Chrysophanol-9-anthrone

Details

• Internal ID: 4c0269d1-6118-4c34-8769-27a71c43ae26
• Taxonomy: Benzenoids > Anthracenes
• IUPAC Name: 1,8-dihydroxy-3-methyl-10H-anthracen-9-one
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2)C=CC=C3O
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2)C=CC=C3O
• InChI: InChI=1S/C15H12O3/c1-8-5-10-7-9-3-2-4-11(16)13(9)15(18)14(10)12(17)6-8/h2-6,16-17H,7H2,1H3
• InChI Key: ZZBWSNKBZKPGAK-UHFFFAOYSA-N
• Popularity: 30 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25 g/mol
• Exact Mass: 240.078644241 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• Chrysophanol anthrone
• Chrysothrone
• 491-58-7
• Chrysophanic acid 9-anthrone
• 1,8-Dihydroxy-3-methylanthracen-9(10H)-one
• Chrysophanic acid-9-anthrone
• Chrysophanolanthrone
• Chrysarobin (pure substance)
• CCRIS 644
• CHEBI:3686
• CHEMBL122196
• 1,8-dihydroxy-3-methylanthrone
• UNII-6307EF51M1
• 1,8-dihydroxy-3-methyl-10H-anthracen-9-one
• 1,8-dihydroxy-3-methyl-9(10H)-anthracenone
• EINECS 207-740-5
• Anthrone, 1,8-dihydroxy-3-methyl-
• 6307EF51M1
• AI3-16523
• Chrysophanolanthron
• CHRYSAROBINUM
• CHRYSAROBIN CRUDE FROM GOA POWDER
• Spectrum_001297
• SpecPlus_000166
• CHRYSAROBIN [MI]
• Spectrum2_000592
• Spectrum3_001277
• Spectrum4_001657
• Spectrum5_000533
• CHRYSAROBINUM [HPUS]
• BSPBio_002874
• CHRYSAROBIN [WHO-DD]
• KBioGR_002153
• KBioSS_001777
• DivK1c_006262
• SPBio_000464
• SCHEMBL1003557
• KBio1_001206
• KBio2_001777
• KBio2_004345
• KBio2_006913
• KBio3_002374
• DTXSID20197683
• BDBM50060892
• CCG-39165
• LMPK13040005
• NCGC00178414-01
• 1,8-DIHYDROXY-3-METHYL-9-ANTHRONE
• LS-187738
• 9(10H)-Anthracenone, 1,8-dihydroxy-3-methyl-
• SR-05000002486
• SR-05000002486-1
• Q27106164

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.9000	90.00%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8554	85.54%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9500	95.00%
OATP1B3 inhibitior	+	0.9744	97.44%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7874	78.74%
P-glycoprotein inhibitior	-	0.9406	94.06%
P-glycoprotein substrate	-	0.9550	95.50%
CYP3A4 substrate	-	0.5723	57.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7959	79.59%
CYP3A4 inhibition	-	0.7947	79.47%
CYP2C9 inhibition	+	0.7191	71.91%
CYP2C19 inhibition	+	0.5890	58.90%
CYP2D6 inhibition	-	0.8377	83.77%
CYP1A2 inhibition	+	0.9538	95.38%
CYP2C8 inhibition	-	0.9475	94.75%
CYP inhibitory promiscuity	+	0.5752	57.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7824	78.24%
Carcinogenicity (trinary)	Non-required	0.4494	44.94%
Eye corrosion	-	0.9871	98.71%
Eye irritation	+	0.5472	54.72%
Skin irritation	+	0.7215	72.15%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5901	59.01%
Micronuclear	+	0.5759	57.59%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.7090	70.90%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5899	58.99%
Acute Oral Toxicity (c)	III	0.6710	67.10%
Estrogen receptor binding	+	0.8170	81.70%
Androgen receptor binding	+	0.7066	70.66%
Thyroid receptor binding	-	0.6202	62.02%
Glucocorticoid receptor binding	+	0.9330	93.30%
Aromatase binding	+	0.5711	57.11%
PPAR gamma	+	0.7376	73.76%
Honey bee toxicity	-	0.9695	96.95%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9673	96.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.52%	95.56%
CHEMBL2581	P07339	Cathepsin D	96.68%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.88%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	93.17%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	91.50%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.61%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	90.09%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.62%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.75%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.30%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.80%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.73%	93.99%
CHEMBL2056	P21728	Dopamine D1 receptor	80.70%	91.00%

Plants that contains it

• Baccharis sulcata
• Blechnum fluviatile
• Frangula purshiana
• Fridericia triplinervia
• Garcinia smeathmanii
• Maclura tinctoria
• Magnolia figo
• Ravenia spectabilis
• Rumex acetosa
• Rumex crispus
• Stevia berlandieri

Cross-Links

• PubChem: 68111
• NPASS: NPC173978
• ChEMBL: CHEMBL122196
• LOTUS: LTS0227860
• wikiData: Q27106164