corrosion	-	0.8781	87.81%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6305	63.05%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	+	0.8625	86.25%
skin sensitisation	-	0.7289	72.89%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4759	47.59%
Acute Oral Toxicity (c)	III	0.7613	76.13%
Estrogen receptor binding	+	0.7916	79.16%
Androgen receptor binding	+	0.6421	64.21%
Thyroid receptor binding	-	0.5964	59.64%
Glucocorticoid receptor binding	+	0.8943	89.43%
Aromatase binding	-	0.5794	57.94%
PPAR gamma	+	0.7049	70.49%
Honey bee toxicity	-	0.9530	95.30%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9676	96.76%

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	96.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.39%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.42%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	92.29%	96.12%
CHEMBL3401	O75469	Pregnane X receptor	90.25%	94.73%
CHEMBL4208	P20618	Proteasome component C5	88.57%	90.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.85%	96.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.19%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.14%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.45%	90.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.28%	93.03%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.70%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.50%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.28%	96.09%

Plants that contains it

• Artemisia scoparia
• Baccharis sulcata
• Blechnum fluviatile
• Epimedium koreanum
• Frangula alnus
• Frangula purshiana
• Fridericia triplinervia
• Garcinia smeathmanii
• Maclura tinctoria
• Magnolia figo
• Myrsine africana
• Paeonia emodi
• Polygonum perfoliatum
• Ravenia spectabilis
• Reynoutria japonica
• Reynoutria multiflora
• Rhamnus davurica
• Rhamnus prinoides
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rumex acetosa
• Rumex crispus
• Rumex dentatus
• Rumex japonicus
• Rumex nepalensis
• Senna occidentalis
• Senna podocarpa
• Senna tora
• Stevia berlandieri

Cross-Links

• PubChem: 122635
• NPASS: NPC267205
• ChEMBL: CHEMBL122192
• LOTUS: LTS0215291
• wikiData: Q27266578