Pachyrrhizin

Details

• Internal ID: 894c39ca-ae80-42d7-a651-f3db0a05b01d
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-3-enes > Isoflav-3-enones
• IUPAC Name: 6-(6-methoxy-1,3-benzodioxol-5-yl)furo[3,2-g]chromen-7-one
• SMILES (Canonical): COC1=CC2=C(C=C1C3=CC4=C(C=C5C(=C4)C=CO5)OC3=O)OCO2
• SMILES (Isomeric): COC1=CC2=C(C=C1C3=CC4=C(C=C5C(=C4)C=CO5)OC3=O)OCO2
• InChI: InChI=1S/C19H12O6/c1-21-16-8-18-17(23-9-24-18)6-12(16)13-5-11-4-10-2-3-22-14(10)7-15(11)25-19(13)20/h2-8H,9H2,1H3
• InChI Key: PENSQRMNZZWMGV-UHFFFAOYSA-N
• Popularity: 26 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₂O₆
• Molecular Weight: 336.30 g/mol
• Exact Mass: 336.06338810 g/mol
• Topological Polar Surface Area (TPSA): 67.10 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.94
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Neorautone
• 10091-01-7
• Pachyrhizin
• 3F597EPM0S
• 6-(6-methoxy-1,3-benzodioxol-5-yl)furo[3,2-g]chromen-7-one
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 6-(6-methoxy-1,3-benzodioxol-5-yl)-
• NSC 404570
• NSC-404570
• 6-(6-Methoxy-1,3-benzodioxol-5-yl)-7H-furo(3,2-g)(1)benzopyran-7-one
• 7H-Furo[3,2-g][1]benzopyran-7-one, 6-(6-methoxy-1,3-benzodioxol-5-yl)-
• pachyrrizine
• NSC404570
• Spectrum_001845
• SpecPlus_000199
• Spectrum2_000410
• Spectrum3_000875
• Spectrum4_000715
• Spectrum5_000921
• UNII-3F597EPM0S
• BSPBio_002549
• KBioGR_001269
• KBioSS_002355
• SPECTRUM201602
• DivK1c_006295
• SPBio_000340
• CHEMBL479689
• SCHEMBL12062103
• KBio1_001239
• KBio2_002352
• KBio2_004920
• KBio2_007488
• KBio3_002049
• DTXSID10143573
• PACHYRRHIZIN (PACHYRHIZUS)
• CHEBI:108580
• HMS1923A15
• CCG-38676
• LMPK12160013
• SDCCGMLS-0066383.P001
• NCGC00095223-01
• NCGC00095223-02
• NCGC00095223-03
• NCGC00095223-04
• NCGC00178606-01
• SR-05000002599
• 6-(2-Methoxy-4,5-methylenedioxyphenyl)furocoumarin
• SR-05000002599-1
• 7H-Furo[3, 6-(6-methoxy-1,3-benzodioxol-5-yl)-
• BRD-K02070226-001-02-0
• BRD-K02070226-001-03-8
• Q27187505
• 6-(2-Methoxy-4,5-methylenedioxyphenyl)-7H-furo[3,2-g][1]benzopyran-7-one
• 6-(6-methoxy-1,3-benzodioxol-5-yl)-7-furo[3,2-g][1]benzopyranone
• 6-(6-Methoxy-1,3-benzodioxol-5-yl)-7H-furo[3,2-g][1]benzopyran-7-one, 9CI
• 5-BENZOFURANACRYLIC ACID, 6-HYDROXY-.ALPHA.-(2-METHOXY-4,5-(METHYLENEDIOXY)PHENYL)-, .DELTA.-LACTONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	+	0.6873	68.73%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7601	76.01%
OATP2B1 inhibitior	-	0.8666	86.66%
OATP1B1 inhibitior	+	0.9510	95.10%
OATP1B3 inhibitior	+	0.9840	98.40%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6798	67.98%
P-glycoprotein inhibitior	+	0.8733	87.33%
P-glycoprotein substrate	-	0.7243	72.43%
CYP3A4 substrate	+	0.5133	51.33%
CYP2C9 substrate	-	0.8464	84.64%
CYP2D6 substrate	-	0.8373	83.73%
CYP3A4 inhibition	+	0.9290	92.90%
CYP2C9 inhibition	+	0.9213	92.13%
CYP2C19 inhibition	+	0.9644	96.44%
CYP2D6 inhibition	+	0.7467	74.67%
CYP1A2 inhibition	+	0.7104	71.04%
CYP2C8 inhibition	-	0.7588	75.88%
CYP inhibitory promiscuity	+	0.9403	94.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4141	41.41%
Eye corrosion	-	0.9698	96.98%
Eye irritation	-	0.8179	81.79%
Skin irritation	-	0.7125	71.25%
Skin corrosion	-	0.9625	96.25%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6702	67.02%
Micronuclear	+	0.8074	80.74%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7663	76.63%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.6567	65.67%
Acute Oral Toxicity (c)	III	0.7452	74.52%
Estrogen receptor binding	+	0.9219	92.19%
Androgen receptor binding	+	0.7921	79.21%
Thyroid receptor binding	-	0.5156	51.56%
Glucocorticoid receptor binding	+	0.8429	84.29%
Aromatase binding	+	0.6933	69.33%
PPAR gamma	+	0.7144	71.44%
Honey bee toxicity	-	0.8248	82.48%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9349	93.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4801	P29466	Caspase-1	31622.8 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	19952.6 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	398.1 nM; 398.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.68%	96.77%
CHEMBL2581	P07339	Cathepsin D	95.94%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.03%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.15%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.68%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.50%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.96%	96.00%
CHEMBL240	Q12809	HERG	85.75%	89.76%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.15%	90.71%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.14%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.16%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.08%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.88%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.90%	99.17%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.25%	82.67%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.67%	92.38%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.64%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.23%	92.62%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.03%	94.03%

Plants that contains it

• Begonia glabra
• Neorautanenia mitis
• Pachyrhizus erosus
• Pachyrhizus tuberosus
• Pogostemon cablin

Cross-Links

• PubChem: 101277
• NPASS: NPC72455
• ChEMBL: CHEMBL479689
• LOTUS: LTS0151185
• wikiData: Q27187505