Filicinic acid

Details

• Internal ID: 87680738-8009-4062-9101-abf85d86c461
• Taxonomy: Organic acids and derivatives > Vinylogous acids
• IUPAC Name: 3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
• SMILES (Canonical): CC1(C(=CC(=CC1=O)O)O)C
• SMILES (Isomeric): CC1(C(=CC(=CC1=O)O)O)C
• InChI: InChI=1S/C8H10O3/c1-8(2)6(10)3-5(9)4-7(8)11/h3-4,9-10H,1-2H3
• InChI Key: ZAQQZMZXYOTJAB-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 154.16 g/mol
• Exact Mass: 154.062994177 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.48
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 2065-00-1
• 3,5-Dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one
• 2,5-Cyclohexadien-1-one, 3,5-dihydroxy-4,4-dimethyl-
• Filicinsaure
• 3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
• SCHEMBL3482759
• CHEBI:71593
• DTXSID20879159
• ZITLVRQXJUFZOO-UHFFFAOYSA-N
• Q27139738
• 3,5-Dihydroxy-4,4-dimethyl-2,5-cyclohexadien-1-one #
• 3,5-dihydroxy-4,4-dimethyl-cyclohexa-2,5-dien-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	+	0.9009	90.09%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8391	83.91%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.8860	88.60%
OATP1B3 inhibitior	+	0.9771	97.71%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	-	0.9248	92.48%
P-glycoprotein inhibitior	-	0.9747	97.47%
P-glycoprotein substrate	-	0.9847	98.47%
CYP3A4 substrate	-	0.6393	63.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8859	88.59%
CYP3A4 inhibition	-	0.8066	80.66%
CYP2C9 inhibition	-	0.5610	56.10%
CYP2C19 inhibition	-	0.7309	73.09%
CYP2D6 inhibition	-	0.9349	93.49%
CYP1A2 inhibition	-	0.7630	76.30%
CYP2C8 inhibition	-	0.9809	98.09%
CYP inhibitory promiscuity	-	0.6792	67.92%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7550	75.50%
Carcinogenicity (trinary)	Non-required	0.6569	65.69%
Eye corrosion	-	0.7389	73.89%
Eye irritation	+	0.9774	97.74%
Skin irritation	+	0.6848	68.48%
Skin corrosion	-	0.7009	70.09%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7718	77.18%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.6959	69.59%
skin sensitisation	+	0.7853	78.53%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.7571	75.71%
Nephrotoxicity	+	0.7582	75.82%
Acute Oral Toxicity (c)	III	0.7669	76.69%
Estrogen receptor binding	-	0.8029	80.29%
Androgen receptor binding	-	0.7468	74.68%
Thyroid receptor binding	-	0.7059	70.59%
Glucocorticoid receptor binding	-	0.6947	69.47%
Aromatase binding	-	0.8261	82.61%
PPAR gamma	-	0.7455	74.55%
Honey bee toxicity	-	0.9549	95.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8523	85.23%

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	94.80%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.00%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.51%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.65%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.44%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.39%	85.14%

Plants that contains it

• Dryopteris crassirhizoma

Cross-Links

• PubChem: 550690
• NPASS: NPC68298