Diospongin A

Details

• Internal ID: 2bcb490a-31e9-47e5-a848-6fa2c072ce9e
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: 2-[(2R,4S,6S)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone
• SMILES (Canonical): C1C(CC(OC1CC(=O)C2=CC=CC=C2)C3=CC=CC=C3)O
• SMILES (Isomeric): C1[C@@H](C[C@H](O[C@H]1CC(=O)C2=CC=CC=C2)C3=CC=CC=C3)O
• InChI: InChI=1S/C19H20O3/c20-16-11-17(13-18(21)14-7-3-1-4-8-14)22-19(12-16)15-9-5-2-6-10-15/h1-10,16-17,19-20H,11-13H2/t16-,17+,19-/m0/s1
• InChI Key: HQTSVUPKAYCDEB-SCTDSRPQSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₃
• Molecular Weight: 296.40 g/mol
• Exact Mass: 296.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.54
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 791104-63-7
• DTXSID601142609
• 2-[(2R,4S,6S)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone
• 1-Phenyl-2-[(2R,4S,6S)-tetrahydro-4-hydroxy-6-phenyl-2H-pyran-2-yl]ethanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9837	98.37%
Caco-2	+	0.7866	78.66%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8441	84.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9036	90.36%
OATP1B3 inhibitior	+	0.9695	96.95%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7126	71.26%
P-glycoprotein inhibitior	-	0.7790	77.90%
P-glycoprotein substrate	-	0.8997	89.97%
CYP3A4 substrate	-	0.6275	62.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6912	69.12%
CYP3A4 inhibition	-	0.7596	75.96%
CYP2C9 inhibition	-	0.7523	75.23%
CYP2C19 inhibition	+	0.6912	69.12%
CYP2D6 inhibition	-	0.9144	91.44%
CYP1A2 inhibition	-	0.8414	84.14%
CYP2C8 inhibition	+	0.4822	48.22%
CYP inhibitory promiscuity	-	0.7368	73.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8213	82.13%
Carcinogenicity (trinary)	Non-required	0.6235	62.35%
Eye corrosion	-	0.9819	98.19%
Eye irritation	+	0.5692	56.92%
Skin irritation	-	0.5431	54.31%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3770	37.70%
Micronuclear	+	0.5218	52.18%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8754	87.54%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.5744	57.44%
Acute Oral Toxicity (c)	III	0.6472	64.72%
Estrogen receptor binding	+	0.6221	62.21%
Androgen receptor binding	-	0.6091	60.91%
Thyroid receptor binding	-	0.7133	71.33%
Glucocorticoid receptor binding	-	0.7512	75.12%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.6283	62.83%
Honey bee toxicity	-	0.9366	93.66%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.3954	39.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	93.00%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.83%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.56%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.49%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.02%	96.09%
CHEMBL5028	O14672	ADAM10	83.21%	97.50%

Plants that contains it

• Dioscorea spongiosa

Cross-Links

• PubChem: 11652299
• LOTUS: LTS0007130
• wikiData: Q104400169