Alizarin

Details

• Internal ID: e6e2a46b-33d1-4642-9c2e-466ce2d25543
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 1,2-dihydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)O)O
• InChI: InChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H
• InChI Key: RGCKGOZRHPZPFP-UHFFFAOYSA-N
• Popularity: 10,568 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₈O₄
• Molecular Weight: 240.21 g/mol
• Exact Mass: 240.04225873 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 72-48-0
• 1,2-dihydroxyanthracene-9,10-dione
• Alizarin Red
• Mordant Red 11
• 1,2-Dihydroxyanthraquinone
• Alizarin B
• Turkey Red
• 1,2-Dihydroxy-9,10-anthracenedione
• ALIZARINE
• 1,2-Anthraquinonediol
• Alizarina
• Alizarine Red
• Eljon Madder
• Alizarine B
• Alizarine NAC
• Alizarine Red B
• Alizarine Red L
• Alizerine NAC
• Eljon Madder M
• 1,2-Dihydroxy-9,10-anthraquinone
• Alizarine 3B
• Alizarine L paste
• Alizarine Red IP
• Turkey Red W
• Alizarine indicator
• Alizarine Red B2
• Certiqual Alizarine
• Alizarine Red IPP
• Alizerine Red IPP
• Mitsui Alizarine B
• Sanyo Carmine L2B
• Mitsui Alizarine BS
• Certiqual Alizarine D
• 1,2-Dihydroxyanthra-9,10-quinone
• Alizarine Lake Red 2P
• Alizarine Lake Red 3P
• Alizarine Lake Red IPX
• C.I. Mordant Red 11
• C.I. Mordant Red 11C
• D And C Orange Number 15
• D and C Orange Number 15D
• Deep Crimson Madder 10821
• Deep Crimson Madder 10821E
• 1,2-Dihydroxyanthrachinon
• Anthraquinonic
• C.I. 58000
• 1,2-Dihydroxy anthraquinone
• Alizarine paste 20% bluish
• 9,10-Anthracenedione, 1,2-dihydroxy-
• Alizarine Paste 20 percent Bluish
• Alizarinprimeveroside
• C.I. 58000C
• 1,2-Dihydroxy-anthraquinone
• D and C Orange No. 15
• Turkey Red (VAN)
• CCRIS 3530
• Anthraquinone, 1,2-dihydroxy-
• CHEBI:16866
• NSC7212
• CI 58000
• NSC 7212
• EINECS 200-782-5
• UNII-60MEW57T9G
• BRN 1914037
• 60MEW57T9G
• 1322-60-7
• DTXSID5045960
• AI3-18244
• 1,2-Dihydroxyanthrachinon [Czech]
• NSC-7212
• MFCD00001201
• DIHYDROXY-9,10-ANTHRACENEDIONE
• CHEMBL55814
• DTXCID3025960
• ROUGE COVALAC W 3514
• 4-08-00-03256 (Beilstein Handbook Reference)
• 1,2-dihydroxy-9,10-dihydroanthracene-9,10-dione
• Az
• D&C ORANGE NO. 15 (DELISTED)
• NCGC00095227-01
• crimson madder
• rose madder
• alizarin crimson
• CAS-72-48-0
• Hystazarin
• Pincoffin
• 9,10-Anthracenedione, dihydroxy-
• Alizarin, p.a.
• Sanyo Carmine l2BT
• ATHRAQUINONES A
• Spectrum_000386
• SpecPlus_000320
• 9, 1,2-dihydroxy-
• ALIZARIN [MI]
• Spectrum2_000397
• Spectrum3_000262
• Spectrum4_001555
• Spectrum5_000150
• 1,2-dihydroxyanthraquinon
• Epitope ID:116187
• SCHEMBL18614
• BSPBio_001704
• CBDivE_014227
• KBioGR_002050
• KBioSS_000866
• SPECTRUM210850
• 1, 2- dihydroxyanthraquinone
• MLS002207283
• DivK1c_006416
• Alizarin, Dye content 97 %
• SPBio_000613
• KBio1_001360
• KBio2_000866
• KBio2_003434
• KBio2_006002
• KBio3_001204
• CI 58000 [INCI]
• HMS1923C03
• HMS3651P05
• 1,10-dihydroxy-2,9-anthraquinone
• 2,9-dihydroxy-1,10-anthraquinone
• 9,10-dihydroxy-1,2-anthraquinone
• HY-N0563
• Tox21_111486
• BBL027327
• BDBM50206434
• CCG-38668
• s2526
• STK801841
• AKOS001639988
• Tox21_111486_1
• ?1,2-Dihydroxy-9,10-anthracenedione
• 1,2-Dihydroxyanthra-9,10-quinone #
• FS-3935
• LN: L C666 BV IVJ EQ FQ1
• SDCCGMLS-0066502.P001
• NCGC00095227-02
• NCGC00095227-03
• NCGC00095227-04
• NCGC00095227-06
• 1,2-bis(oxidanyl)anthracene-9,10-dione
• AC-11708
• LS-20667
• NCI60_041501
• SMR001306798
• SY012985
• 1, 2- dihydroxyanthraquinone (CI 58000)
• CS-0009103
• D0242
• FT-0621965
• SW101224-2
• C01474
• EN300-136088
• F17721
• A837539
• AE-641/00185064
• Q267813
• SR-05000002485
• SR-05000002485-1
• W-104489
• BRD-K73191876-001-04-7
• F0905-1727
