Pseudobaptigenin

Details

• Internal ID: 853f7e2a-6297-4d08-a05b-9acca992aeff
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-2-enes > Isoflavones
• IUPAC Name: 3-(1,3-benzodioxol-5-yl)-7-hydroxychromen-4-one
• SMILES (Canonical): C1OC2=C(O1)C=C(C=C2)C3=COC4=C(C3=O)C=CC(=C4)O
• SMILES (Isomeric): C1OC2=C(O1)C=C(C=C2)C3=COC4=C(C3=O)C=CC(=C4)O
• InChI: InChI=1S/C16H10O5/c17-10-2-3-11-14(6-10)19-7-12(16(11)18)9-1-4-13-15(5-9)21-8-20-13/h1-7,17H,8H2
• InChI Key: KNJNBKINYHZUGC-UHFFFAOYSA-N
• Popularity: 36 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₀O₅
• Molecular Weight: 282.25 g/mol
• Exact Mass: 282.05282342 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Psi-baptigenin
• 90-29-9
• .psi.-Baptigenin
• NSC-100796
• 7-Hydroxy-3',4'-methylenedioxyisoflavone
• UNII-78RRL4HLL9
• 78RRL4HLL9
• PSEUDOBABTIGEN
• CHEBI:8602
• pseudobaptisin aglycone
• 7-hydroxy-3',4'-(methylenedioxy)isoflavone
• 3-(1,3-Benzodioxol-5-yl)-7-hydroxy-4H-chromen-4-one
• 3-(1,3-benzodioxol-5-yl)-7-hydroxy-4H-1-benzopyran-4-one
• NSC 100796
• 3-(1,3-benzodioxol-5-yl)-7-hydroxychromen-4-one
• 7-Hydroxy-3', 4'-methylenedioxyisoflavone
• CHEMBL486176
• 3-(benzo[d][1,3]dioxol-5-yl)-7-hydroxy-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 3-(1,3-benzodioxol-5-yl)-7-hydroxy-
• DTXSID70237982
• NSC100796
• psedobaptigenin
• pseudobaptogenin
• y-Baptigenin
• Spectrum_001748
• Spectrum4_001241
• Spectrum5_001868
• PSEUDOBAPTIGENIN(RG)
• SCHEMBL73016
• KBioGR_001762
• KBioSS_002228
• PSEUDOBAPTIGENIN [MI]
• KBio2_002228
• KBio2_004796
• KBio2_007364
• DTXCID20160473
• Isoflavone,4'-(methylenedioxy)-
• BDBM50299414
• CCG-40053
• LMPK12050053
• AKOS000277200
• FT-0704675
• 7-Hydroxy-3',4'-(methylenedioxy)-Isoflavone
• N13311
• Q7254529
• 3-(1,3-benzodioxol-5-yl)-7-hydroxy-chromen-4-one
• 4H-1-Benzopyran-4-one,3-benzodioxol-5-yl)-7-hydroxy-
• 3-(2H-1,3-benzodioxol-5-yl)-7-hydroxy-4H-chromen-4-one
• 3-(1,3-Benzodioxol-5-yl)-7-hydroxy-4H-1-benzopyran-4-one, 9CI
• 77069-09-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9862	98.62%
Caco-2	+	0.6269	62.69%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8090	80.90%
OATP2B1 inhibitior	-	0.7224	72.24%
OATP1B1 inhibitior	+	0.9363	93.63%
OATP1B3 inhibitior	+	0.9114	91.14%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6915	69.15%
P-glycoprotein inhibitior	-	0.5883	58.83%
P-glycoprotein substrate	-	0.8991	89.91%
CYP3A4 substrate	+	0.5221	52.21%
CYP2C9 substrate	-	0.8137	81.37%
CYP2D6 substrate	-	0.8267	82.67%
CYP3A4 inhibition	+	0.6703	67.03%
CYP2C9 inhibition	+	0.6056	60.56%
CYP2C19 inhibition	-	0.5853	58.53%
CYP2D6 inhibition	-	0.6764	67.64%
CYP1A2 inhibition	+	0.6250	62.50%
CYP2C8 inhibition	-	0.5964	59.64%
CYP inhibitory promiscuity	+	0.5599	55.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5294	52.94%
Eye corrosion	-	0.9880	98.80%
Eye irritation	+	0.7278	72.78%
Skin irritation	-	0.5477	54.77%
Skin corrosion	-	0.9646	96.46%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8207	82.07%
Micronuclear	+	0.8874	88.74%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7912	79.12%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6262	62.62%
Acute Oral Toxicity (c)	II	0.4162	41.62%
Estrogen receptor binding	+	0.9531	95.31%
Androgen receptor binding	+	0.9550	95.50%
Thyroid receptor binding	+	0.6657	66.57%
Glucocorticoid receptor binding	+	0.8174	81.74%
Aromatase binding	+	0.9061	90.61%
PPAR gamma	+	0.8836	88.36%
Honey bee toxicity	-	0.8533	85.33%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9440	94.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	8900 nM; 8900 nM; 8900 nM	EC50; EC50; EC50	PMID: 26616289; PMID: 23265844; PMID: 19807106
CHEMBL3979	Q03181	Peroxisome proliferator-activated receptor delta	22340 nM	EC50	PMID: 23265844
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	26940 nM; 26940 nM; 26940 nM	EC50; EC50; EC50	PMID: 19807106; PMID: 26616289; PMID: 23265844

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.79%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.94%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.11%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.21%	96.77%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	91.70%	93.24%
CHEMBL242	Q92731	Estrogen receptor beta	91.27%	98.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.08%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.07%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.06%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.60%	86.33%
CHEMBL3438	Q05513	Protein kinase C zeta	86.79%	88.48%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.27%	99.15%
CHEMBL1929	P47989	Xanthine dehydrogenase	84.64%	96.12%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.48%	95.53%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.35%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.30%	99.23%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	82.46%	85.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.40%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.35%	93.40%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.86%	80.78%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.59%	80.96%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.21%	90.71%

Plants that contains it

• Abies alba
• Abies pinsapo subsp. marocana
• Ampelocera edentula
• Andira inermis
• Angelica acutiloba
• Arnica mollis
• Brassica carinata
• Bryonia alba
• Carpha glomerata
• Cicer arietinum
• Croton gratissimus
• Cyanostegia angustifolia
• Dactylorhiza viridis
• Dalbergia frutescens
• Dalbergia spruceana
• Dermatophyllum secundiflorum
• Diplopterygium glaucum
• Eucalyptus resinifera
• Euphrasia nana
• Eurycoma harmandiana
• Ixeris japonica
• Lysimachia fordiana
• Maackia amurensis
• Millettia griffoniana
• Orthosiphon aristatus
• Oxytropis falcata
• Pongamia pinnata
• Pterocarpus marsupium
• Pterolobium hexapetalum
• Ranunculus asiaticus
• Remirea maritima
• Sinapis alba
• Solanum lanceolatum
• Sophora alopecuroides
• Spatholobus suberectus
• Styphnolobium japonicum
• Trifolium pratense
• Viburnum erubescens
• Wikstroemia indica
• Xanthorhiza simplicissima

Cross-Links

• PubChem: 5281805
• NPASS: NPC35544
• ChEMBL: CHEMBL486176
• LOTUS: LTS0178079
• wikiData: Q7254529