Flavaspidic acid

Details

• Internal ID: c3a0532c-9170-463d-82dd-07bb08c45ba2
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 2-butanoyl-4-[(3-butanoyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
• SMILES (Canonical): CCCC(=O)C1=C(C(=C(C(=C1O)CC2=C(C(C(=O)C(=C2O)C(=O)CCC)(C)C)O)O)C)O
• SMILES (Isomeric): CCCC(=O)C1=C(C(=C(C(=C1O)CC2=C(C(C(=O)C(=C2O)C(=O)CCC)(C)C)O)O)C)O
• InChI: InChI=1S/C24H30O8/c1-6-8-14(25)16-19(28)11(3)18(27)12(20(16)29)10-13-21(30)17(15(26)9-7-2)23(32)24(4,5)22(13)31/h27-31H,6-10H2,1-5H3
• InChI Key: NHVQLOCTXSMKIX-UHFFFAOYSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₈
• Molecular Weight: 446.50 g/mol
• Exact Mass: 446.19406791 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• Toxifren
• 114-42-1
• Flavaspidic acid BB
• Glavaspidic acid
• Flavaspidsaeure
• Flavaspidsaeure [German]
• NSC 115497
• 2-butanoyl-4-[(3-butanoyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
• NSC-115497
• BRN 2068481
• UNII-7HFR949XW9
• 7HFR949XW9
• NSC115497
• 4-08-00-03748 (Beilstein Handbook Reference)
• Butyrophenone, 3'-((5-butyryl-2,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadien-1-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-
• 2,5-Cyclohexadien-1-one, 3,5-dihydroxy-4,4-dimethyl-2-(1-oxobutyl)-6-((2,4,6-trihydroxy-3-methyl-5-(1-oxobutyl)phenyl)methyl)-
• 3'-((5-Butyryl-2,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadien-1-yl)methyl)-5'-methylphloro butyrophenone
• 2,5-Cyclohexadien-1-one, 3,5-dihydroxy-4,4-dimethyl-2-(1-oxobutyl)-6-[[2,4,6-trihydroxy-3-methyl-5-(1-oxobutyl)phenyl]methyl]-
• FLAVASPIDIC ACID [MI]
• CHEMBL291819
• SCHEMBL1785484
• DTXSID90878659
• LS-48299
• NCI60_000345
• FLAVASPIDIC ACID .BETA.-FORM [MI]
• FLAVASPIDIC ACID .ALPHA.-FORM [MI]
• Q5458045
• WLN: L6V DHJ BV3 CQ D1 D1 EQ F1R BQ DQ FQ C1 EV3
• 2, 3,5-dihydroxy-4,4-dimethyl-2-(1-oxobutyl)-6-[[2,4,6-trihydroxy-3-methyl-5-(1-oxobutyl)phenyl]methyl]-
• 2-butanoyl-6-[(3-butanoyl-2,4,6-trihydroxy-5-methyl-phenyl)methyl]-3,5-dihydroxy-4,4-dimethyl-cyclohexa-2,5-dien-1-one
• 3,5-DIHYDROXY-4,4-DIMETHYL-2-(1-OXOBUTYL)-6-((2,4,6-TRIHYDROXY-3-METHYL-5-(1-OXOBUTYL)PHENYL)METHYL)-2,5-CYCLOHEXADIEN-1-ONE
• Butyrophenone,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadien-1-yl)methyl]-2',4',6'-trihydroxy-5'-methyl-
• PHLOROBUTYROPHENONE, 3'-((5-BUTYRYL-2,4-DIHYDROXY-3,3-DIMETHYL-6-OXO-1,4-CYCLOHEXADIEN-1-YL)METHYL)-5'-METHYL-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9848	98.48%
Caco-2	-	0.5337	53.37%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8433	84.33%
OATP2B1 inhibitior	-	0.7122	71.22%
OATP1B1 inhibitior	-	0.3476	34.76%
OATP1B3 inhibitior	+	0.9009	90.09%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5361	53.61%
P-glycoprotein inhibitior	-	0.6992	69.92%
P-glycoprotein substrate	-	0.7651	76.51%
CYP3A4 substrate	+	0.5711	57.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8470	84.70%
CYP3A4 inhibition	+	0.5074	50.74%
CYP2C9 inhibition	+	0.7327	73.27%
CYP2C19 inhibition	+	0.6645	66.45%
CYP2D6 inhibition	-	0.7989	79.89%
CYP1A2 inhibition	+	0.5589	55.89%
CYP2C8 inhibition	-	0.6548	65.48%
CYP inhibitory promiscuity	+	0.7062	70.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8477	84.77%
Carcinogenicity (trinary)	Non-required	0.6564	65.64%
Eye corrosion	-	0.9873	98.73%
Eye irritation	+	0.6174	61.74%
Skin irritation	-	0.7249	72.49%
Skin corrosion	-	0.9083	90.83%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7323	73.23%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5836	58.36%
skin sensitisation	-	0.5282	52.82%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4866	48.66%
Acute Oral Toxicity (c)	III	0.6087	60.87%
Estrogen receptor binding	+	0.7724	77.24%
Androgen receptor binding	-	0.6473	64.73%
Thyroid receptor binding	+	0.5681	56.81%
Glucocorticoid receptor binding	+	0.6726	67.26%
Aromatase binding	+	0.5926	59.26%
PPAR gamma	+	0.5878	58.78%
Honey bee toxicity	-	0.9411	94.11%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9945	99.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	93.46%	90.17%
CHEMBL2581	P07339	Cathepsin D	92.04%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.36%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.37%	95.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.64%	89.34%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.01%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.84%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.07%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.93%	94.45%
CHEMBL230	P35354	Cyclooxygenase-2	80.37%	89.63%

Plants that contains it

• Alhagi maurorum
• Camellia sinensis
• Dryopteris aitoniana
• Dryopteris crassirhizoma

Cross-Links

• PubChem: 8237
• NPASS: NPC66252
• LOTUS: LTS0069934
• wikiData: Q5458045