• InChI=1/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9746	97.46%
Caco-2	-	0.7462	74.62%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7846	78.46%
OATP2B1 inhibitior	-	0.7174	71.74%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9659	96.59%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9118	91.18%
P-glycoprotein inhibitior	-	0.9530	95.30%
P-glycoprotein substrate	-	0.9657	96.57%
CYP3A4 substrate	-	0.6574	65.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8234	82.34%
CYP3A4 inhibition	-	0.9015	90.15%
CYP2C9 inhibition	+	0.6130	61.30%
CYP2C19 inhibition	-	0.8994	89.94%
CYP2D6 inhibition	-	0.8724	87.24%
CYP1A2 inhibition	+	0.8636	86.36%
CYP2C8 inhibition	-	0.9467	94.67%
CYP inhibitory promiscuity	-	0.8609	86.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8675	86.75%
Carcinogenicity (trinary)	Warning	0.5731	57.31%
Eye corrosion	-	0.9895	98.95%
Eye irritation	+	0.9836	98.36%
Skin irritation	+	0.7820	78.20%
Skin corrosion	-	0.9068	90.68%
Ames mutagenesis	+	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9081	90.81%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	+	0.4909	49.09%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6595	65.95%
Acute Oral Toxicity (c)	III	0.5724	57.24%
Estrogen receptor binding	+	0.8736	87.36%
Androgen receptor binding	+	0.7369	73.69%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.9241	92.41%
Aromatase binding	+	0.7777	77.77%
PPAR gamma	+	0.7184	71.84%
Honey bee toxicity	-	0.8612	86.12%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9862	98.62%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	35481.3 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM; 18869.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	1150 nM	Ki	PMID: 23167494
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	15848.9 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	5011.9 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	15848.9 nM	Potency	via CMAUP
CHEMBL4878	Q16678	Cytochrome P450 1B1	500 nM	Ki	via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 39810.7 nM; 31622.8 nM; 39810.7 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	15848.9 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	1620 nM	Ki	PMID: 23167494
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	15848.9 nM; 31622.8 nM; 10000 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM; 8912.5 nM; 12589.3 nM; 15848.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	22387.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.92%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.33%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.35%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.98%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.93%	99.15%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	87.03%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.27%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.18%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.13%	82.69%
CHEMBL2535	P11166	Glucose transporter	82.89%	98.75%

Plants that contains it

• Alangium platanifolium
• Cinchona calisaya
• Cinchona pubescens
• Croton penduliflorus
• Galium album subsp. prusense
• Galium odoratum
• Galium rubioides
• Gynochthodes umbellata
• Lychnophora salicifolia
• Morinda citrifolia
• Neolitsea konishii
• Oldenlandia umbellata
• Populus tomentosa
• Reynoutria japonica
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rubia alata
• Rubia argyi
• Rubia cordifolia
• Rubia peregrina
• Rubia tinctorum
• Senna obtusifolia
• Vepris louisii
• Vitex negundo

Cross-Links

• PubChem: 6293
• NPASS: NPC294226
• ChEMBL: CHEMBL55814
• LOTUS: LTS0078250
• wikiData: Q267813