Skullcapflavone II

Details

• Internal ID: f4660b4b-81bf-4b85-a2f4-e8498d0c5d94
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-2-(2-hydroxy-6-methoxyphenyl)-6,7,8-trimethoxychromen-4-one
• SMILES (Canonical): COC1=CC=CC(=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
• SMILES (Isomeric): COC1=CC=CC(=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
• InChI: InChI=1S/C19H18O8/c1-23-11-7-5-6-9(20)13(11)12-8-10(21)14-15(22)17(24-2)19(26-4)18(25-3)16(14)27-12/h5-8,20,22H,1-4H3
• InChI Key: GMQFOKBGMKVUQZ-UHFFFAOYSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.10016753 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Neobaicalein
• 55084-08-7
• Scullcapflavone II
• 5,2'-Dihydroxy-6,7,8,6'-tetramethoxyflavone
• CHEBI:9061
• BV62EAN2VM
• 5-hydroxy-2-(2-hydroxy-6-methoxyphenyl)-6,7,8-trimethoxychromen-4-one
• 5-hydroxy-2-(2-hydroxy-6-methoxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 5-hydroxy-2-(2-hydroxy-6-methoxyphenyl)-6,7,8-trimethoxy-
• 5-hydroxy-2-(2-hydroxy-6-methoxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-one
• Skullcapflavon II
• UNII-BV62EAN2VM
• 5,2'-dihydroxy-6,7,8,6'-tetramethoxy-flavone
• CHEMBL465561
• SCHEMBL3960981
• DTXSID10203606
• HY-N6624
• BDBM50478454
• LMPK12111423
• NSC717846
• AKOS040760119
• NSC-717846
• AC-31924
• MS-26043
• NCI60_040650
• Skullcapflavone II, >=90% (LC/MS-UV)
• CS-0034412
• FT-0776595
• E88602
• 2',5-DIHYDROXY-6,6',7,8-TETRAMETHOXYFLAVONE
• 5,6'-DIHYDROXY-6,7,8,2'-TETRAMETHOXYFLAVONE
• Q27108257
• 5-hydroxy-2-(2-hydroxy-6-methoxy-phenyl)-6,7,8-trimethoxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	+	0.7017	70.17%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7936	79.36%
OATP2B1 inhibitior	-	0.7195	71.95%
OATP1B1 inhibitior	+	0.9156	91.56%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5311	53.11%
P-glycoprotein inhibitior	+	0.8160	81.60%
P-glycoprotein substrate	-	0.7935	79.35%
CYP3A4 substrate	+	0.5483	54.83%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.7237	72.37%
CYP2C9 inhibition	-	0.6863	68.63%
CYP2C19 inhibition	+	0.6566	65.66%
CYP2D6 inhibition	-	0.8329	83.29%
CYP1A2 inhibition	+	0.8642	86.42%
CYP2C8 inhibition	+	0.5977	59.77%
CYP inhibitory promiscuity	+	0.7231	72.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5851	58.51%
Eye corrosion	-	0.9825	98.25%
Eye irritation	+	0.6583	65.83%
Skin irritation	-	0.7275	72.75%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5935	59.35%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9511	95.11%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6283	62.83%
Acute Oral Toxicity (c)	III	0.4741	47.41%
Estrogen receptor binding	+	0.8650	86.50%
Androgen receptor binding	+	0.7076	70.76%
Thyroid receptor binding	+	0.7702	77.02%
Glucocorticoid receptor binding	+	0.7997	79.97%
Aromatase binding	+	0.6652	66.52%
PPAR gamma	+	0.7676	76.76%
Honey bee toxicity	-	0.8797	87.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8969	89.69%

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	98.77%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.94%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.97%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.88%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.64%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.93%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.05%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	88.26%	94.73%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	88.24%	94.03%
CHEMBL2535	P11166	Glucose transporter	88.21%	98.75%
CHEMBL3194	P02766	Transthyretin	86.56%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.35%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.92%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	84.63%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.15%	99.17%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	80.44%	98.11%

Plants that contains it

• Lagochilus leiacanthus
• Lawrencella rosea
• Parinari campestris
• Prunus persica
• Scutellaria alpina
• Scutellaria amoena
• Scutellaria baicalensis
• Scutellaria guatemalensis
• Scutellaria viscidula
• Stizophyllum riparium
• Utricularia vulgaris
• Vincetoxicum amplexicaule

Cross-Links

• PubChem: 124211
• NPASS: NPC92659
• LOTUS: LTS0213690
• wikiData: Q27108257