Digiferruginol

Details

• Internal ID: e21c0c57-1fd0-40c0-b671-165dfdd4db21
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)CO)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)CO)O
• InChI: InChI=1S/C15H10O4/c16-7-8-5-6-11-12(13(8)17)15(19)10-4-2-1-3-9(10)14(11)18/h1-6,16-17H,7H2
• InChI Key: JCZCSQSSSAHDCB-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24 g/mol
• Exact Mass: 254.05790880 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.66
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 24094-45-9
• Deoxylucidin
• Digiferrugineol
• 1-Hydroxy-2-hydroxymethylanthraquinone
• 1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione
• BRN 2218948
• ANTHRAQUINONE, 1-HYDROXY-2-HYDROXYMETHYL-
• 1-Hydroxy-2-(hydroxymethyl)-9,10-anthracenedione
• 9,10-Anthracenedione, 1-hydroxy-2-(hydroxymethyl)-
• CHEBI:4544
• 4-08-00-03278 (Beilstein Handbook Reference)
• CHEMBL495276
• SCHEMBL23199057
• DTXSID40178818
• JCZCSQSSSAHDCB-UHFFFAOYSA-N
• AKOS040735238
• 1-hydroxy-2-(hydroxymethyl)anthraquinone
• LS-20690
• 1-Hydroxy-2-(hydroxymethyl)anthra-9,10-quinone #
• Q27106407
• 1-HYDROXY-2-(HYDROXYMETHYL)-9,10-DIHYDROANTHRACENE-9,10-DIONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9764	97.64%
Caco-2	-	0.7384	73.84%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7419	74.19%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.8971	89.71%
OATP1B3 inhibitior	+	0.8486	84.86%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8039	80.39%
P-glycoprotein inhibitior	-	0.9492	94.92%
P-glycoprotein substrate	-	0.9376	93.76%
CYP3A4 substrate	-	0.5747	57.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8175	81.75%
CYP3A4 inhibition	-	0.8474	84.74%
CYP2C9 inhibition	-	0.6783	67.83%
CYP2C19 inhibition	-	0.6161	61.61%
CYP2D6 inhibition	-	0.9034	90.34%
CYP1A2 inhibition	+	0.6838	68.38%
CYP2C8 inhibition	-	0.8891	88.91%
CYP inhibitory promiscuity	-	0.6516	65.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8485	84.85%
Carcinogenicity (trinary)	Non-required	0.7041	70.41%
Eye corrosion	-	0.9924	99.24%
Eye irritation	+	0.9472	94.72%
Skin irritation	-	0.5713	57.13%
Skin corrosion	-	0.9650	96.50%
Ames mutagenesis	+	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9233	92.33%
Micronuclear	+	0.5959	59.59%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.6969	69.69%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5136	51.36%
Acute Oral Toxicity (c)	III	0.5421	54.21%
Estrogen receptor binding	+	0.8760	87.60%
Androgen receptor binding	+	0.6906	69.06%
Thyroid receptor binding	-	0.6073	60.73%
Glucocorticoid receptor binding	+	0.8752	87.52%
Aromatase binding	+	0.8298	82.98%
PPAR gamma	+	0.8668	86.68%
Honey bee toxicity	-	0.8505	85.05%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9686	96.86%

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	98.73%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.63%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.24%	95.56%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	87.72%	96.67%
CHEMBL1951	P21397	Monoamine oxidase A	86.53%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.05%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	83.57%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.09%	91.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.20%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.87%	99.23%

Plants that contains it

• Cinchona calisaya
• Cinchona pubescens
• Digitalis ferruginea
• Galium verum
• Gynochthodes officinalis
• Gynochthodes parvifolia
• Knoxia roxburghii
• Persicaria bistorta
• Phyllanthus emblica
• Plocama pendula
• Rubia alata
• Rubia cordifolia
• Rubia wallichiana
• Streptocarpus dunnii

Cross-Links

• PubChem: 32209
• NPASS: NPC31799
• LOTUS: LTS0136793
• wikiData: Q27106407