Skullcapflavone I

Details

• Internal ID: f8a2488b-eb65-46a8-9214-41ff03976046
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-2-(2-hydroxyphenyl)-7,8-dimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C(=C1)O)C(=O)C=C(O2)C3=CC=CC=C3O)OC
• SMILES (Isomeric): COC1=C(C2=C(C(=C1)O)C(=O)C=C(O2)C3=CC=CC=C3O)OC
• InChI: InChI=1S/C17H14O6/c1-21-14-8-12(20)15-11(19)7-13(23-17(15)16(14)22-2)9-5-3-4-6-10(9)18/h3-8,18,20H,1-2H3
• InChI Key: CZRGNFVQUYWGKP-UHFFFAOYSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.29 g/mol
• Exact Mass: 314.07903816 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 41060-16-6
• Panicolin
• 5,2'-Dihydroxy-7,8-dimethoxyflavone
• 5-hydroxy-2-(2-hydroxyphenyl)-7,8-dimethoxychromen-4-one
• 2',5-Dihydroxy-7,8-dimethoxyflavone
• UNII-8P86A8Q1G0
• 8P86A8Q1G0
• 4H-1-Benzopyran-4-one, 5-hydroxy-2-(2-hydroxyphenyl)-7,8-dimethoxy-
• SKULLCAPFLAVONEI
• SCHEMBL6069761
• LMPK12111304
• AKOS032961992
• Skullcapflavone I, analytical standard
• Q27270850
• 55084-09-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9730	97.30%
Caco-2	+	0.7743	77.43%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8156	81.56%
OATP2B1 inhibitior	-	0.5773	57.73%
OATP1B1 inhibitior	+	0.9045	90.45%
OATP1B3 inhibitior	+	0.9738	97.38%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4502	45.02%
P-glycoprotein inhibitior	+	0.8189	81.89%
P-glycoprotein substrate	-	0.7522	75.22%
CYP3A4 substrate	+	0.5493	54.93%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.5571	55.71%
CYP2C9 inhibition	+	0.7766	77.66%
CYP2C19 inhibition	+	0.8962	89.62%
CYP2D6 inhibition	-	0.7334	73.34%
CYP1A2 inhibition	+	0.8679	86.79%
CYP2C8 inhibition	+	0.5951	59.51%
CYP inhibitory promiscuity	+	0.7750	77.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.9782	97.82%
Eye irritation	+	0.8653	86.53%
Skin irritation	-	0.6511	65.11%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	-	0.6164	61.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6655	66.55%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9410	94.10%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5874	58.74%
Acute Oral Toxicity (c)	III	0.5602	56.02%
Estrogen receptor binding	+	0.9015	90.15%
Androgen receptor binding	+	0.8533	85.33%
Thyroid receptor binding	+	0.6974	69.74%
Glucocorticoid receptor binding	+	0.8533	85.33%
Aromatase binding	+	0.7300	73.00%
PPAR gamma	+	0.7449	74.49%
Honey bee toxicity	-	0.8220	82.20%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5949	59.49%
Fish aquatic toxicity	+	0.8898	88.98%

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	97.50%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.99%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.17%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.12%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.47%	86.33%
CHEMBL2535	P11166	Glucose transporter	91.20%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.39%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.18%	99.17%
CHEMBL3194	P02766	Transthyretin	86.76%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.02%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.57%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	83.97%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	83.36%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.32%	96.95%
CHEMBL1255126	O15151	Protein Mdm4	82.04%	90.20%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.52%	80.78%
CHEMBL308	P06493	Cyclin-dependent kinase 1	80.89%	91.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.40%	85.14%

Plants that contains it

• Andrographis affinis
• Andrographis elongata
• Andrographis lineata
• Andrographis paniculata
• Andrographis rothii
• Lagochilus leiacanthus
• Limnophila indica
• Ruta graveolens
• Scutellaria baicalensis
• Scutellaria glabrata
• Scutellaria pekinensis var. pekinensis
• Scutellaria prostrata

Cross-Links

• PubChem: 5320399
• NPASS: NPC274909
• LOTUS: LTS0072996
• wikiData: Q27270850