Japonicin A

Details

• Internal ID: c5ac9ae0-be68-45a4-a2d1-6d78ae66f916
• Taxonomy: Organic acids and derivatives > Vinylogous acids
• IUPAC Name: 4-[[2,6-dihydroxy-3,3-dimethyl-5-(2-methylpropanoyl)-4-oxocyclohexa-1,5-dien-1-yl]methyl]-3,5-dihydroxy-6,6-dimethyl-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C(=C(C(C1=O)(C)C)O)CC2=C(C(C(=O)C(=C2O)C(=O)C(C)C)(C)C)O)O
• SMILES (Isomeric): CC(C)C(=O)C1=C(C(=C(C(C1=O)(C)C)O)CC2=C(C(C(=O)C(=C2O)C(=O)C(C)C)(C)C)O)O
• InChI: InChI=1S/C25H32O8/c1-10(2)16(26)14-18(28)12(20(30)24(5,6)22(14)32)9-13-19(29)15(17(27)11(3)4)23(33)25(7,8)21(13)31/h10-11,28-31H,9H2,1-8H3
• InChI Key: HOKPFFGRILZRLX-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₈
• Molecular Weight: 460.50 g/mol
• Exact Mass: 460.20971797 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 4.29
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• NSC611465
• NSC-611465
• 4-[[2,6-dihydroxy-3,3-dimethyl-5-(2-methylpropanoyl)-4-oxocyclohexa-1,5-dien-1-yl]methyl]-3,5-dihydroxy-6,6-dimethyl-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9722	97.22%
Caco-2	-	0.7225	72.25%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8196	81.96%
OATP2B1 inhibitior	-	0.5718	57.18%
OATP1B1 inhibitior	+	0.8578	85.78%
OATP1B3 inhibitior	+	0.9143	91.43%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5212	52.12%
P-glycoprotein inhibitior	-	0.5906	59.06%
P-glycoprotein substrate	-	0.9344	93.44%
CYP3A4 substrate	-	0.5491	54.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8694	86.94%
CYP3A4 inhibition	-	0.8634	86.34%
CYP2C9 inhibition	-	0.5417	54.17%
CYP2C19 inhibition	-	0.6842	68.42%
CYP2D6 inhibition	-	0.9189	91.89%
CYP1A2 inhibition	-	0.8595	85.95%
CYP2C8 inhibition	-	0.9671	96.71%
CYP inhibitory promiscuity	-	0.5313	53.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7993	79.93%
Carcinogenicity (trinary)	Non-required	0.6215	62.15%
Eye corrosion	-	0.9783	97.83%
Eye irritation	-	0.5417	54.17%
Skin irritation	-	0.6704	67.04%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4125	41.25%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6584	65.84%
skin sensitisation	+	0.6416	64.16%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.7438	74.38%
Acute Oral Toxicity (c)	III	0.6176	61.76%
Estrogen receptor binding	+	0.7745	77.45%
Androgen receptor binding	-	0.5332	53.32%
Thyroid receptor binding	+	0.6661	66.61%
Glucocorticoid receptor binding	+	0.5611	56.11%
Aromatase binding	-	0.5112	51.12%
PPAR gamma	+	0.6704	67.04%
Honey bee toxicity	-	0.9112	91.12%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.9711	97.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.25%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.42%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.26%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	80.02%	90.17%

Plants that contains it

• Hypericum brasiliense

Cross-Links

• PubChem: 356268
• LOTUS: LTS0129125
• wikiData: Q105031341