Protoapigenone

Details

• Internal ID: 7ab362e2-dc38-4a82-9625-8915ac43c1c5
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones
• IUPAC Name: 5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)chromen-4-one
• SMILES (Canonical): C1=CC(C=CC1=O)(C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O
• SMILES (Isomeric): C1=CC(C=CC1=O)(C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O
• InChI: InChI=1S/C15H10O6/c16-8-1-3-15(20,4-2-8)13-7-11(19)14-10(18)5-9(17)6-12(14)21-13/h1-7,17-18,20H
• InChI Key: DLMOVPAUHQQYHA-UHFFFAOYSA-N
• Popularity: 30 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.24 g/mol
• Exact Mass: 286.04773803 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• MLS000574831
• SMR000156275
• 5,7-Dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)-4H-chromen-4-one
• 5,7-dihydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)chromen-4-one
• 862884-32-0
• CHEMBL414890
• SCHEMBL13066080
• BDBM43766
• cid_11644907
• REGID_for_CID_11644907
• 5,7-dihydroxy-2-(1-hydroxy-4-keto-cyclohexa-2,5-dien-1-yl)chromone
• 5,7-bis(oxidanyl)-2-(1-oxidanyl-4-oxidanylidene-cyclohexa-2,5-dien-1-yl)chromen-4-one
• 5,7-dihydroxy-2-(1-hydroxy-4-oxo-1-cyclohexa-2,5-dienyl)-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9522	95.22%
Caco-2	-	0.6968	69.68%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5803	58.03%
OATP2B1 inhibitior	-	0.6765	67.65%
OATP1B1 inhibitior	+	0.9327	93.27%
OATP1B3 inhibitior	+	0.9623	96.23%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7790	77.90%
P-glycoprotein inhibitior	-	0.8600	86.00%
P-glycoprotein substrate	-	0.8427	84.27%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	0.6038	60.38%
CYP2D6 substrate	-	0.8671	86.71%
CYP3A4 inhibition	+	0.8505	85.05%
CYP2C9 inhibition	+	0.6597	65.97%
CYP2C19 inhibition	-	0.7032	70.32%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	-	0.6869	68.69%
CYP2C8 inhibition	-	0.6151	61.51%
CYP inhibitory promiscuity	+	0.5334	53.34%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5154	51.54%
Eye corrosion	-	0.9868	98.68%
Eye irritation	+	0.8071	80.71%
Skin irritation	-	0.6067	60.67%
Skin corrosion	-	0.9474	94.74%
Ames mutagenesis	+	0.6436	64.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.8997	89.97%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8334	83.34%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4604	46.04%
Acute Oral Toxicity (c)	III	0.5514	55.14%
Estrogen receptor binding	+	0.9267	92.67%
Androgen receptor binding	+	0.8330	83.30%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.9491	94.91%
Aromatase binding	+	0.9030	90.30%
PPAR gamma	+	0.9194	91.94%
Honey bee toxicity	-	0.8307	83.07%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9282	92.82%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	31622.8 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	35481.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	3981.1 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	31622.8 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	1412.5 nM	Potency	via CMAUP
CHEMBL1741176	P17861	X-box-binding protein 1	3840 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.07%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.41%	89.00%
CHEMBL3194	P02766	Transthyretin	90.84%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.97%	96.12%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.43%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.37%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.17%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.32%	91.49%
CHEMBL4208	P20618	Proteasome component C5	85.15%	90.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.42%	91.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.09%	99.23%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.17%	94.42%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.90%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	80.17%	94.73%

Plants that contains it

• Daphne oleoides
• Macrothelypteris torresiana

Cross-Links

• PubChem: 11644907
• NPASS: NPC160972
• ChEMBL: CHEMBL414890
• LOTUS: LTS0111822
• wikiData: Q104984464