Osajin

Details

• Internal ID: fc5a4643-9c8d-4383-bdc1-4ea3c807ee56
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC(=CCC1=C2C(=C3C(=C1O)C(=O)C(=CO3)C4=CC=C(C=C4)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C3C(=C1O)C(=O)C(=CO3)C4=CC=C(C=C4)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C25H24O5/c1-14(2)5-10-17-21(27)20-22(28)19(15-6-8-16(26)9-7-15)13-29-24(20)18-11-12-25(3,4)30-23(17)18/h5-9,11-13,26-27H,10H2,1-4H3
• InChI Key: DCTLJGWMHPGCOS-UHFFFAOYSA-N
• Popularity: 44 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₅
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.16237386 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.56
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 482-53-1
• UNII-83R5N9X74B
• CHEBI:7797
• 83R5N9X74B
• NSC21565
• NSC 21565
• NSC-21565
• 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
• 4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-
• 4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)- (8CI)
• 3'-DEOXYPOMIFERIN
• 5'-O-DEMETHYLSCANDINONE
• 1-adamantylmethacrylate
• Spectrum_000234
• SpecPlus_000197
• OSAJIN [INCI]
• Spectrum2_000175
• Spectrum3_000225
• Spectrum4_001527
• Spectrum5_000034
• OSAJIN [MI]
• Oprea1_003228
• Oprea1_066678
• BSPBio_001869
• KBioGR_001934
• KBioSS_000714
• SPECTRUM201595
• MLS001049118
• DivK1c_006293
• SCHEMBL571689
• SPBio_000069
• CHEMBL238188
• MEGxp0_001415
• ACon1_002463
• KBio1_001237
• KBio2_000714
• KBio2_003282
• KBio2_005850
• KBio3_001369
• DTXSID10964028
• HMS2269P11
• C25H24O5
• EX-A4870
• HY-N3125
• BDBM50442397
• CCG-38383
• LMPK12050201
• STK396323
• Osajin, >=95% (LC/MS-ELSD)
• AKOS000546821
• SDCCGMLS-0066875.P001
• NCGC00095510-01
• NCGC00095510-02
• NCGC00095510-03
• NCGC00169822-01
• NCGC00169822-02
• AC-36736
• MS-26916
• SMR000386948
• CS-0023313
• FT-0755262
• SR-01000738732
• SR-01000738732-2
• BRD-K01836637-001-03-6
• BRD-K01836637-001-12-7
• Q27107586
• B0005-142884
• 4H,2-b:3,4-b']dipyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-
• 4H,2-b:3,4-b']dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-
• 4H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-4-ONE, 5-HYDROXY-3-(4-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTEN-1-YL)-
• 4H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-4-ONE, 5-HYDROXY-3-(4-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTENYL)-
• 4H,8H-BENZO(1,2-B:3,4-B)DIPYRAN-4-ONE, 5-HYDROXY-3-(P-HYDROXYPHENYL)-8,8-DIMETHYL-6-(3-METHYL-2-BUTENYL)-
• 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-4H,8H-pyrano[2,3-f]chromen-4-one
• 5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
• 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-f]chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8383	83.83%
OATP2B1 inhibitior	-	0.5745	57.45%
OATP1B1 inhibitior	+	0.9272	92.72%
OATP1B3 inhibitior	+	0.9022	90.22%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8670	86.70%
P-glycoprotein inhibitior	+	0.7795	77.95%
P-glycoprotein substrate	-	0.6146	61.46%
CYP3A4 substrate	+	0.6434	64.34%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8144	81.44%
CYP3A4 inhibition	-	0.8433	84.33%
CYP2C9 inhibition	+	0.9362	93.62%
CYP2C19 inhibition	+	0.9285	92.85%
CYP2D6 inhibition	-	0.9065	90.65%
CYP1A2 inhibition	-	0.6721	67.21%
CYP2C8 inhibition	+	0.7234	72.34%
CYP inhibitory promiscuity	+	0.8410	84.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6496	64.96%
Eye corrosion	-	0.9918	99.18%
Eye irritation	+	0.5994	59.94%
Skin irritation	-	0.7358	73.58%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5637	56.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7259	72.59%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.5071	50.71%
skin sensitisation	-	0.7271	72.71%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6470	64.70%
Acute Oral Toxicity (c)	III	0.6759	67.59%
Estrogen receptor binding	+	0.9346	93.46%
Androgen receptor binding	+	0.8612	86.12%
Thyroid receptor binding	+	0.7167	71.67%
Glucocorticoid receptor binding	+	0.8228	82.28%
Aromatase binding	+	0.7414	74.14%
PPAR gamma	+	0.8992	89.92%
Honey bee toxicity	-	0.7511	75.11%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9945	99.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	15848.9 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	15848.9 nM	Potency	via CMAUP
CHEMBL5514	P42858	Huntingtin	15848.9 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	12589.3 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	25118.9 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	19952.6 nM; 22387.2 nM; 31622.8 nM; 3162.3 nM; 7079.5 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	10000 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	via CMAUP
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	23600 nM	IC50	PMID: 26704263
CHEMBL1293232	Q16637	Survival motor neuron protein	19952.6 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.15%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.37%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.93%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.82%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	91.76%	94.75%
CHEMBL3038469	P24941	CDK2/Cyclin A	91.73%	91.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.34%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.35%	91.71%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.74%	97.28%
CHEMBL3401	O75469	Pregnane X receptor	88.00%	94.73%
CHEMBL242	Q92731	Estrogen receptor beta	87.65%	98.35%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.85%	93.10%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.53%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.45%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.29%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	82.74%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.53%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.06%	99.15%

Plants that contains it

• Brachypterum scandens
• Deguelia hatschbachii
• Deguelia scandens
• Erythrina variegata
• Euchresta horsfieldii
• Euchresta japonica
• Euphorbia micractina
• Flemingia macrophylla
• Flemingia prostrata
• Maackia floribunda
• Maclura pomifera
• Rosa roxburghii

Cross-Links

• PubChem: 95168
• NPASS: NPC201731
• ChEMBL: CHEMBL238188
• LOTUS: LTS0236700
• wikiData: Q27107586