Norartocarpetin

Details

• Internal ID: 104290f0-3da5-4ac0-b1ce-bfe36cab02ec
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 2-(2,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1O)O)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1O)O)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
• InChI: InChI=1S/C15H10O6/c16-7-1-2-9(10(18)3-7)13-6-12(20)15-11(19)4-8(17)5-14(15)21-13/h1-6,16-19H
• InChI Key: ZSYPIPFQOQGYHH-UHFFFAOYSA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.24 g/mol
• Exact Mass: 286.04773803 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 520-30-9
• 2-(2,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• L2Y5RSY4BM
• CHEMBL463145
• 4H-1-Benzopyran-4-one, 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-
• 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
• 2-(2,4-Dihydroxy-phenyl)-5,7-dihydroxy-1-benzopyran-4-one
• 2-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
• Norartocarpetin, 5
• UNII-L2Y5RSY4BM
• SCHEMBL1546435
• 5,7,2',4'-tetrahydroxyflavone
• DTXSID00199963
• 2',4',5,7-Tetrahydroxyflavone
• CHEBI:174716
• BDBM50269559
• HY-N10503
• LMPK12110941
• AKOS015906501
• MS-24075
• CS-0608332
• 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one
• Q15425765
• 2-(2,4-BIS(OXIDANYL)PHENYL)-5,7-BIS(OXIDANYL)CHROMEN-4-ONE
• 2-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9677	96.77%
Caco-2	+	0.6749	67.49%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7606	76.06%
OATP2B1 inhibitior	-	0.6083	60.83%
OATP1B1 inhibitior	+	0.8278	82.78%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7977	79.77%
P-glycoprotein inhibitior	-	0.8727	87.27%
P-glycoprotein substrate	-	0.7890	78.90%
CYP3A4 substrate	-	0.5401	54.01%
CYP2C9 substrate	-	0.6443	64.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8881	88.81%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	+	0.9254	92.54%
CYP2C8 inhibition	+	0.4627	46.27%
CYP inhibitory promiscuity	+	0.8009	80.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7003	70.03%
Eye corrosion	-	0.9917	99.17%
Eye irritation	+	0.9703	97.03%
Skin irritation	+	0.6236	62.36%
Skin corrosion	-	0.9718	97.18%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8964	89.64%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8396	83.96%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6381	63.81%
Acute Oral Toxicity (c)	II	0.5830	58.30%
Estrogen receptor binding	+	0.9114	91.14%
Androgen receptor binding	+	0.8794	87.94%
Thyroid receptor binding	+	0.6609	66.09%
Glucocorticoid receptor binding	+	0.9410	94.10%
Aromatase binding	+	0.8648	86.48%
PPAR gamma	+	0.9081	90.81%
Honey bee toxicity	-	0.8614	86.14%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9214	92.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL221	P23219	Cyclooxygenase-1	14000 nM	IC50	PMID: 11858749
CHEMBL1973	P14679	Tyrosinase	23 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.38%	91.11%
CHEMBL3194	P02766	Transthyretin	96.54%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	95.06%	98.35%
CHEMBL1951	P21397	Monoamine oxidase A	94.88%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.86%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.66%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.50%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.15%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.05%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	83.35%	94.73%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.84%	96.12%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.58%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.30%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.57%	93.40%
CHEMBL4530	P00488	Coagulation factor XIII	80.21%	96.00%
CHEMBL4208	P20618	Proteasome component C5	80.14%	90.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.05%	90.93%

Plants that contains it

• Artocarpus gomezianus
• Artocarpus heterophyllus
• Artocarpus lacucha
• Artocarpus tonkinensis
• Canthium berberidifolium
• Dalbergia sissoo
• Ficus formosana
• Maclura tricuspidata
• Morus alba
• Morus indica
• Morus nigra
• Sophora flavescens

Cross-Links

• PubChem: 5481970
• NPASS: NPC274121
• ChEMBL: CHEMBL463145
• LOTUS: LTS0089058
• wikiData: Q15425765