(3S)-3,8,9-trihydroxy-6-methoxy-3-methyl-7-[(E)-3-methylbut-1-enyl]-2,4-dihydroanthracen-1-one

Details

• Internal ID: bb20b218-3ec2-4203-875c-250e9bf0f895
• Taxonomy: Benzenoids > Anthracenes
• IUPAC Name: (3S)-3,8,9-trihydroxy-6-methoxy-3-methyl-7-[(E)-3-methylbut-1-enyl]-2,4-dihydroanthracen-1-one
• SMILES (Canonical): CC(C)C=CC1=C(C2=C(C3=C(CC(CC3=O)(C)O)C=C2C=C1OC)O)O
• SMILES (Isomeric): CC(C)/C=C/C1=C(C2=C(C3=C(C[C@](CC3=O)(C)O)C=C2C=C1OC)O)O
• InChI: InChI=1S/C21H24O5/c1-11(2)5-6-14-16(26-4)8-12-7-13-9-21(3,25)10-15(22)17(13)20(24)18(12)19(14)23/h5-8,11,23-25H,9-10H2,1-4H3/b6-5+/t21-/m0/s1
• InChI Key: QEMNROQOCQGNHL-LYSGITKLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.16237386 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.81
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	+	0.7479	74.79%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7349	73.49%
OATP2B1 inhibitior	-	0.7182	71.82%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4750	47.50%
P-glycoprotein inhibitior	-	0.6904	69.04%
P-glycoprotein substrate	-	0.6858	68.58%
CYP3A4 substrate	+	0.5896	58.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8378	83.78%
CYP3A4 inhibition	+	0.6359	63.59%
CYP2C9 inhibition	-	0.6196	61.96%
CYP2C19 inhibition	+	0.6124	61.24%
CYP2D6 inhibition	-	0.7678	76.78%
CYP1A2 inhibition	+	0.8001	80.01%
CYP2C8 inhibition	-	0.6427	64.27%
CYP inhibitory promiscuity	-	0.5482	54.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9055	90.55%
Carcinogenicity (trinary)	Non-required	0.5791	57.91%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.6716	67.16%
Skin irritation	-	0.7539	75.39%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4813	48.13%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8100	81.00%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.4543	45.43%
Acute Oral Toxicity (c)	III	0.5219	52.19%
Estrogen receptor binding	+	0.7448	74.48%
Androgen receptor binding	+	0.5538	55.38%
Thyroid receptor binding	+	0.6707	67.07%
Glucocorticoid receptor binding	+	0.8019	80.19%
Aromatase binding	+	0.7348	73.48%
PPAR gamma	+	0.8093	80.93%
Honey bee toxicity	-	0.7734	77.34%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9930	99.30%

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	99.39%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	95.82%	94.75%
CHEMBL2581	P07339	Cathepsin D	94.44%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.03%	85.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.85%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.81%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.93%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.39%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.91%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.41%	96.09%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	86.69%	80.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.14%	94.00%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	86.13%	81.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.54%	91.03%
CHEMBL2535	P11166	Glucose transporter	85.26%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.82%	96.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.51%	94.42%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.12%	98.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.57%	91.07%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.45%	93.03%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.45%	99.15%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.12%	89.50%
CHEMBL4208	P20618	Proteasome component C5	80.36%	90.00%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	80.20%	95.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.12%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.06%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.00%	89.00%

Plants that contains it

• Vismia baccifera

Cross-Links

• PubChem: 163193514
• LOTUS: LTS0125690
• wikiData: Q105219294