Anthragallol

Details

• Internal ID: 346ff8db-671b-45b5-8316-28f8e08115d9
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 1,2,3-trihydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=CC(=C(C(=C3C2=O)O)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=CC(=C(C(=C3C2=O)O)O)O
• InChI: InChI=1S/C14H8O5/c15-9-5-8-10(14(19)13(9)18)12(17)7-4-2-1-3-6(7)11(8)16/h1-5,15,18-19H
• InChI Key: AHKDJQYHVWSRLT-UHFFFAOYSA-N
• Popularity: 128 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₈O₅
• Molecular Weight: 256.21 g/mol
• Exact Mass: 256.03717335 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 602-64-2
• Anthracene brown
• Anthragallic acid
• 1,2,3-Trihydroxyanthraquinone
• Antragallol
• Alizarine Brown HD
• Alizarine Brown R
• Anthracene Brown G
• Anthracene Brown N
• Anthracene Brown S
• Antracromo Brown D
• Anthracene Brown FD
• Anthracene Brown FF
• Anthracene Brown WH
• Anthracene Brown WL
• C.I. Mordant Brown 42
• Chrome Fast Brown FC
• Mitsui Anthracene Brown
• Anthracene Printing Brown
• 1,2,3-trihydroxyanthracene-9,10-dione
• 1,2,3-Trihydroxy-9,10-anthracenedione
• C.I. 58200
• CCRIS 5595
• ANTHRAQUINONE, 1,2,3-TRIHYDROXY-
• 9,10-Anthracenedione, 1,2,3-trihydroxy-
• NSC31754
• EINECS 210-022-4
• NSC 31754
• BRN 2058042
• AI3-00802
• CHEBI:2755
• CHEMBL192032
• UNII-845J3299E1
• NSC-31754
• 1,2,3-trihydroxy-9,10-anthraquinone
• 845J3299E1
• 4-08-00-03567 (Beilstein Handbook Reference)
• ACID BROWN
• Alizarin Brown R
• boc-cys(bzl)-ol
• ANTHRAGALLOL [MI]
• 1,3-Trihydroxyanthraquinone
• 9, 1,2,3-trihydroxy-
• SCHEMBL555230
• Anthraquinone,2,3-trihydroxy-
• 1,2,3-Trihydroxy-Anthraquinone
• DTXSID80208946
• AHKDJQYHVWSRLT-UHFFFAOYSA-N
• BDBM50400184
• 1,3-Trihydroxy-9,10-anthracenedione
• 1,3,10-trihydroxy-2,9-anthraquinone
• 1,9,10-trihydroxy-2,3-anthraquinone
• 2,3,9-trihydroxy-1,10-anthraquinone
• 3,4,10-trihydroxy-2,9-anthraquinone
• 3,9,10-trihydroxy-1,2-anthraquinone
• ANTHRACENE BROWN, WATER SOLUBLE
• 1,2,3-Trihydroxyanthra-9,10-quinone
• LS-20714
• PD119402
• C.I.58200
• FT-0662242
• Q5413057
• 1,2,3-trihydroxy-9,10-dihydroanthracene-9,10-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9440	94.40%
Caco-2	-	0.6984	69.84%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6168	61.68%
OATP2B1 inhibitior	-	0.6949	69.49%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9137	91.37%
P-glycoprotein inhibitior	-	0.9496	94.96%
P-glycoprotein substrate	-	0.9834	98.34%
CYP3A4 substrate	-	0.6549	65.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8234	82.34%
CYP3A4 inhibition	-	0.7561	75.61%
CYP2C9 inhibition	-	0.5531	55.31%
CYP2C19 inhibition	-	0.9382	93.82%
CYP2D6 inhibition	-	0.8606	86.06%
CYP1A2 inhibition	+	0.7851	78.51%
CYP2C8 inhibition	-	0.8927	89.27%
CYP inhibitory promiscuity	-	0.7853	78.53%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8875	88.75%
Carcinogenicity (trinary)	Non-required	0.4953	49.53%
Eye corrosion	-	0.9927	99.27%
Eye irritation	+	0.9879	98.79%
Skin irritation	+	0.7486	74.86%
Skin corrosion	-	0.8518	85.18%
Ames mutagenesis	+	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8731	87.31%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	+	0.5730	57.30%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4623	46.23%
Acute Oral Toxicity (c)	III	0.6165	61.65%
Estrogen receptor binding	+	0.8030	80.30%
Androgen receptor binding	+	0.7214	72.14%
Thyroid receptor binding	-	0.4940	49.40%
Glucocorticoid receptor binding	+	0.9138	91.38%
Aromatase binding	+	0.6800	68.00%
PPAR gamma	+	0.7934	79.34%
Honey bee toxicity	-	0.9208	92.08%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9820	98.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	1325 nM; 583 nM	Ki; Ki	PMID: 24095762; PMID: 23167494
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	1211 nM; 270 nM	Ki; Ki	PMID: 24095762; PMID: 23167494

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.80%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.80%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.94%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.47%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.45%	99.15%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.25%	82.69%
CHEMBL2535	P11166	Glucose transporter	87.18%	98.75%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.48%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.73%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.59%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.40%	90.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.18%	93.03%

Plants that contains it

• Coprosma lucida
• Croton steenkampianus
• Daphne aurantiaca
• Garcinia cantleyana
• Hymenodictyon orixense
• Lonicera korolkowii
• Philotheca brucei
• Portulaca pilosa
• Pteridium aquilinum
• Rubia tinctorum

Cross-Links

• PubChem: 11768
• NPASS: NPC203063
• ChEMBL: CHEMBL192032
• LOTUS: LTS0247322
• wikiData: Q5413057