Radicinin

Details

• Internal ID: 600ec693-7f5f-4302-9300-5d662a7463a5
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Aryl ketones > Aryl alkyl ketones
• IUPAC Name: (2S,3S)-3-hydroxy-2-methyl-7-[(E)-prop-1-enyl]-2,3-dihydropyrano[3,2-c]pyran-4,5-dione
• SMILES (Canonical): CC=CC1=CC2=C(C(=O)C(C(O2)C)O)C(=O)O1
• SMILES (Isomeric): C/C=C/C1=CC2=C(C(=O)[C@H]([C@@H](O2)C)O)C(=O)O1
• InChI: InChI=1S/C12H12O5/c1-3-4-7-5-8-9(12(15)17-7)11(14)10(13)6(2)16-8/h3-6,10,13H,1-2H3/b4-3+/t6-,10-/m0/s1
• InChI Key: SDKXGAICTNHFCN-DCJAWTJCSA-N
• Popularity: 26 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.22 g/mol
• Exact Mass: 236.06847348 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.00
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Stemphylone
• 10088-95-6
• Radicinin (VAN)
• NSC118343
• NSC 118343
• UNII-G01Z2N575M
• CCRIS 8483
• G01Z2N575M
• (2S,3S)-3-hydroxy-2-methyl-7-[(E)-prop-1-enyl]-2,3-dihydropyrano[3,2-c]pyran-4,5-dione
• NSC-118343
• 1402-20-6
• 2,3-Dihydro-3-alpha-hydroxy-2-beta-methyl-7-propenyl-4H,5H-pyrano(4,3-b)pyran-4,5-dione
• 4H,5H-Pyrano(4,3-b)pyran-4,5-dione, 2,3-dihydro-3-alpha-hydroxy-2-beta-methyl-7-propenyl-
• MLS002706791
• RADICININ [MI]
• SCHEMBL1531040
• SCHEMBL1531042
• CHEMBL1994984
• DTXSID70871946
• CHEBI:183741
• AKOS040747350
• 2,5H-pyrano[4,3-b]pyran-4,5-dione
• HY-113816
• LS-127484
• CS-0062918
• WLN: T66 BVO GO JV&TJ D1U2 H1 IQ
• Q27278392
• (2S,3S)-3-hydroxy-2-methyl-7-[(E)-prop-1-enyl]-2,3-dihydropyrano[4,3-b]pyran-4,5-dione
• 4H,3-b]pyran-4,5-dione, 2,3-dihydro-3.alpha.-hydroxy-2.beta.-methyl-7-propenyl-
• (2S,3S)-3-hydroxy-2-methyl-7-((E)-prop-1-en-1-yl)-2,3-dihydro-4H,5H-pyrano[4,3-b]pyran-4,5-dione
• (2S,3S)-3-Hydroxy-2-methyl-7-[(1E)-prop-1-en-1-yl]-2,3-dihydro-4H,5H-pyrano[4,3-b]pyran-4,5-dione
• [2S-[2alpha,3beta,7(E)]]-2,3-Dihydro-3-hydroxy-2-methyl-7-(1-propenyl)-4H,5H-pyrano[4,3-b]pyran-4,5-dione
• 2H-PYRAN-5-CARBOXYLIC ACID, 3,4-DIHYDRO-3-HYDROXY-6-(2-HYDROXY-1,3-PENTADIENYL)-2-METHYL-4-OXO-, .DELTA.-LACTONE
• 4H,3-b]pyran-4,5-dione, 2,3-dihydro-3-hydroxy-2-methyl-7-(1-propenyl)-, [2S-[2.alpha.,3.beta.,7(E)]]-
• 4H,5H-PYRANO(4,3-B)PYRAN-4,5-DIONE, 2,3-DIHYDRO-3-HYDROXY-2-METHYL-7-((1E)-1-PROPEN-1-YL)-, (2S,3S)-
• 4H,5H-Pyrano[4,3-b]pyran-4,5-dione, 2,3-dihydro-3-hydroxy-2-methyl-7-(1-propenyl)-, [2S-[2.alpha.,3.beta.,7(E)]]-
• 4H,5H-Pyrano[4,3-b]pyran-4,5-dione, 2,3-dihydro-3.alpha.-hydroxy-2.beta.-methyl-7-propenyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9684	96.84%
Caco-2	-	0.6828	68.28%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7316	73.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8859	88.59%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9340	93.40%
P-glycoprotein inhibitior	-	0.9160	91.60%
P-glycoprotein substrate	-	0.8607	86.07%
CYP3A4 substrate	-	0.5664	56.64%
CYP2C9 substrate	-	0.6095	60.95%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.7586	75.86%
CYP2C9 inhibition	-	0.7156	71.56%
CYP2C19 inhibition	-	0.8830	88.30%
CYP2D6 inhibition	-	0.9429	94.29%
CYP1A2 inhibition	-	0.8377	83.77%
CYP2C8 inhibition	-	0.8929	89.29%
CYP inhibitory promiscuity	-	0.8291	82.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4644	46.44%
Eye corrosion	-	0.9740	97.40%
Eye irritation	-	0.5070	50.70%
Skin irritation	+	0.5450	54.50%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6120	61.20%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.7146	71.46%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6087	60.87%
Acute Oral Toxicity (c)	II	0.6753	67.53%
Estrogen receptor binding	+	0.5974	59.74%
Androgen receptor binding	+	0.5989	59.89%
Thyroid receptor binding	-	0.8532	85.32%
Glucocorticoid receptor binding	-	0.4907	49.07%
Aromatase binding	-	0.5793	57.93%
PPAR gamma	+	0.5995	59.95%
Honey bee toxicity	-	0.8985	89.85%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9623	96.23%

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	94.45%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.11%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.60%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.21%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.54%	94.73%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.72%	94.80%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.13%	89.34%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.71%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.93%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.34%	90.71%

Plants that contains it

• Panzerina lanata

Cross-Links

• PubChem: 5381458
• NPASS: NPC274075
• LOTUS: LTS0124933
• wikiData: Q27278392