Purpurin

Details

• Internal ID: 16826047-1cb8-4e98-aa05-ef0d772c2bb6
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 1,2,4-trihydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3O)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3O)O)O
• InChI: InChI=1S/C14H8O5/c15-8-5-9(16)14(19)11-10(8)12(17)6-3-1-2-4-7(6)13(11)18/h1-5,15-16,19H
• InChI Key: BBNQQADTFFCFGB-UHFFFAOYSA-N
• Popularity: 803 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: 2.90
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 81-54-9
• Verantin
• 1,2,4-Trihydroxyanthraquinone
• Hydroxylizaric acid
• Purpurine
• 1,2,4-trihydroxyanthracene-9,10-dione
• Smoke Brown G
• 1,2,4-Trihydroxy-9,10-anthracenedione
• 1,2,4-Trihydroxy-9,10-anthraquinone
• 1,2,4-Trihydroxyanthrachinon
• C.I. 58205
• Anthraquinone, 1,2,4-trihydroxy-
• 9,10-Anthracenedione, 1,2,4-trihydroxy-
• C.I. 75410
• CCRIS 3527
• CHEBI:8645
• 1,2,4-Trihydroxyanthra-9,10-quinone
• Alizarin purpurin
• C.I. Natural Red 16
• C.I. 1037
• UNII-L1GT81LS6N
• EINECS 201-359-8
• L1GT81LS6N
• NSC 10447
• BRN 1887127
• DTXSID4021214
• C.I. Natural Red 8
• PURPURIN (DYE)
• NSC-10447
• 1,2,4-Trihydroxyanthrachinon [Czech]
• MLS002473304
• DTXCID401214
• 1,2,4-Trihydroxy-Anthraquinone
• 4-08-00-03568 (Beilstein Handbook Reference)
• NSC10447
• SMR001306802
• 1,2,4-trihydroxy-9,10-dihydroanthracene-9,10-dione
• Madder purple
• Oxylizarinic acid
• 4-Hydroxyalizarin
• C14H8O5
• 9TF
• MFCD00001203
• Purpurin (85per cent)
• PURPURIN [MI]
• Spectrum2_000037
• Spectrum3_001947
• 1,4-Trihydroxyanthrachinon
• D0XJ7I
• Epitope ID:116185
• NCIMech_000036
• 1,4-Trihydroxyanthraquinone
• cid_6683
• 9, 1,2,4-trihydroxy-
• SCHEMBL33871
• BSPBio_003547
• 1,2,4-trihydroxyanthraquinon
• hsp90_173
• MLS002207287
• SPECTRUM1505300
• Purpurin, Dye content 90 %
• SPBio_000133
• Anthraquinone,2,4-trihydroxy-
• CHEMBL294264
• BDBM67454
• KBio3_002835
• HMS2232F04
• HMS3374D11
• HY-N0571
• Tox21_301526
• 1,4-Trihydroxy-9,10-anthraquinone
• CCG-35463
• s4963
• STK396669
• AKOS001482720
• 1,2,4-Trihydroxy-9,10-anthrachinon
• 4,9,10-trihydroxy-1,2-anthraquinone
• SDCCGMLS-0066870.P001
• CAS-81-54-9
• NCGC00095346-01
• NCGC00095346-02
• NCGC00095346-03
• NCGC00255399-01
• WLN: L C666 BV IVJ DQ EQ GQ
• AC-34603
• AS-63166
• LS-20715
• NCI60_000107
• 1,2,4-Trihydroxyanthra-9,10-quinone #
• 1,2,4-tris(oxidanyl)anthracene-9,10-dione
• CS-0009108
• EU-0000318
• FT-0699020
• P0605
• Purpurin, for spectrophotometric det. (of B, Pb)
• Q116472
• SR-05000002508
• SR-05000002508-1
• InChI=1/C14H8O5/c15-8-5-9(16)14(19)11-10(8)12(17)6-3-1-2-4-7(6)13(11)18/h1-5,15-16,19

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9440	94.40%
Caco-2	-	0.7297	72.97%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6168	61.68%
OATP2B1 inhibitior	-	0.6989	69.89%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8835	88.35%
P-glycoprotein inhibitior	-	0.9352	93.52%
P-glycoprotein substrate	-	0.9760	97.60%
CYP3A4 substrate	-	0.6778	67.78%
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	-	0.9285	92.85%
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	+	0.9845	98.45%
Skin irritation	+	0.7486	74.86%
Skin corrosion	-	0.8518	85.18%
Ames mutagenesis	+	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8667	86.67%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	+	0.5730	57.30%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5307	53.07%
Acute Oral Toxicity (c)	III	0.6165	61.65%
Estrogen receptor binding	+	0.7995	79.95%
Androgen receptor binding	+	0.7405	74.05%
Thyroid receptor binding	-	0.5428	54.28%
Glucocorticoid receptor binding	+	0.9421	94.21%
Aromatase binding	+	0.7497	74.97%
PPAR gamma	+	0.8343	83.43%
Honey bee toxicity	-	0.9012	90.12%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9820	98.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM; 7079.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	3548.1 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	5011.9 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	3981.1 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5990	P38398	Breast cancer type 1 susceptibility protein	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4878	Q16678	Cytochrome P450 1B1	700 nM	Ki	via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 25118.9 nM; 39810.7 nM; 25118.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	7943.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	31622.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	15848.9 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	12589.3 nM; 19952.6 nM; 31622.8 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL3869	P50281	Matrix metalloproteinase 14	30600 nM	IC50	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	22387.2 nM; 28183.8 nM; 5011.9 nM; 5011.9 nM; 14125.4 nM; 12589.3 nM	Potency; Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1951	P21397	Monoamine oxidase A	422 nM	Ki	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	316.2 nM; 316.2 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.78%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.92%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.94%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.01%	99.15%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.28%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.86%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	85.04%	94.73%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.34%	96.67%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.66%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.36%	99.23%
CHEMBL2535	P11166	Glucose transporter	80.62%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.46%	86.33%

Plants that contains it

• Alangium platanifolium
• Cinchona calisaya
• Cinchona pubescens
• Croton penduliflorus
• Galium album subsp. prusense
• Galium mollugo
• Galium odoratum
• Galium rubioides
• Lychnophora salicifolia
• Neolitsea konishii
• Populus tomentosa
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rubia argyi
• Rubia cordifolia
• Rubia manjith
• Rubia tinctorum
• Rubia wallichiana
• Senna obtusifolia
• Tephrosia purpurea
• Vepris louisii

Cross-Links

• PubChem: 6683
• NPASS: NPC238629
• ChEMBL: CHEMBL294264
• LOTUS: LTS0111755
• wikiData: Q116472