Desaspidin

Details

• Internal ID: 61a22b57-7348-4f36-b8fb-440b2e285c28
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 2-butanoyl-4-[(3-butanoyl-2,4-dihydroxy-6-methoxyphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
• SMILES (Canonical): CCCC(=O)C1=C(C(=C(C=C1O)OC)CC2=C(C(C(=O)C(=C2O)C(=O)CCC)(C)C)O)O
• SMILES (Isomeric): CCCC(=O)C1=C(C(=C(C=C1O)OC)CC2=C(C(C(=O)C(=C2O)C(=O)CCC)(C)C)O)O
• InChI: InChI=1S/C24H30O8/c1-6-8-14(25)18-16(27)11-17(32-5)12(20(18)28)10-13-21(29)19(15(26)9-7-2)23(31)24(3,4)22(13)30/h11,27-30H,6-10H2,1-5H3
• InChI Key: XDIZFCKCCMUFFG-UHFFFAOYSA-N
• Popularity: 83 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₈
• Molecular Weight: 446.50 g/mol
• Exact Mass: 446.19406791 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.23
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

• Desaspidin BB
• Rosapin
• Desaspidin [INN]
• 114-43-2
• KV3495SGKS
• 60842-45-7
• Desaspidin (INN)
• 2-butanoyl-4-[(3-butanoyl-2,4-dihydroxy-6-methoxyphenyl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
• 3'-((5-Butyryl-2,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadien-1-yl)methyl)-2',6'-dihydroxy-4'-methoxybutyrophenone
• Butyrophenone, 3'-((5-butyryl-2,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadien-1-yl)methyl)-2',6'-dihydroxy-4'-methoxy-
• Desaspidina
• Desaspidine
• Desaspidinum
• Desapidin
• Desaspidine [INN-French]
• Desaspidinum [INN-Latin]
• Desaspidina [INN-Spanish]
• 2,5-Cyclohexadien-1-one, 2-((2,4-dihydroxy-6-methoxy-3-(1-oxobutyl)phenyl)methyl)-3,5-dihydroxy-4,4-dimethyl-6-(1-oxobutyl)-
• EINECS 204-048-5
• UNII-KV3495SGKS
• BRN 2068482
• Deaspidin
• 2,5-Cyclohexadien-1-one, 2-[[2,4-dihydroxy-6-methoxy-3-(1-oxobutyl)phenyl]methyl]-3,5-dihydroxy-4,4-dimethyl-6-(1-oxobutyl)-
• 3'-[(5-Butyryl-2,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadien-1-yl)methyl]-2',6'-dihydroxy-4'-methoxybutyrophenone
• DESASPIDIN BB [MI]
• DESASPIDIN [WHO-DD]
• 4-08-00-03747 (Beilstein Handbook Reference)
• SCHEMBL2732746
• CHEMBL2105606
• DTXSID6074461
• DTXSID00976317
• CHEBI:135960
• GAHOBHHMYUYJDT-UHFFFAOYSA-N
• DB13567
• D07365
• Q904668
• 2-Butyryl-6-(3-butyryl-2,4-dihydroxy-6-methoxybenzyl)-3,5-dihydroxy-4,4-dimethyl-2,5-cyclohexadien-1-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9843	98.43%
Caco-2	+	0.4918	49.18%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8505	85.05%
OATP2B1 inhibitior	-	0.5745	57.45%
OATP1B1 inhibitior	+	0.7847	78.47%
OATP1B3 inhibitior	+	0.8878	88.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7891	78.91%
P-glycoprotein inhibitior	-	0.6175	61.75%
P-glycoprotein substrate	-	0.6334	63.34%
CYP3A4 substrate	+	0.6019	60.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8268	82.68%
CYP3A4 inhibition	-	0.5598	55.98%
CYP2C9 inhibition	+	0.7546	75.46%
CYP2C19 inhibition	+	0.7298	72.98%
CYP2D6 inhibition	-	0.7903	79.03%
CYP1A2 inhibition	+	0.6079	60.79%
CYP2C8 inhibition	+	0.6561	65.61%
CYP inhibitory promiscuity	+	0.7093	70.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8321	83.21%
Carcinogenicity (trinary)	Non-required	0.6681	66.81%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.6815	68.15%
Skin irritation	-	0.7783	77.83%
Skin corrosion	-	0.9362	93.62%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7990	79.90%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6688	66.88%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6490	64.90%
Acute Oral Toxicity (c)	III	0.5538	55.38%
Estrogen receptor binding	+	0.7995	79.95%
Androgen receptor binding	-	0.6153	61.53%
Thyroid receptor binding	+	0.6087	60.87%
Glucocorticoid receptor binding	+	0.7367	73.67%
Aromatase binding	+	0.7502	75.02%
PPAR gamma	+	0.6206	62.06%
Honey bee toxicity	-	0.8694	86.94%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9903	99.03%

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	98.61%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.89%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.06%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.16%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.90%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.74%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.47%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.46%	86.33%
CHEMBL1255126	O15151	Protein Mdm4	84.44%	90.20%
CHEMBL4040	P28482	MAP kinase ERK2	84.12%	83.82%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.78%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.41%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.38%	92.94%
CHEMBL4208	P20618	Proteasome component C5	82.37%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.31%	92.62%

Plants that contains it

• Dryopteris campyloptera
• Dryopteris cristata
• Dryopteris expansa

Cross-Links

• PubChem: 8238
• LOTUS: LTS0154385
• wikiData: Q904668