Aurin

Details

• Internal ID: c15d2616-7581-449e-a1eb-3227c423e84e
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Diphenylmethanes
• IUPAC Name: 4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
• SMILES (Canonical): C1=CC(=O)C=CC1=C(C2=CC=C(C=C2)O)C3=CC=C(C=C3)O
• SMILES (Isomeric): C1=CC(=O)C=CC1=C(C2=CC=C(C=C2)O)C3=CC=C(C=C3)O
• InChI: InChI=1S/C19H14O3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20-21H
• InChI Key: FYEHYMARPSSOBO-UHFFFAOYSA-N
• Popularity: 471 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₄O₃
• Molecular Weight: 290.30 g/mol
• Exact Mass: 290.094294304 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.59
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 603-45-2
• Corallin
• Aurine
• 4,4'-Dihydroxyfuchsone
• Aurin No. 555
• C.I. 43800
• 2,5-Cyclohexadien-1-one, 4-[bis(4-hydroxyphenyl)methylene]-
• 85N4AK3JAU
• 4-[bis(4-hydroxyphenyl)methylene]cyclohexa-2,5-dien-1-one
• DTXSID2022387
• NSC-7805
• 4-(Bis(4-hydroxyphenyl)methylene)cyclohexa-2,5-dien-1-one
• 2,5-Cyclohexadien-1-one, 4-(bis(4-hydroxyphenyl)methylene)-
• 4-(Bis(p-hydroxyphenyl)methylene)cyclohexa-2,5-dien-1-one
• RefChem:115651
• DTXCID002387
• 4(bis(p-hydroxyphenyl)methylene)-2,5-cyclohexadien-1-one
• 210-041-8
• rosolic acid
• p-Rosolic acid
• 4-(Bis(4-hydroxyphenyl)methylene)cyclohexa-2,5-dienone
• Pararosolic Acid
• 4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
• MFCD00001624
• NSC 7805
• NSC7805
• 4-[Bis(4-hydroxyphenyl)methylene]-2,5-cyclohexadienone
• CI-43800
• 2,5-Cyclohexadien-1-one, 4-(bis(p-hydroxyphenyl)methylene)-
• SMR001224399
• UNII-85N4AK3JAU
• EINECS 210-041-8
• Spectrum_000988
• 4-[Bis(4-hydroxyphenyl)methylene]-2,5-cyclohexadien-1-one
• AI3-18245
• Spectrum2_000762
• Spectrum3_000609
• Spectrum4_000904
• Spectrum5_001864
• AURIN [MI]
• Corallin yellow (Salt/Mix)
• p-Rosolic acid, 85.0%
• BSPBio_002118
• KBioGR_001368
• KBioSS_001468
• MLS001359834
• MLS002695900
• BIDD:ER0176
• DivK1c_000400
• SCHEMBL590856
• SPECTRUM1500762
• SPBio_000804
• CHEMBL210868
• orb1744532
• CHEBI:34544
• HMS501D22
• KBio1_000400
• KBio2_001468
• KBio2_004036
• KBio2_006604
• KBio3_001618
• NINDS_000400
• HMS1923K11
• HMS3058N04
• p-Rosolic acid, JIS special grade
• p-Rosolic acid (C.I. 43800)
• p-Rosolic acid, Dye content 85 %
• BDBM50427512
• CCG-39006
• SBB058277
• STL453788
• AKOS015903417
• FA01472
• HY-W104821
• 2, 4-[bis(p-hydroxyphenyl)methylene]-
• IDI1_000400
• SMP1_000134
• 2, 4-[bis(4-hydroxyphenyl)methylene]-
• NCGC00095266-01
• NCGC00095266-02
• NCGC00095266-03
• DA-61323
• NCI60_041721
• ST080685
• SY045767
• A0598
• CS-0157463
• NS00034335
• D88291
• F448730
• Q423995
• BRD-K24453427-001-02-9
• BRD-K24453427-001-04-5
• 2,5-Cyclohexadien-1-one, 4-[bis(p-hydroxyphenyl)]methylene-
• 4-[Bis(4-hydroxyphenyl)methylene]-2,5-cyclohexadien-1-one #
• 4-(P,P'-DIHYDROXYBENZHYDRYLIDENE)-2,5-CYCLOHEXADIEN-1-ONE
• p-Rosolic acid;4-[Bis(4-hydroxyphenyl)methylene]-2,5-cyclohexadienone;Corallin

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.6044	60.44%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8590	85.90%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9085	90.85%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6395	63.95%
P-glycoprotein inhibitior	-	0.9297	92.97%
P-glycoprotein substrate	-	0.9456	94.56%
CYP3A4 substrate	-	0.6459	64.59%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8075	80.75%
CYP3A4 inhibition	-	0.5157	51.57%
CYP2C9 inhibition	-	0.5335	53.35%
CYP2C19 inhibition	+	0.6313	63.13%
CYP2D6 inhibition	-	0.9271	92.71%
CYP1A2 inhibition	+	0.6404	64.04%
CYP2C8 inhibition	+	0.4447	44.47%
CYP inhibitory promiscuity	+	0.8199	81.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.5527	55.27%
Carcinogenicity (trinary)	Non-required	0.5155	51.55%
Eye corrosion	-	0.9811	98.11%
Eye irritation	+	0.9822	98.22%
Skin irritation	-	0.5269	52.69%
Skin corrosion	-	0.9843	98.43%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8885	88.85%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.6264	62.64%
skin sensitisation	+	0.8845	88.45%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	+	0.6186	61.86%
Acute Oral Toxicity (c)	III	0.4759	47.59%
Estrogen receptor binding	+	0.8786	87.86%
Androgen receptor binding	+	0.7997	79.97%
Thyroid receptor binding	+	0.5418	54.18%
Glucocorticoid receptor binding	+	0.9090	90.90%
Aromatase binding	+	0.8855	88.55%
PPAR gamma	+	0.7753	77.53%
Honey bee toxicity	-	0.9645	96.45%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9869	98.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	31622.8 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	25118.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL1741165	O75030	Microphthalmia-associated transcription factor	9916 nM; 9916 nM; 9916 nM	AC50; AC50; AC50	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	4466.8 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	3548.1 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	50000 nM	EC50	PMID: 23414143
CHEMBL2362980	Q06710	Paired box protein Pax-8	8810 nM	AC50	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3548.1 nM	Potency	via CMAUP
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	2630.27 nM	IC50	PMID: 23571415
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	4073.8 nM	IC50	PMID: 23571415
CHEMBL1293232	Q16637	Survival motor neuron protein	35481.3 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.49%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	87.70%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.78%	95.56%
CHEMBL4208	P20618	Proteasome component C5	86.00%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.21%	86.33%
CHEMBL3194	P02766	Transthyretin	83.25%	90.71%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.74%	85.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5100
• NPASS: NPC135784
• ChEMBL: CHEMBL210868