Damnacanthol

Details

• Internal ID: c4b2b104-88ce-44bc-840c-38681175a743
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 3-hydroxy-2-(hydroxymethyl)-1-methoxyanthracene-9,10-dione
• SMILES (Canonical): COC1=C2C(=CC(=C1CO)O)C(=O)C3=CC=CC=C3C2=O
• SMILES (Isomeric): COC1=C2C(=CC(=C1CO)O)C(=O)C3=CC=CC=C3C2=O
• InChI: InChI=1S/C16H12O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-6,17-18H,7H2,1H3
• InChI Key: ASFZQCLAQPBWDN-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26 g/mol
• Exact Mass: 284.06847348 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 477-83-8
• Damnacantol
• 3-hydroxy-2-(hydroxymethyl)-1-methoxyanthracene-9,10-dione
• CCRIS 6439
• UNII-8YF10MN2ZW
• 8YF10MN2ZW
• CHEMBL522932
• MEGxp0_001331
• SCHEMBL16225889
• ACon1_000070
• DTXSID50197252
• NCGC00168823-01
• LS-188133
• E87123
• BRD-K68527930-001-01-9
• Q27271209
• 3-hydroxy-2-(hydroxymethyl)-1-methoxy-anthracene-9,10-dione
• 9,10-Anthracenedione, 3-hydroxy-2-(hydroxymethyl)-1-methoxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9774	97.74%
Caco-2	-	0.6766	67.66%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7714	77.14%
OATP2B1 inhibitior	-	0.7205	72.05%
OATP1B1 inhibitior	+	0.8546	85.46%
OATP1B3 inhibitior	+	0.9189	91.89%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7325	73.25%
P-glycoprotein inhibitior	-	0.8489	84.89%
P-glycoprotein substrate	-	0.9121	91.21%
CYP3A4 substrate	-	0.5472	54.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7239	72.39%
CYP3A4 inhibition	-	0.8015	80.15%
CYP2C9 inhibition	-	0.6027	60.27%
CYP2C19 inhibition	-	0.6108	61.08%
CYP2D6 inhibition	-	0.9215	92.15%
CYP1A2 inhibition	+	0.7939	79.39%
CYP2C8 inhibition	-	0.7957	79.57%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8553	85.53%
Carcinogenicity (trinary)	Non-required	0.7057	70.57%
Eye corrosion	-	0.9888	98.88%
Eye irritation	+	0.8416	84.16%
Skin irritation	-	0.7537	75.37%
Skin corrosion	-	0.9446	94.46%
Ames mutagenesis	+	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7597	75.97%
Micronuclear	+	0.5559	55.59%
Hepatotoxicity	-	0.6307	63.07%
skin sensitisation	-	0.8336	83.36%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6881	68.81%
Acute Oral Toxicity (c)	III	0.6664	66.64%
Estrogen receptor binding	+	0.8917	89.17%
Androgen receptor binding	+	0.5641	56.41%
Thyroid receptor binding	-	0.5738	57.38%
Glucocorticoid receptor binding	+	0.8627	86.27%
Aromatase binding	+	0.6805	68.05%
PPAR gamma	+	0.7958	79.58%
Honey bee toxicity	-	0.9116	91.16%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9497	94.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.44%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.98%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.62%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	90.75%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.55%	86.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.35%	82.69%
CHEMBL2535	P11166	Glucose transporter	88.27%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.03%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.37%	96.09%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.85%	96.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.51%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.50%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	82.88%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.49%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.21%	94.73%
CHEMBL1907	P15144	Aminopeptidase N	81.17%	93.31%
CHEMBL4208	P20618	Proteasome component C5	81.16%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.78%	94.00%

Plants that contains it

• Damnacanthus indicus
• Damnacanthus major
• Faramea occidentalis
• Heterophyllaea pustulata
• Hymenodictyon orixense
• Knoxia roxburghii
• Lasianthus acuminatissimus
• Morinda angustifolia
• Morinda citrifolia
• Morinda lucida
• Neonauclea calycina

Cross-Links

• PubChem: 160474
• NPASS: NPC290954
• LOTUS: LTS0215557
• wikiData: Q27271209