Pomiferin

Details

• Internal ID: eb485e6d-7f5a-4cc2-8c1b-a47228d74c76
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 3-(3,4-dihydroxyphenyl)-5-hydroxy-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)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C3C(=C1O)C(=O)C(=CO3)C4=CC(=C(C=C4)O)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C25H24O6/c1-13(2)5-7-15-21(28)20-22(29)17(14-6-8-18(26)19(27)11-14)12-30-24(20)16-9-10-25(3,4)31-23(15)16/h5-6,8-12,26-28H,7H2,1-4H3
• InChI Key: GHCZYXUOYFOXIP-UHFFFAOYSA-N
• Popularity: 45 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₆
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.15728848 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.27
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 572-03-2
• CHEBI:8329
• NSC5113
• NSC-5113
• UNII-74YIS40APM
• 74YIS40APM
• MLS002701889
• 3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methyl-2-butenyl)-4H,8H-pyrano[2,3-f]chromen-4-one
• 3-(3,4-dihydroxyphenyl)-5-hydroxy-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, 3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methyl-2-butenyl)-
• AI3-22130
• Spectrum_000295
• 3'-HYDROXYOSAJIN
• POMIFERIN [INCI]
• Spectrum2_000799
• Spectrum3_000685
• Spectrum4_001808
• Spectrum5_000515
• NCIStruc1_001168
• NCIStruc2_001049
• BSPBio_002409
• KBioGR_002419
• KBioSS_000775
• SPECTRUM201580
• DivK1c_000996
• SPBio_000938
• CHEMBL393136
• SCHEMBL8059171
• HMS503G13
• KBio1_000996
• KBio2_000775
• KBio2_003343
• KBio2_005911
• KBio3_001629
• DTXSID00205831
• NCI5113
• NINDS_000996
• HMS1923A09
• HY-N4315
• BDBM50476976
• CCG-36078
• CCG-37331
• LMPK12050244
• NCGC00013053
• AKOS037515007
• SDCCGMLS-0066466.P001
• IDI1_000996
• NCGC00013053-02
• NCGC00013053-03
• NCGC00013053-04
• NCGC00013053-05
• NCGC00013053-06
• NCGC00095220-01
• NCGC00095220-02
• NCGC00095220-03
• NCGC00178667-01
• 3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)-4H,8H-pyrano(2,3-h)chromen-4-one
• NCI60_004233
• SMR001565475
• CS-0032736
• SR-05000002658
• SR-05000002658-1
• BRD-K50660510-001-04-0
• Q25323752
• 3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)-4H,8H- pyrano[2,3-h]chromen-4-one
• 4H,2-b:3,4-b']dipyran-4-one, 3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methyl-2-buten-1-yl)-
• 4H,8H-BENZO(1,2-B:3,4-B')DIPYRAN-4-ONE, 3-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-8,8-DIMETHYL-6-(3-METHYL-2-BUTEN-1-YL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9882	98.82%
Caco-2	-	0.6130	61.30%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7608	76.08%
OATP2B1 inhibitior	-	0.5679	56.79%
OATP1B1 inhibitior	+	0.9424	94.24%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8421	84.21%
P-glycoprotein inhibitior	+	0.7245	72.45%
P-glycoprotein substrate	-	0.6326	63.26%
CYP3A4 substrate	+	0.6399	63.99%
CYP2C9 substrate	-	0.6077	60.77%
CYP2D6 substrate	-	0.8218	82.18%
CYP3A4 inhibition	-	0.8762	87.62%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.8848	88.48%
CYP2C8 inhibition	+	0.7225	72.25%
CYP inhibitory promiscuity	+	0.6439	64.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6657	66.57%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.4825	48.25%
Skin irritation	-	0.7277	72.77%
Skin corrosion	-	0.9194	91.94%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7138	71.38%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7311	73.11%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6005	60.05%
Acute Oral Toxicity (c)	III	0.6482	64.82%
Estrogen receptor binding	+	0.9430	94.30%
Androgen receptor binding	+	0.8424	84.24%
Thyroid receptor binding	+	0.6948	69.48%
Glucocorticoid receptor binding	+	0.8500	85.00%
Aromatase binding	+	0.7548	75.48%
PPAR gamma	+	0.8875	88.75%
Honey bee toxicity	-	0.7130	71.30%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	562.3 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	12589.3 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3468	P55210	Caspase-7	39810.7 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	1995.26 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	3162.28 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	13340 nM	AC50	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	3981.1 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	28183.8 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	25118.9 nM; 12589.3 nM; 3548.1 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	35481.3 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	10000 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	99.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.73%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	98.10%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.53%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.40%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.38%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.27%	94.73%
CHEMBL3922	P50579	Methionine aminopeptidase 2	89.41%	97.28%
CHEMBL1937	Q92769	Histone deacetylase 2	89.19%	94.75%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.92%	91.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.90%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	87.85%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.37%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.15%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.02%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.46%	91.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.56%	96.12%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.44%	89.34%
CHEMBL4208	P20618	Proteasome component C5	80.06%	90.00%

Plants that contains it

• Euphorbia micractina
• Flemingia macrophylla
• Flemingia prostrata
• Maclura pomifera
• Millettia pachycarpa
• Rosa roxburghii

Cross-Links

• PubChem: 4871
• NPASS: NPC282307
• ChEMBL: CHEMBL393136
• LOTUS: LTS0000599
• wikiData: Q25323752