Negletein

Details

• Internal ID: 5793ee65-3cd5-42c4-9b1d-bacc2b479499
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5,6-dihydroxy-7-methoxy-2-phenylchromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=CC=C3)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=CC=C3)O)O
• InChI: InChI=1S/C16H12O5/c1-20-13-8-12-14(16(19)15(13)18)10(17)7-11(21-12)9-5-3-2-4-6-9/h2-8,18-19H,1H3
• InChI Key: ZTHLHHDJRXJGRX-UHFFFAOYSA-N
• Popularity: 30 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26 g/mol
• Exact Mass: 284.06847348 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 29550-13-8
• 5,6-Dihydroxy-7-methoxyflavone
• Baicalein-7-methylether
• 5,6-Dihydroxy-7-methoxy-2-phenyl-4H-chromen-4-one
• 7-O-Methylbaicalein
• 4H-1-Benzopyran-4-one, 5,6-dihydroxy-7-methoxy-2-phenyl-
• 5,6-dihydroxy-7-methoxy-2-phenylchromen-4-one
• CHEMBL296800
• ST055981
• 5,6-Dihydroxy-7-methoxy-2-phenyl-chromen-4-one
• SCHEMBL718970
• 5,6-dihydroxy-7-methoxy-2-phenyl-1-benzopyran-4-one
• DTXSID50183736
• CHEBI:190121
• ZTHLHHDJRXJGRX-UHFFFAOYSA-N
• BCP33551
• HY-N4285
• BDBM50212750
• LMPK12111097
• MFCD00017458
• AKOS024282370
• MS-24037
• CS-0032637
• FT-0619824
• E80605
• A819959
• 5,6-Dihydroxy-7-methoxyflavone;7-O-Methylbaicalein
• 7-methoxy-5,6-bis(oxidanyl)-2-phenyl-chromen-4-one
• NCGC00385058-01!5,6-dihydroxy-7-methoxy-2-phenylchromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9577	95.77%
Caco-2	-	0.6328	63.28%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7944	79.44%
OATP2B1 inhibitior	-	0.5780	57.80%
OATP1B1 inhibitior	+	0.9102	91.02%
OATP1B3 inhibitior	+	0.9965	99.65%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6663	66.63%
P-glycoprotein inhibitior	+	0.7635	76.35%
P-glycoprotein substrate	-	0.8416	84.16%
CYP3A4 substrate	-	0.5103	51.03%
CYP2C9 substrate	-	0.6887	68.87%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.7179	71.79%
CYP2C9 inhibition	+	0.5494	54.94%
CYP2C19 inhibition	+	0.6827	68.27%
CYP2D6 inhibition	-	0.9018	90.18%
CYP1A2 inhibition	+	0.9263	92.63%
CYP2C8 inhibition	+	0.7117	71.17%
CYP inhibitory promiscuity	+	0.6056	60.56%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5596	55.96%
Eye corrosion	-	0.9766	97.66%
Eye irritation	+	0.8303	83.03%
Skin irritation	-	0.5899	58.99%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6364	63.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.7376	73.76%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9318	93.18%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8158	81.58%
Acute Oral Toxicity (c)	III	0.6733	67.33%
Estrogen receptor binding	+	0.8999	89.99%
Androgen receptor binding	+	0.8809	88.09%
Thyroid receptor binding	+	0.5442	54.42%
Glucocorticoid receptor binding	+	0.8664	86.64%
Aromatase binding	+	0.8840	88.40%
PPAR gamma	+	0.8043	80.43%
Honey bee toxicity	-	0.7919	79.19%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5151	51.51%
Fish aquatic toxicity	+	0.8838	88.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.41%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.80%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.86%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.64%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.79%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.68%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.59%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.38%	89.00%
CHEMBL1255126	O15151	Protein Mdm4	83.47%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.14%	99.17%

Plants that contains it

• Centaurea clementei
• Colebrookea oppositifolia
• Desmos cochinchinensis
• Desmos dumosus
• Elsholtzia ciliata
• Mosla chinensis
• Ononis angustissima
• Stachys palustris

Cross-Links

• PubChem: 471719
• NPASS: NPC275722
• ChEMBL: CHEMBL296800
• LOTUS: LTS0007594
• wikiData: Q83054550